obtainednano5
nano5 时间:2021-01-17 阅读:()
SupportingInformationAmulti-componentdominoreactionforthedirectaccesstopolyfunctionalizedindolesviaintermolecularallylicesterificationandindolationBoJiang,1Mian-ShuaiYi,1FengShi,1Shu-JiangTu,*,1SureshPindi,2PatrickMcDowell2andGuigenLi*,21SchoolofChemistryandChemicalEngineering,JiangsuKeyLaboratoryofGreenSyntheticChemistryforFunctionalMaterials,XuzhouNormalUniversity,P.
R.
China;and2DepartmentofChemistryandBiochemistry,TexasTechUniversity,Lubbock,TX79409-1061ExperimentalGeneralinformationMicrowaveirradiationwascarriedoutwithInitiator2.
5MicrowaveSynthesizersfromBiotage,Uppsala,Sweden.
Meltingpointsweredeterminedinopencapillariesandwereuncorrected.
IRspectraweretakenonaFT-IR-Tensor27spectrometerinKBrpelletsandreportedincm-1.
1HNMRspectraweremeasuredonaBrukerDPX400MHzspectrometerinDMSO-d6withchemicalshift(δ)giveninppmrelativetoTMSasinternalstandard[(s=singlet,d=doublet,t=triplet,brs=broadsinglet,m=multiplet),couplingconstant(Hz)].
HRMS(ESI)wasdeterminedbyusingmicroTOF-QⅡHRMS/MSinstrument(BRUKER).
X-RaycrystallographicanalysiswasperformedwithaSiemensSMARTCCDandaSiemensP4diffractometer.
Fig1,X-rayStructureofindoles4aFig2,X-rayStructureofbis-indoles5aCrystaldatafor4a:C25H25NO3,Mr=387.
46,Monoclinic,a=8.
6760(8),b=12.
8793(13),c=9.
4794(11),U=1045.
73(19)3,T=298(2)K,spacegroupP2(1),Z=2,5349reflectionsmeasured,1936unique(Rint=0.
0428)whichwereusedinallcalculation.
ThefinalwR(F2)was0.
0638(alldata)Crystaldatafor5a:C42H34N2O2,Mr=598.
71,Triclinic,a=10.
0878(13),b=11.
1881(13),c=15.
2089(16),U=1594.
8(3)3,T=298(2)K,spacegroupP-1,Z=2,8283reflectionsmeasured,5520unique(Rint=0.
1165)whichwereusedinallcalculation.
ThefinalwR(F2)was0.
2184(alldata)Generalprocedureforthesynthesisofindoles4Exampleforthesynthesisof4a:4,5,6,7-tetrahydro-6,6-dimethyl-4-oxo-1,2-diphenyl-1H-indol-7-ylacetateMicrowaveHeating:phenylglyoxalmonohydrate(1a,1.
1mmol,0.
17g,1.
1equiv.
)wasintroducedina10-mLInitiatorTMreactionvial,3-(p-tolylamino)-5,5-dimethylcyclohex-2-enone(2a,1.
0mmol,0.
23g,1.
0equiv.
)andaceticacid(3a,2mL,excess.
)werethensuccessivelyadded.
Subsequently,thereactionvialwascappedandthenpre-stiringfor20second.
Themixturewasirradiated(Time:15min,Temperature:120oC;AbsorptionLevel:High;FixedHoldTime)untilTLC(petroleumether:acetone4:1)revealedthatconversionofthestartingmaterial2awascomplete.
Thereactionmixturewasthencooledtoroomtemperatureandthendilutedwithcoldwater(20ml).
ThesolidproductwascollectedbyBüchnerfiltrationandwaspurifiedbyflashcolumnchromatography(silicagel,mixturesofpetroleumether/acetone,9:1,v/v)toaffordthedesiredpureindoles4aaswhitesolid(Mp:124-126oC).
IR(KBr,,cm-1):1739,1667,1495,1465,1371,1229,1051,1015,968,766.
1HNMR(400MHz,DMSO)δ:7.
50-7.
38(m,4H,ArH),7.
23-7.
19(m,3H,ArH),7.
15-7.
12(m,2H,ArH),6.
70(s,1H,CH),5.
58(s,1H,OCH),2.
64(d,J=15.
6Hz,1H,CH2),2.
20(d,J=16.
4Hz,1H,CH2),1.
84(s,3H,CH3),1.
06(s,3H,CH3),0.
93(s,3H,CH3).
13CNMR(100MHz,DMSO)δ:192.
1,168.
9,140.
0,137.
5,136.
4,131.
0,129.
1,128.
2,128.
1,127.
4,120.
7,104.
6,68.
4,47.
7,30.
7,25.
6,24.
8,20.
2.
HRMS(ESI):m/zcalcdfor:C24H24NO3,374.
1751,found:374.
1757.
Scopeofmulticomponentdominoreaction1-(4-Fluorophenyl)-4,5,6,7-tetrahydro-6,6-dimethyl-4-oxo-2-phenyl-1H-indol-7-ylacetate4bThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,9:1,v/v)(Mp:190-192oC).
IR(KBr,,cm-1):1744,1668,1509,1464,1371,1227,1050,1016,968,855.
1HNMR(400MHz,DMSO)δ:7.
52(s,1H,ArH),7.
53(d,J=8.
0Hz,1H,ArH),7.
24-7.
21(m,4H,ArH),7.
16-7.
14(m,3H,ArH),6.
69(s,1H,CH),5.
56(s,1H,OCH),2.
65(d,J=16.
4Hz,1H,CH2),2.
20(d,J=16.
4Hz,1H,CH2),1.
88(s,3H,CH3),1.
07(s,3H,CH3),0.
94(s,3H,CH3).
13CNMR(100MHz,DMSO)δ:192.
0,169.
0,161.
7(1JCF=244.
5Hz),140.
1,137.
6,132.
6(4JCF=2.
7Hz),130.
8,130.
5(3JCF=9.
4Hz),128.
3,128.
2,127.
5,120.
7,116.
1(2JCF=24.
1Hz),112.
6,104.
5,68.
2,47.
6,25.
5,24.
7,20.
1.
HRMS(ESI):m/zcalcdfor:C24H22FNNaO3,414.
1476,found:414.
1481.
1-(4-Bromophenyl)-4,5,6,7-tetrahydro-6,6-dimethyl-4-oxo-2-phenyl-1H-indol-7-ylacetate4cThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,9:1,v/v)(Mp:158-160oC).
IR(KBr,,cm-1):1739,1664,1492,1457,1225,1048,1017,900,846.
1HNMR(400MHz,DMSO)δ:7.
69(s,1H,ArH),7.
57(d,J=8.
0Hz,1H,ArH),7.
39(d,J=7.
2Hz,1H,ArH),7.
27-7.
22(m,3H,ArH),7.
16-7.
14(m,2H,ArH),7.
07(d,J=5.
6Hz,1H,ArH),6.
69(s,1H,CH),5.
57(s,1H,OCH),2.
64(d,J=16.
4Hz,1H,CH2),2.
21(d,J=16.
4Hz,1H,CH2),1.
88(s,3H,CH3),1.
06(s,3H,CH3),0.
94(s,3H,CH3).
13CNMR(100MHz,DMSO)δ:192.
1,169.
1,140.
0,137.
5,135.
7,130.
8,130.
4,128.
4,128.
3,127.
6,122.
2,120.
9,104.
8,68.
4,47.
7,25.
5,24.
8,20.
2.
HRMS(ESI):m/zcalcdfor:C24H22BrNNaO3,474.
0676,found:474.
0652.
4,5,6,7-tetrahydro-6,6-dimethyl-4-oxo-2-phenyl-1-p-tolyl-1H-indol-7-ylacetate4dThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,9:1,v/v)(Mp:>198-200oC).
IR(KBr,,cm-1):1737,1661,1515,1458,1228,1049,1020,966,831,772.
1HNMR(400MHz,DMSO)δ:7.
27-7.
24(m,1H,ArH),7.
22-7.
18(m,5H,ArH),7.
15-7.
13(m,2H,ArH),7.
01(d,J=7.
6Hz,1H,ArH),6.
67(s,1H,CH),5.
54(s,1H,OCH),2.
64(d,J=16.
8Hz,1H,CH2),2.
33(s,3H,CH3),2.
22(d,J=16.
4Hz,1H,CH2),1.
89(s,3H,CH3),1.
04(s,3H,CH3),0.
93(s,3H,CH3).
13CNMR(100MHz,DMSO)δ:192.
0,169.
0,140.
1,138.
4,137.
4,133.
7,131.
0,128.
2,128.
1,127.
8,127.
3,120.
6,104.
5,68.
4,47.
6,25.
4,24.
8,20.
6,20.
2.
HRMS(ESI):m/zcalcdfor:C25H25NNaO3,410.
1727,found:410.
1736.
4,5,6,7-Tetrahydro-6,6-dimethyl-4-oxo-1,2-diphenyl-1H-indol-7-ylpropionate4eThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,9:1,v/v)(Mp:123-125oC).
IR(KBr,,cm-1):1741,1666,1498,1459,1165,1078,809,763,701.
1HNMR(400MHz,DMSO)δ:7.
48-7.
36(m,3H,ArH),7.
36(d,J=14Hz,1H,ArH),7.
21-7.
12(m,5H,ArH),7.
07(d,J=14Hz,1H,ArH),6.
70(s,1H,CH),5.
64(s,1H,OCH),2.
83(d,J=16.
4Hz,1H,CH2),2.
23-2.
03(m,2H,CH2),2.
18(d,J=16.
4Hz,1H,CH2),1.
07(s,3H,CH3),0.
92(s,3H,CH3),0.
87(t,J=14.
8Hz,3H,CH3).
13CNMR(100MHz,DMSO)δ:192.
0,172.
1,140.
0,137.
4,136.
3,131.
0,128.
9,128.
2,128.
1,127.
3,120.
7,104.
5,68.
2,47.
7,26.
3,25.
6,24.
7,8.
8.
HRMS(ESI):m/zcalcdfor:C25H26NO3,388.
1908,found:388.
1912.
1-(4-Fluorophenyl)-4,5,6,7-tetrahydro-6,6-dimethyl-4-oxo-2-phenyl-1H-indol-7-ylpropionate4fThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,9:1,v/v)(Mp:130-132oC).
IR(KBr,,cm-1):1744,1672,1509,1463,1368,1157,1050,917,857,764.
1HNMR(400MHz,DMSO)δ:7.
55(s,1H,ArH),7.
34(d,J=8.
4Hz,1H,ArH),7.
27-7.
19(m,4H,ArH),7.
16-7.
14(m,3H,ArH),6.
69(s,1H,CH),5.
63(s,1H,OCH),2.
64(d,J=16.
4Hz,1H,CH2),2.
27-2.
05(m,2H,CH2),2.
17(d,J=16.
4Hz,1H,CH2),1.
08(s,3H,CH3),0.
93(s,3H,CH3),0.
88(t,J=14.
8Hz,3H,CH3).
13CNMR(100MHz,DMSO)δ:192.
1,172.
3,159.
4(1JCF=228.
6Hz),140.
2,137.
7,132.
7(4JCF=2.
9Hz),130.
9,130.
5(3JCF=8.
3Hz),128.
3,128.
2,127.
5,120.
8,116.
2(2JCF=22.
0Hz),104.
6,68.
1,47.
8,38.
5,26.
4,25.
6,24.
7,8.
9.
HRMS(ESI):m/zcalcdfor:C25H24FNNaO3,428.
1633,found:428.
1640.
1-(4-chlorophenyl)-4,5,6,7-tetrahydro-6,6-dimethyl-4-oxo-2-phenyl-1H-indol-7-ylpropionate4gThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,9:1,v/v)(Mp:138-140oCoC).
IR(KBr,,cm-1):1746,1664,1496,1464,1200,1055,996,767,699.
1HNMR(400MHz,DMSO)δ:7.
59-7.
53(m,2H,ArH),7.
41(d,J=8.
0Hz,1H,ArH),7.
28-7.
22(m,3H,ArH),7.
21-7.
14(m,3H,ArH),7.
08(d,J=8.
4Hz,1H,ArH),6.
70(s,1H,CH),5.
66(s,1H,OCH),2.
63(d,J=16.
4Hz,1H,CH2),2.
25-2.
04(m,2H,CH2),2.
23(d,J=16.
4Hz,1H,CH2),1.
07(s,3H,CH3),0.
93(s,3H,CH3),0.
89(t,J=7.
2Hz,3H,CH3).
13CNMR(100MHz,DMSO)δ:192.
1,172.
3,137.
6,135.
3,133.
6,130.
8,128.
4,128.
3,127.
6,124.
1,104.
8,68.
2,47.
8,30.
7,26.
4,25.
7,24.
6,8.
8.
HRMS(ESI):m/zcalcdfor:C25H24ClNNaO3,444.
1337,found:444.
1345.
1-(4-bromophenyl)-4,5,6,7-tetrahydro-6,6-dimethyl-4-oxo-2-phenyl-1H-indol-7-ylpropionate4hThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,9:1,v/v)(Mp:122-123oC).
IR(KBr,,cm-1):1747,1674,1489,1461,1200,1151,1050,1018,763.
1HNMR(400MHz,DMSO)δ:7.
70(d,J=8.
0Hz,1H,ArH),7.
55(d,J=8.
0Hz,1H,ArH),7.
44(d,J=8.
0Hz,1H,ArH),7.
28-7.
23(m,3H,ArH),7.
16-7.
14(m,2H,ArH),7.
01(d,J=7.
6Hz,1H,ArH),6.
69(s,1H,CH),5.
66(s,1H,OCH),2.
62(d,J=16.
4Hz,1H,CH2),2.
27-2.
04(m,2H,CH2),2.
19(d,J=16.
8Hz,1H,CH2),1.
07(s,3H,CH3),0.
93(s,3H,CH3),0.
88(t,J=14.
8Hz,3H,CH3).
13CNMR(100MHz,DMSO)δ:192.
3,172.
4,140.
1,137.
5,135.
7,130.
7,128.
4,128.
3,127.
6,122.
1,120.
9,104.
8,68.
2,47.
9,30.
7,26.
4,25.
6,24.
6,8.
8.
HRMS(ESI):m/zcalcdfor:C25H24BrNNaO3,488.
0832,found:488.
0850.
4,5,6,7-tetrahydro-6,6-dimethyl-4-oxo-2-phenyl-1-p-tolyl-1H-indol-7-ylpropionate4iThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,9:1,v/v)(Mp:127-128oC).
IR(KBr,,cm-1):1739,1671,1516,1457,1164,1076,1048,812,765,700.
1HNMR(400MHz,DMSO)δ:7.
26-7.
24(m,2H,ArH),7.
22-7.
19(m,3H,ArH),7.
15-7.
13(m,3H,ArH),6.
95(d,J=6.
4Hz,1H,ArH),6.
67(s,1H,CH),5.
62(s,1H,OCH),2.
62(d,J=16.
4Hz,1H,CH2),2.
33(s,3H,CH3),2.
24-2.
05(m,2H,CH2),2.
21(d,J=16.
4Hz,1H,CH2),1.
05(s,3H,CH3),0.
92(s,3H,CH3),0.
89(t,J=7.
6Hz,3H,CH3).
13CNMR(100MHz,DMSO)δ:192.
0,172.
2,140.
1,138.
3,137.
4,133.
8,131.
0,128.
2,128.
1,127.
8,127.
7,127.
3,120.
6,104.
5,68.
3,47.
7,26.
4,25.
5,24.
8,20.
6,8.
8.
HRMS(ESI):m/zcalcdfor:C26H27NNaO3,424.
1884,found:424.
1889.
4,5,6,7-tetrahydro-1-(4-methoxyphenyl)-6,6-dimethyl-4-oxo-2-phenyl-1H-indol-7-ylpropionate4jThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,9:1,v/v)(Mp:186-187oC).
IR(KBr,,cm-1):1743,1668,1512,1466,1252,1052,1030,917,850,761,.
1HNMR(400MHz,DMSO)δ:7.
33(d,J=8.
0Hz,1H,ArH),7.
23-7.
15(m,5H,ArH),7.
01-7.
00(m,2H,ArH),6.
88(d,J=8.
0Hz,1H,ArH),6.
67(s,1H,CH),5.
61(s,1H,OCH),2.
63(d,J=16.
4Hz,1H,CH2),2.
28-2.
09(m,2H,CH2),2.
19(d,J=16.
4Hz,1H,CH2),1.
06(s,3H,CH3),0.
92(s,3H,CH3),0.
89(t,J=7.
2Hz,3H,CH3).
13CNMR(100MHz,DMSO)δ:192.
0,172.
2,159.
1,140.
3,137.
6,131.
1,129.
3,129.
2,128.
9,128.
2,128.
1,127.
3,120.
4,114.
4,104.
3,68.
2,55.
3,47.
7,26.
4,25.
6,24.
7,8.
8.
HRMS(ESI):m/zcalcdfor:C26H27NNaO4,440.
1833,found:440.
1831.
1-(4-chlorophenyl)-4,5,6,7-tetrahydro-6,6-dimethyl-4-oxo-2-phenyl-1H-indol-7-ylbutyrate4kThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,9:1,v/v)(Mp:147-149oC).
IR(KBr,,cm-1):1744,1674,1493,1463,1152,1049,853,762,727,698.
1HNMR(400MHz,DMSO)δ:7.
39(d,J=8.
0Hz,1H,ArH),7.
27-7.
21(m,3H,ArH),7.
15-7.
13(m,2H,ArH),7.
06(d,J=8.
0Hz,1H,ArH),6.
69(s,1H,CH),5.
67(s,1H,OCH),2.
62(d,J=16.
4Hz,1H,CH2),2.
24-1.
98(m,2H,CH2),2.
03(d,J=16.
4Hz,1H,CH2),1.
41-1.
35(m,2H,CH2),1.
08(s,3H,CH3),0.
93(s,3H,CH3),0.
89(t,J=14.
8Hz,3H,CH3).
13CNMR(100MHz,DMSO)δ:192.
1,171.
4,140.
0,137.
5,135.
3,133.
6,130.
8,128.
4,128.
3,127.
6,121.
0,104.
8,68.
2,47.
8,34.
7,30.
7,25.
6,24.
7,17.
6,13.
4.
HRMS(ESI):m/zcalcdfor:C26H27ClNO3,436.
1674,found:436.
1678.
1-(4-Bromophenyl)-4,5,6,7-tetrahydro-6,6-dimethyl-4-oxo-2-phenyl-1H-indol-7-ylbutyrate4lThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,9:1,v/v)(Mp:145-146oC).
IR(KBr,,cm-1):1744,1673,1489,1462,1150,1075,852,763,719,698.
1HNMR(400MHz,DMSO)δ:7.
71(d,J=7.
6Hz,1H,ArH),7.
53(d,J=7.
6Hz,1H,ArH),7.
46(d,J=7.
6Hz,1H,ArH),7.
28-7.
22(m,3H,ArH),7.
15-7.
13(m,2H,ArH),6.
99(d,J=7.
2Hz,1H,ArH),6.
69(s,1H,CH),5.
68(s,1H,OCH),2.
62(d,J=16.
4Hz,1H,CH2),2.
25-2.
15(m,2H,CH2),2.
20(d,J=16.
4Hz,1H,CH2),1.
43-1.
34(m,2H,CH2),1.
08(s,3H,CH3),0.
93(s,3H,CH3),0.
79(t,J=14.
8Hz,3H,CH3).
13CNMR(100MHz,DMSO)δ:192.
1,171.
4,140.
0,137.
5,135.
8,130.
8,130.
3,128.
4,127.
6,122.
1,121.
0,104.
9,68.
2,47.
8,34.
7,30.
7,25.
6,24.
7,17.
6,13.
4.
HRMS(ESI):m/zcalcdfor:C26H27BrNO3,480.
1169,found:480.
1167.
4,5,6,7-tetrahydro-6,6-dimethyl-4-oxo-2-phenyl-1-p-tolyl-1H-indol-7-ylbutyrate4mThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,9:1,v/v)(Mp:136-137oC).
IR(KBr,,cm-1):1739,1667,1516,1458,1410,1162,969,765,698.
1HNMR(400MHz,DMSO)δ:7.
27-7.
24(m,2H,ArH),7.
22-7.
19(m,3H,ArH),7.
18-7.
12(m,3H,ArH),6.
94(d,J=7.
6Hz,1H,ArH),6.
68(s,1H,CH),5.
63(s,1H,OCH),2.
63(d,J=16.
4Hz,1H,CH2),2.
32(s,3H,CH3),2.
22-2.
17(m,2H,CH2),2.
04(d,J=16.
0Hz,1H,CH2),1.
40-1.
38(m,2H,CH2),1.
05(s,3H,CH3),0.
92(s,3H,CH3),0.
80(t,J=14.
8Hz,3H,CH3).
13CNMR(100MHz,DMSO)δ:192.
1,171.
4,140.
1,137.
5,133.
8,131.
1,128.
3,127.
8,120.
7,104.
6,68.
3,47.
7,34.
8,30.
7,25.
7,20.
7,17.
6,13.
4.
HRMS(ESI):m/zcalcdfor:C27H29NNaO3,438.
2040,found:438.
2041.
4,5,6,7-tetrahydro-1-(4-methoxyphenyl)-6,6-dimethyl-4-oxo-2-phenyl-1H-indol-7-ylbutyrate4nThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasapaleyellowsolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,9:1,v/v)(Mp:127-128oC).
IR(KBr,,cm-1):1740,1669,1513,1465,1251,1156,850,760,697.
1HNMR(400MHz,DMSO)δ:7.
33(d,J=8.
0Hz,1H,ArH),7.
25-7.
23(m,5H,ArH),7.
03-6.
98(m,2H,ArH),6.
87(d,J=8.
0Hz,1H,ArH),6.
67(s,1H,CH),5.
62(s,1H,OCH),3.
76(s,3H,OCH3),2.
63(d,J=16.
8Hz,1H,CH2),2.
24-2.
03(m,2H,CH2),2.
19(d,J=16.
8Hz,1H,CH2),1.
44-1.
35(m,2H,CH2),1.
06(s,3H,CH3),0.
92(s,3H,CH3),0.
80(t,J=14.
4Hz,3H,CH3).
13CNMR(100MHz,DMSO)δ:192.
1,171.
4,159.
2,140.
3,137.
6,131.
1,129.
0,128.
3,127.
4,120.
5,114.
5,104.
4,68.
2,55.
4,34.
8,30.
7,25.
6,24.
9,17.
7,13.
4.
HRMS(ESI):m/zcalcdfor:C27H30NO4,432.
2170,found:432.
2154.
1-(4-fluorophenyl)-4,5,6,7-tetrahydro-6,6-dimethyl-4-oxo-2-phenyl-1H-indol-7-ylisobutyrate4oThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,9:1,v/v)(Mp:117-119oC).
IR(KBr,,cm-1):1735,1669,1513,1459,1150,1050,849,763,698.
1HNMR(400MHz,DMSO)δ:7.
59(s,1H,ArH),7.
37(d,J=8.
8Hz,1H,ArH),7.
27-7.
23(m,3H,ArH),7.
16-7.
14(m,3H,ArH),7.
06(s,1H,ArH),6.
70(s,1H,CH),5.
66(s,1H,OCH),2.
66(d,J=16.
4Hz,1H,CH2),2.
40-2.
33(m,1H,CH),2.
21(d,J=16.
4Hz,1H,CH2),1.
09(s,3H,CH3),1.
00(t,J=6.
8Hz,3H,CH3),0.
89(t,J=6.
8Hz,3H,CH3),0.
92(s,3H,CH3).
13CNMR(100MHz,DMSO)δ:192.
1,174.
6,161.
7(1JCF=244.
9Hz),140.
1,137.
6,132.
7(4JCF=2.
8Hz),130.
8,130.
4(3JCF=8.
0Hz),128.
3,127.
5,120.
8,116.
5(2JCF=22.
2Hz),112.
7,104.
7,68.
0,47.
7,33.
1,25.
6,24.
7,19.
1.
18.
4.
HRMS(ESI):m/zcalcdfor:C26H26FNNaO3,442.
1789,found:442.
1799.
1-(4-chlorophenyl)-4,5,6,7-tetrahydro-6,6-dimethyl-4-oxo-2-phenyl-1H-indol-7-ylisobutyrate4pThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,9:1,v/v)(Mp:165-166oC).
IR(KBr,,cm-1):1736,1673,1496,1455,1145,1093,852,769,702.
1HNMR(400MHz,DMSO)δ:7.
57(s,2H,ArH),7.
40(d,J=8.
0Hz,1H,ArH),7.
26-7.
14(m,5H,ArH),7.
02(d,J=8.
4Hz,1H,ArH),6.
70(s,1H,CH),5.
70(s,1H,OCH),2.
65(d,J=16.
4Hz,1H,CH2),2.
35-2.
30(m,1H,CH),2.
23(d,J=16.
4Hz,1H,CH2),1.
08(s,3H,CH3),1.
01(t,J=7.
2Hz,3H,CH3)0.
93(s,3H,CH3),0.
88(t,J=6.
8Hz,3H,CH3).
13CNMR(100MHz,DMSO)δ:206.
5,192.
1,174.
7,139.
9,137.
5,135.
7,130.
8,128.
3,127.
6,122.
0,121.
0,104.
9,68.
1,47.
8,33.
1,30.
7,25.
7,24.
6,19.
1.
18.
3.
HRMS(ESI):m/zcalcdfor:C26H27ClNO3,436.
1674,found:436.
1677.
1-(4-bromophenyl)-4,5,6,7-tetrahydro-6,6-dimethyl-4-oxo-2-phenyl-1H-indol-7-ylisobutyrate4qThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,9:1,v/v)(Mp:176-177oC).
IR(KBr,,cm-1):1736,1672,1494,1456,1411,1145,1048,850,767,700.
1HNMR(400MHz,DMSO)δ:7.
71(d,J=8.
4Hz,1H,ArH),7.
53-7.
48(m,2H,ArH),7.
26-7.
22(m,3H,ArH),7.
16-7.
14(m,2H,ArH),6.
95(d,J=8.
4Hz,1H,ArH),6.
70(s,1H,CH),5.
70(s,1H,OCH),2.
64(d,J=16.
4Hz,1H,CH2),2.
34-2.
30(m,H,CH),2.
23(d,J=16.
4Hz,1H,CH2),1.
08(s,3H,CH3),1.
00(t,J=7.
2Hz,3H,CH3),0.
88(t,J=6.
8Hz,3H,CH3)0.
92(s,3H,CH3).
13CNMR(100MHz,DMSO)δ:206.
5,192.
1,174.
7,139.
9,137.
5,135.
7,130.
8,128.
3,127.
6,122.
0,121.
0,104.
9,68.
1,47.
8,33.
1,30.
7,25.
7,24.
6,19.
1.
18.
3.
HRMS(ESI):m/zcalcdfor:C26H26BrNNaO3,502.
0989,found:502.
1005.
4,5,6,7-tetrahydro-6,6-dimethyl-4-oxo-2-phenyl-1-p-tolyl-1H-indol-7-ylisobutyrate4rThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,9:1,v/v)(Mp:162-164oC).
IR(KBr,,cm-1):1734,1670,1516,1456,1217,1145,1049,846,767,701.
1HNMR(400MHz,DMSO)δ:7.
29(m,2H,ArH),7.
24-7.
19(m,3H,ArH),7.
15-7.
13(m,3H,ArH),6.
90(d,J=6.
0Hz,1H,ArH),6.
70(s,1H,CH),5.
70(s,1H,OCH),2.
64(d,J=16.
4Hz,1H,CH2),2.
38-2.
34(m,1H,CH),2.
32(s,3H,CH3),2.
21(d,J=16.
4Hz,1H,CH2),1.
06(s,3H,CH3),1.
01(t,J=7.
2Hz,3H,CH3)0.
91(s,3H,CH3),0.
90(t,J=6.
8Hz,3H,CH3).
13CNMR(100MHz,DMSO)δ:206.
5,192.
1,174.
6,140.
0,137.
5,135.
3,133.
5,130.
8,128.
3,127.
6,121.
0,104.
9,68.
1,56.
3,47.
8,33.
1,30.
7,25.
7,24.
6,19.
1,18.
3.
HRMS(ESI):m/zcalcdfor:C27H30NO3,416.
2221,found:416.
2221.
4,5,6,7-tetrahydro-1-(4-methoxyphenyl)-6,6-dimethyl-4-oxo-2-phenyl-1H-indol-7-ylisobutyrate4sThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,9:1,v/v)(Mp:181-182oC).
IR(KBr,,cm-1):1734,1667,1514,1460,1250,1147,1028,834,768,700.
1HNMR(400MHz,DMSO)δ:7.
36(d,J=8.
4Hz,1H,ArH),7.
23-7.
21(m,3H,ArH),7.
16-7.
03(m,2H,ArH),7.
02(d,J=8.
0Hz,1H,ArH),6.
94(d,J=8.
0Hz,1H,ArH),6.
86(d,J=8.
8Hz,1H,ArH),6.
67(s,1H,CH),5.
63(s,1H,OCH),3.
76(s,3H,OCH3),2.
65(d,J=16.
4Hz,1H,CH2),2.
41-2.
34(m,2H,CH2),2.
19(d,J=16.
4Hz,1H,CH2),1.
06(s,3H,CH3),1.
02(t,J=6.
8Hz,3H,CH3),0.
91(t,J=6.
8Hz,3H,CH3)0.
92(s,3H,CH3).
13CNMR(100MHz,DMSO)δ:206.
5,174.
6,162.
4,159.
2,147.
6,141.
7,137.
6,128.
3,128.
2,127.
3,120.
6,104.
4,68.
1,55.
4,33.
1,30.
7,25.
6,24.
7,19.
2,18.
3.
HRMS(ESI):m/zcalcdfor:C27H30NO4,432.
2170,found:432.
2172.
2-(benzo[d][1,3]dioxol-5-yl)-1-(4-bromophenyl)-4,5,6,7-tetrahydro-6,6-dimethyl-4-oxo-1H-indol-7-ylacetate4tThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,9:1,v/v)(Mp:159-161oC).
IR(KBr,,cm-1):1737,1678,1494,1474,1221,1036,1016,803,728.
1HNMR(400MHz,DMSO)δ:7.
70(d,J=8.
0Hz,1H,ArH),7.
59(d,J=8.
0Hz,1H,ArH),7.
38(d,J=7.
6Hz,1H,ArH),7.
08(d,J=8.
0Hz,1H,ArH),6.
82-6.
75(m,1H,ArH),6.
72(s,1H,ArH),6.
61(s,1H,ArH),6.
59(s,1H,OCH),5.
98(s,2H,CH2),5.
54(s,1H,CH),2.
63(d,J=16.
4Hz,1H,CH2),2.
19(d,J=16.
4Hz,1H,CH2),1.
88(s,3H,CH3),1.
05(s,3H,CH3),0.
93(s,3H,CH3).
13CNMR(100MHz,DMSO)δ:192.
1,169.
1,147.
1,137.
3,135.
7,132.
2,130.
4,122.
5,119.
1,108.
8,104.
4,101.
2,25.
5,21.
0,20.
2.
HRMS(ESI):m/zcalcdfor:C25H23BrNO5,496.
0755,found:496.
0730.
2-(benzo[d][1,3]dioxol-5-yl)-1-(4-bromophenyl)-4,5,6,7-tetrahydro-6,6-dimethyl-4-oxo-1H-indol-7-ylpropionate4uThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,9:1,v/v)(Mp:162-164oC).
IR(KBr,,cm-1):1735,1679,1494,1476,1232,1201,1037,873,803,728.
1HNMR(400MHz,DMSO)δ:7.
71(d,J=8.
0Hz,1H,ArH),7.
57(d,J=8.
0Hz,1H,ArH),7.
43(d,J=8.
0Hz,1H,ArH),7.
02(d,J=8.
0Hz,1H,ArH),6.
81-6.
79(m,1H,ArH),6.
73(s,1H,ArH),6.
61(s,1H,ArH),6.
59(s,1H,OCH),5.
98(s,2H,CH2),5.
63(s,1H,CH),2.
60(d,J=16.
4Hz,1H,CH2),2.
22(d,J=16.
4Hz,1H,CH2),2.
24-2.
01(m,2H,CH2),1.
06(s,3H,CH3),0.
91(s,3H,CH3),0.
87(t,J=15.
2Hz,3H,CH3).
13CNMR(100MHz,DMSO)δ:192.
1,172.
3,151.
7,148.
4,139.
6,137.
3,135.
8,134.
4,122.
5,108.
8,101.
2,68.
3,26.
4,24.
6,17.
2,16.
3,8.
9.
HRMS(ESI):m/zcalcdfor:C26H24BrNaNO5,532.
0731,found:532.
0717.
2-(benzo[d][1,3]dioxol-5-yl)-1-(4-bromophenyl)-4,5,6,7-tetrahydro-6,6-dimethyl-4-oxo-1H-indol-7-ylbutyrate4vThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,9:1,v/v)(Mp:147-149oC).
IR(KBr,,cm-1):1728,1681,1494,1475,1231,1165,1036,838,803,728.
1HNMR(400MHz,DMSO)δ:7.
71(d,J=8.
4Hz,1H,ArH),7.
55(d,J=8.
4Hz,1H,ArH),7.
44(d,J=8.
4Hz,1H,ArH),7.
01(d,J=8.
4Hz,1H,ArH),6.
81-6.
79(m,1H,ArH),6.
72(s,1H,ArH),6.
60(s,1H,ArH),6.
58(s,1H,OCH),5.
98(s,2H,CH2),5.
64(s,1H,CH),2.
60(d,J=16.
4Hz,1H,CH2),2.
21(d,J=16.
4Hz,1H,CH2),2.
23-1.
97(m,2H,CH2),1.
40-1.
38(m,2H,CH2),1.
06(s,3H,CH3),0.
92(s,3H,CH3),0.
79(t,J=14.
4Hz,3H,CH3).
13CNMR(100MHz,DMSO)δ:192.
1,171.
4,147.
1,146.
8,139.
6,135.
7,130.
3,124.
6,122.
5,108.
9,108.
2,104.
5,101.
2,68.
2,34.
7,25.
6,24.
7,17.
6,13.
4.
HRMS(ESI):m/zcalcdfor:C27H26BrNaNO5,546.
0887,found:546.
0892.
2-(benzo[d][1,3]dioxol-5-yl)-1-(4-bromophenyl)-4,5,6,7-tetrahydro-6,6-dimethyl-4-oxo-1H-indol-7-ylisobutyrate4wThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,9:1,v/v)(Mp:>184-186oC).
IR(KBr,,cm-1):1738,1666,1480,1456,1232,1143,1037,836,806,724.
1HNMR(400MHz,DMSO)δ:7.
71(d,J=7.
6Hz,1H,ArH),7.
55(d,J=7.
6Hz,1H,ArH),7.
47(d,J=7.
6Hz,1H,ArH),6.
96(d,J=7.
6Hz,1H,ArH),6.
81-6.
79(m,1H,ArH),6.
73(s,1H,ArH),6.
61(s,1H,ArH),6.
59(s,1H,OCH),5.
98(s,2H,CH2),5.
67(s,1H,CH),2.
62(d,J=16.
4Hz,1H,CH2),2.
21(d,J=16.
4Hz,1H,CH2),2.
35-2.
28(m,1H,CH2),1.
07(s,3H,CH3),1.
00(t,J=14.
4Hz,3H,CH3),0.
91(s,3H,CH3),0.
88(t,J=14.
4Hz,3H,CH3).
13CNMR(100MHz,DMSO)δ:192.
1,174.
7,147.
1,146.
8,139.
5,137.
3,135.
7,124.
6,122.
5,120.
9,108.
8,104.
5,101.
2,68.
1,47.
8,33.
1,25.
7,24.
6,19.
2,18.
3.
HRMS(ESI):m/zcalcdfor:C27H26BrNNaO5,546.
0887,found:546.
0892.
Generalprocedureforthesynthesisofbis-indoles5Exampleforthesynthesisof5a:6,7-dihydro-7-(4-hydroxy-2-phenyl-1-p-tolyl-1H-indol-3-yl)-2-phenyl-1-p-tolyl-1H-indol-4(5H)-oneMicrowaveHeating:Phenylglyoxalmonohydrate(1a,2.
2mmol,0.
34g,1.
1equiv.
)wasintroducedina10-mLInitiatorTMreactionvial,3-(p-tolylamino)cyclohex-2-enone(2g,2.
0mmol,0.
40g,1.
0equiv.
)andaceticacid(2mL,excess.
)werethensuccessivelyadded.
Subsequently,thereactionvialwascappedandthenpre-stirringfor20second.
Themixturewasirradiated(Time:20min,Temperature:100oC;AbsorptionLevel:High;FixedHoldTime)untilTLC(petroleumether:acetone3:1)revealedthatconversionofthestartingmaterial2gwascompleted.
Thereactionmixturewasthencooledtoroomtemperatureandthenstirredfor30min.
ThesolidproductwascollectedbyBüchnerfiltrationandwaspurifiedbyflashcolumnchromatography(silicagel,mixturesofpetroleumether/acetone,7:1,v/v)toaffordthedesiredpureproducts5aaswhitesolid(Mp:262-263oC).
IR(KBr,,cm-1):1643,1518,1462,1289,1185,1018,953,842,747,635.
1HNMR(400MHz,DMSO)δ:7.
31-7.
28(m,3H,ArH),7.
21-7.
02(m,6H,ArH),7.
00-6.
86(m,7H,ArH),6.
81-6.
79(m,6H,ArH),6.
59(d,J=8.
0Hz,1H,ArH),6.
51(d,J=7.
6Hz,1H,ArH),6.
45-6.
39(m,1H,ArH),6.
07(d,J=7.
6Hz,1H,ArH),4.
58-4.
53(m,1H,CH),3.
02-2.
91(m,1H,CH2),2.
78-2.
74(m,1H,CH2),2.
56-2.
52(m,1H,CH2),2.
35(s,3H,CH3),2.
29(s,3H,CH3).
13CNMR(100MHz,DMSO)δ:195.
6,194.
6,189.
9,149.
7,146.
7,136.
8,134.
9,130.
8,127.
9,127.
6,126.
8,123.
3,114.
0,107.
6,106.
2,106.
0,102.
8,95.
2,64.
0,41.
1,38.
2,33.
4,30.
9,24.
2,21.
2,21.
1,6.
01.
HRMS(ESI):m/zcalcdfor:C42H33N2O2,597.
2541,found:597.
2516.
2-(4-fluorophenyl)-7-(2-(4-fluorophenyl)-4-hydroxy-1-p-tolyl-1H-indol-3-yl)-6,7-dihydro-1-p-tolyl-1H-indol-4(5H)-one5bThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,7:1,v/v)(Mp:276-278oC).
IR(KBr,,cm-1):1629,1516,1453,1285,1158,1007,837,748,632,530.
1HNMR(400MHz,DMSO)δ:7.
10-6.
96(m,5H,ArH),6.
95-6.
86(m,5H,ArH),6.
80-6.
63(m,6H,ArH),6.
56(d,J=8.
4Hz,1H,ArH),6.
50(d,J=7.
6Hz,1H,ArH),6.
41-6.
40(m,1H,ArH),6.
01(d,J=7.
6Hz,1H,ArH),4.
47-4.
42(m,1H,CH),2.
97-2.
93(m,1H,CH2),2.
74-2.
71(m,1H,CH2),2.
48-2.
43(m,1H,CH2),2.
34(s,3H,CH3),2.
27(s,3H,CH3).
HRMS(ESI):m/zcalcdfor:C42H31F2N2O2,633.
2353,found:633.
2348.
2-(4-chlorophenyl)-7-(2-(4-chlorophenyl)-4-hydroxy-1-p-tolyl-1H-indol-3-yl)-6,7-dihydro-1-p-tolyl-1H-indol-4(5H)-one5cThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,7:1,v/v)(Mp:290-291oC).
IR(KBr,,cm-1):1631,1544,1452,1387,1284,1195,1095,959,833,746,631.
1HNMR(400MHz,DMSO)δ:7.
21-7.
02(m,5H,ArH),7.
00-6.
83(m,8H,ArH),6.
75-6.
64(m,3H,ArH),6.
57(d,J=8.
4Hz,1H,ArH),6.
47(d,J=7.
6Hz,1H,ArH),6.
42(d,J=8.
0Hz,1H,ArH),6.
00(d,J=8.
0Hz,1H,ArH),4.
47-4.
43(m,1H,CH),2.
94-2.
88(m,1H,CH2),2.
73-2.
70(m,1H,CH2),2.
48-2.
44(m,1H,CH2),2.
35(s,3H,CH3),2.
28(s,3H,CH3).
HRMS(ESI):m/zcalcdfor:C42H31Cl2N2O2,665.
1762,found:665.
1764.
2-(4-bromophenyl)-7-(2-(4-bromophenyl)-4-hydroxy-1-p-tolyl-1H-indol-3-yl)-6,7-dihydro-1-p-tolyl-1H-indol-4(5H)-one5dThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,7:1,v/v)(Mp:274-276oC).
IR(KBr,,cm-1):1632,1585,1432,1288,1185,1006,989,833,772,632.
1HNMR(400MHz,DMSO)δ:7.
43-7.
41(m,2H,ArH),7.
18-7.
07(m,5H,ArH),6.
95-6.
89(m,3H,ArH),6.
84-6.
73(m,5H,ArH),6.
57(d,J=8.
0Hz,1H,ArH),6.
50(d,J=8.
0Hz,1H,ArH),6.
42(d,J=8.
0Hz,1H,ArH),6.
01(d,J=8.
0Hz,1H,ArH),4.
47-4.
43(m,1H,CH),3.
02-2.
91(m,1H,CH2),2.
73-2.
71(m,1H,CH2),2.
47-2.
41(m,1H,CH2),2.
35(s,3H,CH3),2.
28(s,3H,CH3).
HRMS(ESI):m/zcalcdfor:C42H31Br2N2O2,753.
0752,found:753.
0752.
6,7-dihydro-7-(4-hydroxy-2-(4-methoxyphenyl)-1-p-tolyl-1H-indol-3-yl)-2-(4-methoxyphenyl)-1-p-tolyl-1H-indol-4(5H)-one5eThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,7:1,v/v)(Mp:269-270oC).
IR(KBr,,cm-1):1639,1507,1458,1272,1188,1012,949,839,712,623.
1HNMR(400MHz,DMSO)δ:7.
14-6.
98(m,3H,ArH),6.
92-6.
72(m,10H,ArH),6.
66-6.
55(m,4H,ArH),6.
47(d,J=8.
0Hz,1H,ArH),6.
39(d,J=8.
0Hz,1H,ArH),6.
00(d,J=7.
6Hz,1H,ArH),4.
51-4.
47(m,1H,CH),3.
82(s,3H,OCH3),3.
69(s,3H,OCH3),2.
91-2.
81(m,1H,CH2),2.
74-2.
70(m,2H,CH2),2.
51-2.
47(m,1H,CH2),2.
33(s,3H,CH3),2.
27(s,3H,CH3).
HRMS(ESI):m/zcalcdfor:C44H37N2O4,657.
2753,found:657.
2751.
6,7-dihydro-7-(4-hydroxy-2-(4-methoxyphenyl)-1-p-tolyl-1H-indol-3-yl)-2-(4-methoxyphenyl)-1-p-tolyl-1H-indol-4(5H)-one5fThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,7:1,v/v)(Mp:233-234oC).
IR(KBr,,cm-1):1632,1515,1452,1283,1195,1008,959,832,742,630.
1HNMR(400MHz,DMSO)δ:7.
23-7.
19(m,2H,ArH),7.
15-6.
75(m,10H,ArH),6.
68-6.
56(m,4H,ArH),6.
48-6.
36(m,4H,ArH),6.
05(d,J=8.
0Hz,1H,ArH),4.
61-4.
57(m,1H,CH),3.
70(s,3H,OCH3),3.
51(s,3H,OCH3),2.
91-2.
87(m,1H,CH2),2.
77-2.
72(m,2H,CH2),2.
52-2.
49(m,1H,CH2),2.
33(s,3H,CH3),2.
27(s,3H,CH3).
HRMS(ESI):m/zcalcdfor:C44H37N2O4,657.
2753,found:657.
2795.
1-(4-chlorophenyl)-7-(1-(4-chlorophenyl)-2-(4-fluorophenyl)-4-hydroxy-1H-indol-3-yl)-2-(4-fluorophenyl)-6,7-dihydro-1H-indol-4(5H)-one5gThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,7:1,v/v)(Mp:288-289oC).
IR(KBr,,cm-1):1627,1493,1461,1225,1196,1159,1090,1015,816,741,523.
1HNMR(400MHz,DMSO)δ:7.
41-7.
31(m,2H,ArH),7.
24-7.
16(m,2H,ArH),7.
07-6.
91(m,7H,ArH),6.
90-6.
66(m,5H,ArH),6.
56(d,J=8.
0Hz,1H,ArH),6.
55-6.
50(m,2H,ArH),6.
09-6.
06(m,1H,ArH),4.
50-4.
47(m,1H,CH),3.
07-3.
01(m,1H,CH2),2.
77-2.
75(m,1H,CH2),2.
52-2.
49(m,1H,CH2).
HRMS(ESI):m/zcalcdfor:C40H25Cl2F2N2O2,673.
1260,found:673.
1214.
1-(4-chlorophenyl)-7-(1-(4-chlorophenyl)-4-hydroxy-2-p-tolyl-1H-indol-3-yl)-6,7-dihydro-2-p-tolyl-1H-indol-4(5H)-one5hThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,7:1,v/v)(Mp:291-293oC).
IR(KBr,,cm-1):1639,1493,1458,1287,1192,1090,842,743,620.
1HNMR(400MHz,DMSO)δ:7.
33-7.
29(m,2H,ArH),7.
25-7.
15(m,3H,ArH),7.
07-7.
05(m,2H,ArH),7.
00-6.
75(m,9H,ArH),6.
56(d,J=8.
4Hz,1H,ArH),6.
46(d,J=8.
0Hz,1H,ArH),6.
50-6.
44(m,1H,ArH),6.
09(d,J=8.
0Hz,1H,ArH),4.
57-4.
53(m,1H,CH),3.
02-2.
97(m,1H,CH2),2.
77-2.
75(m,1H,CH2),2.
57-2.
53(m,1H,CH2),2.
37(s,3H,CH3),2.
21(s,3H,CH3).
HRMS(ESI):m/zcalcdfor:C42H31Cl2N2O2,665.
1762,found:665.
1751.
2-(benzo[d][1,3]dioxol-5-yl)-7-(2-(benzo[d][1,3]dioxol-6-yl)-1-(4-chlorophenyl)-4-hydroxy-1H-indol-3-yl)-1-(4-chlorophenyl)-6,7-dihydro-1H-indol-4(5H)-one5iThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,7:1,v/v)(Mp:280-284oC).
IR(KBr,,cm-1):1633,1518,1442,1253,1152,1019,979,846,746,638.
1HNMR(400MHz,DMSO)δ:7.
41-7.
32(m,2H,ArH),7.
07-7.
03(m,2H,ArH),6.
93-6.
91(m,1H,ArH),6.
85-6.
76(m,5H,ArH),6.
54-6.
49(m,5H,ArH),6.
40-6.
38(m,2H,ArH),6.
13(d,J=8.
8Hz,1H,ArH),6.
02(s,2H,CH2),5.
85(s,2H,CH2),4.
55-4.
51(m,1H,CH),3.
06-3.
01(m,1H,CH2),2.
78-2.
77(m,2H,CH2),2.
52-2.
48(m,1H,CH2).
HRMS(ESI):m/zcalcdfor:C42H27Cl2N2O6,725.
1245,found:725.
1246.
1-(4-fluorophenyl)-7-(1-(4-fluorophenyl)-4-hydroxy-2-phenyl-1H-indol-3-yl)-6,7-dihydro-2-phenyl-1H-indol-4(5H)-one5jThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,7:1,v/v)(Mp:267-270oC).
IR(KBr,,cm-1):1636,1514,1457,1273,1195,1029,978,812,748,633.
1HNMR(400MHz,DMSO)δ:7.
33-7.
30(m,3H,ArH),7.
23-7.
19(m,3H,ArH),7.
09-6.
95(m,5H,ArH),6.
93-6.
75(m,7H,ArH),6.
53(d,J=8.
0Hz,1H,ArH),6.
46(d,J=8.
0Hz,1H,ArH),6.
25-6.
13(m,2H,ArH),4.
59-4.
55(m,1H,CH),2.
99-2.
96(m,1H,CH2),2.
77-2.
74(m,2H,CH2),2.
57-2.
55(m,1H,CH2).
HRMS(ESI):m/zcalcdfor:C40H27F2N2O2,605.
2040,found:605.
2045.
2-(benzo[d][1,3]dioxol-5-yl)-7-(2-(benzo[d][1,3]dioxol-6-yl)-1-(4-fluorophenyl)-4-hydroxy-1H-indol-3-yl)-1-(4-fluorophenyl)-6,7-dihydro-1H-indol-4(5H)-one5kThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,9:1,v/v)(Mp:184-186oC).
IR(KBr,,cm-1):1636,1511,1452,1243,1195,1007,957,852,792,638.
1HNMR(400MHz,DMSO)δ:7.
06-6.
89(m,5H,ArH),6.
85-6.
76(m,4H,ArH),6.
55-6.
39(m,6H,ArH),6.
25-6.
6.
18(m,3H,ArH),6.
01(s,2H,CH2),5.
84(s,2H,CH2),4.
55-4.
51(m,1H,CH),3.
01-2.
92(m,1H,CH2),2.
76-2.
75(m,2H,CH2),2.
50-2.
46(m,1H,CH2).
HRMS(ESI):m/zcalcdfor:C42H27F2N2O6,693.
1836,found:693.
1835.
6,7-dihydro-7-(4-hydroxy-1-(4-methoxyphenyl)-2-phenyl-1H-indol-3-yl)-1-(4-methoxyphenyl)-2-phenyl-1H-indol-4(5H)-one5lThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,7:1,v/v)(Mp:267-269oC).
IR(KBr,,cm-1):1637,1512,1472,1288,1196,1005,969,839,743,631.
1HNMR(400MHz,DMSO)δ:7.
29-7.
26(m,3H,ArH),7.
19-7.
00(m,5H,ArH),6.
96-6.
76(m,7H,ArH),6.
65-6.
63(m,3H,ArH),6.
52(d,J=8.
0Hz,1H,ArH),6.
45(d,J=7.
6Hz,1H,ArH),6.
10-6.
02(m,2H,ArH),4.
56-4.
51(m,1H,CH),3.
79(s,3H,OCH3),3.
72(s,3H,OCH3),2.
94-2.
91(m,1H,CH2),2.
80-2.
67(m,2H,CH2),2.
53-2.
51(m,1H,CH2).
HRMS(ESI):m/zcalcdfor:C42H33N2O4,629.
2440,found:629.
2480.
R.
China;and2DepartmentofChemistryandBiochemistry,TexasTechUniversity,Lubbock,TX79409-1061ExperimentalGeneralinformationMicrowaveirradiationwascarriedoutwithInitiator2.
5MicrowaveSynthesizersfromBiotage,Uppsala,Sweden.
Meltingpointsweredeterminedinopencapillariesandwereuncorrected.
IRspectraweretakenonaFT-IR-Tensor27spectrometerinKBrpelletsandreportedincm-1.
1HNMRspectraweremeasuredonaBrukerDPX400MHzspectrometerinDMSO-d6withchemicalshift(δ)giveninppmrelativetoTMSasinternalstandard[(s=singlet,d=doublet,t=triplet,brs=broadsinglet,m=multiplet),couplingconstant(Hz)].
HRMS(ESI)wasdeterminedbyusingmicroTOF-QⅡHRMS/MSinstrument(BRUKER).
X-RaycrystallographicanalysiswasperformedwithaSiemensSMARTCCDandaSiemensP4diffractometer.
Fig1,X-rayStructureofindoles4aFig2,X-rayStructureofbis-indoles5aCrystaldatafor4a:C25H25NO3,Mr=387.
46,Monoclinic,a=8.
6760(8),b=12.
8793(13),c=9.
4794(11),U=1045.
73(19)3,T=298(2)K,spacegroupP2(1),Z=2,5349reflectionsmeasured,1936unique(Rint=0.
0428)whichwereusedinallcalculation.
ThefinalwR(F2)was0.
0638(alldata)Crystaldatafor5a:C42H34N2O2,Mr=598.
71,Triclinic,a=10.
0878(13),b=11.
1881(13),c=15.
2089(16),U=1594.
8(3)3,T=298(2)K,spacegroupP-1,Z=2,8283reflectionsmeasured,5520unique(Rint=0.
1165)whichwereusedinallcalculation.
ThefinalwR(F2)was0.
2184(alldata)Generalprocedureforthesynthesisofindoles4Exampleforthesynthesisof4a:4,5,6,7-tetrahydro-6,6-dimethyl-4-oxo-1,2-diphenyl-1H-indol-7-ylacetateMicrowaveHeating:phenylglyoxalmonohydrate(1a,1.
1mmol,0.
17g,1.
1equiv.
)wasintroducedina10-mLInitiatorTMreactionvial,3-(p-tolylamino)-5,5-dimethylcyclohex-2-enone(2a,1.
0mmol,0.
23g,1.
0equiv.
)andaceticacid(3a,2mL,excess.
)werethensuccessivelyadded.
Subsequently,thereactionvialwascappedandthenpre-stiringfor20second.
Themixturewasirradiated(Time:15min,Temperature:120oC;AbsorptionLevel:High;FixedHoldTime)untilTLC(petroleumether:acetone4:1)revealedthatconversionofthestartingmaterial2awascomplete.
Thereactionmixturewasthencooledtoroomtemperatureandthendilutedwithcoldwater(20ml).
ThesolidproductwascollectedbyBüchnerfiltrationandwaspurifiedbyflashcolumnchromatography(silicagel,mixturesofpetroleumether/acetone,9:1,v/v)toaffordthedesiredpureindoles4aaswhitesolid(Mp:124-126oC).
IR(KBr,,cm-1):1739,1667,1495,1465,1371,1229,1051,1015,968,766.
1HNMR(400MHz,DMSO)δ:7.
50-7.
38(m,4H,ArH),7.
23-7.
19(m,3H,ArH),7.
15-7.
12(m,2H,ArH),6.
70(s,1H,CH),5.
58(s,1H,OCH),2.
64(d,J=15.
6Hz,1H,CH2),2.
20(d,J=16.
4Hz,1H,CH2),1.
84(s,3H,CH3),1.
06(s,3H,CH3),0.
93(s,3H,CH3).
13CNMR(100MHz,DMSO)δ:192.
1,168.
9,140.
0,137.
5,136.
4,131.
0,129.
1,128.
2,128.
1,127.
4,120.
7,104.
6,68.
4,47.
7,30.
7,25.
6,24.
8,20.
2.
HRMS(ESI):m/zcalcdfor:C24H24NO3,374.
1751,found:374.
1757.
Scopeofmulticomponentdominoreaction1-(4-Fluorophenyl)-4,5,6,7-tetrahydro-6,6-dimethyl-4-oxo-2-phenyl-1H-indol-7-ylacetate4bThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,9:1,v/v)(Mp:190-192oC).
IR(KBr,,cm-1):1744,1668,1509,1464,1371,1227,1050,1016,968,855.
1HNMR(400MHz,DMSO)δ:7.
52(s,1H,ArH),7.
53(d,J=8.
0Hz,1H,ArH),7.
24-7.
21(m,4H,ArH),7.
16-7.
14(m,3H,ArH),6.
69(s,1H,CH),5.
56(s,1H,OCH),2.
65(d,J=16.
4Hz,1H,CH2),2.
20(d,J=16.
4Hz,1H,CH2),1.
88(s,3H,CH3),1.
07(s,3H,CH3),0.
94(s,3H,CH3).
13CNMR(100MHz,DMSO)δ:192.
0,169.
0,161.
7(1JCF=244.
5Hz),140.
1,137.
6,132.
6(4JCF=2.
7Hz),130.
8,130.
5(3JCF=9.
4Hz),128.
3,128.
2,127.
5,120.
7,116.
1(2JCF=24.
1Hz),112.
6,104.
5,68.
2,47.
6,25.
5,24.
7,20.
1.
HRMS(ESI):m/zcalcdfor:C24H22FNNaO3,414.
1476,found:414.
1481.
1-(4-Bromophenyl)-4,5,6,7-tetrahydro-6,6-dimethyl-4-oxo-2-phenyl-1H-indol-7-ylacetate4cThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,9:1,v/v)(Mp:158-160oC).
IR(KBr,,cm-1):1739,1664,1492,1457,1225,1048,1017,900,846.
1HNMR(400MHz,DMSO)δ:7.
69(s,1H,ArH),7.
57(d,J=8.
0Hz,1H,ArH),7.
39(d,J=7.
2Hz,1H,ArH),7.
27-7.
22(m,3H,ArH),7.
16-7.
14(m,2H,ArH),7.
07(d,J=5.
6Hz,1H,ArH),6.
69(s,1H,CH),5.
57(s,1H,OCH),2.
64(d,J=16.
4Hz,1H,CH2),2.
21(d,J=16.
4Hz,1H,CH2),1.
88(s,3H,CH3),1.
06(s,3H,CH3),0.
94(s,3H,CH3).
13CNMR(100MHz,DMSO)δ:192.
1,169.
1,140.
0,137.
5,135.
7,130.
8,130.
4,128.
4,128.
3,127.
6,122.
2,120.
9,104.
8,68.
4,47.
7,25.
5,24.
8,20.
2.
HRMS(ESI):m/zcalcdfor:C24H22BrNNaO3,474.
0676,found:474.
0652.
4,5,6,7-tetrahydro-6,6-dimethyl-4-oxo-2-phenyl-1-p-tolyl-1H-indol-7-ylacetate4dThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,9:1,v/v)(Mp:>198-200oC).
IR(KBr,,cm-1):1737,1661,1515,1458,1228,1049,1020,966,831,772.
1HNMR(400MHz,DMSO)δ:7.
27-7.
24(m,1H,ArH),7.
22-7.
18(m,5H,ArH),7.
15-7.
13(m,2H,ArH),7.
01(d,J=7.
6Hz,1H,ArH),6.
67(s,1H,CH),5.
54(s,1H,OCH),2.
64(d,J=16.
8Hz,1H,CH2),2.
33(s,3H,CH3),2.
22(d,J=16.
4Hz,1H,CH2),1.
89(s,3H,CH3),1.
04(s,3H,CH3),0.
93(s,3H,CH3).
13CNMR(100MHz,DMSO)δ:192.
0,169.
0,140.
1,138.
4,137.
4,133.
7,131.
0,128.
2,128.
1,127.
8,127.
3,120.
6,104.
5,68.
4,47.
6,25.
4,24.
8,20.
6,20.
2.
HRMS(ESI):m/zcalcdfor:C25H25NNaO3,410.
1727,found:410.
1736.
4,5,6,7-Tetrahydro-6,6-dimethyl-4-oxo-1,2-diphenyl-1H-indol-7-ylpropionate4eThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,9:1,v/v)(Mp:123-125oC).
IR(KBr,,cm-1):1741,1666,1498,1459,1165,1078,809,763,701.
1HNMR(400MHz,DMSO)δ:7.
48-7.
36(m,3H,ArH),7.
36(d,J=14Hz,1H,ArH),7.
21-7.
12(m,5H,ArH),7.
07(d,J=14Hz,1H,ArH),6.
70(s,1H,CH),5.
64(s,1H,OCH),2.
83(d,J=16.
4Hz,1H,CH2),2.
23-2.
03(m,2H,CH2),2.
18(d,J=16.
4Hz,1H,CH2),1.
07(s,3H,CH3),0.
92(s,3H,CH3),0.
87(t,J=14.
8Hz,3H,CH3).
13CNMR(100MHz,DMSO)δ:192.
0,172.
1,140.
0,137.
4,136.
3,131.
0,128.
9,128.
2,128.
1,127.
3,120.
7,104.
5,68.
2,47.
7,26.
3,25.
6,24.
7,8.
8.
HRMS(ESI):m/zcalcdfor:C25H26NO3,388.
1908,found:388.
1912.
1-(4-Fluorophenyl)-4,5,6,7-tetrahydro-6,6-dimethyl-4-oxo-2-phenyl-1H-indol-7-ylpropionate4fThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,9:1,v/v)(Mp:130-132oC).
IR(KBr,,cm-1):1744,1672,1509,1463,1368,1157,1050,917,857,764.
1HNMR(400MHz,DMSO)δ:7.
55(s,1H,ArH),7.
34(d,J=8.
4Hz,1H,ArH),7.
27-7.
19(m,4H,ArH),7.
16-7.
14(m,3H,ArH),6.
69(s,1H,CH),5.
63(s,1H,OCH),2.
64(d,J=16.
4Hz,1H,CH2),2.
27-2.
05(m,2H,CH2),2.
17(d,J=16.
4Hz,1H,CH2),1.
08(s,3H,CH3),0.
93(s,3H,CH3),0.
88(t,J=14.
8Hz,3H,CH3).
13CNMR(100MHz,DMSO)δ:192.
1,172.
3,159.
4(1JCF=228.
6Hz),140.
2,137.
7,132.
7(4JCF=2.
9Hz),130.
9,130.
5(3JCF=8.
3Hz),128.
3,128.
2,127.
5,120.
8,116.
2(2JCF=22.
0Hz),104.
6,68.
1,47.
8,38.
5,26.
4,25.
6,24.
7,8.
9.
HRMS(ESI):m/zcalcdfor:C25H24FNNaO3,428.
1633,found:428.
1640.
1-(4-chlorophenyl)-4,5,6,7-tetrahydro-6,6-dimethyl-4-oxo-2-phenyl-1H-indol-7-ylpropionate4gThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,9:1,v/v)(Mp:138-140oCoC).
IR(KBr,,cm-1):1746,1664,1496,1464,1200,1055,996,767,699.
1HNMR(400MHz,DMSO)δ:7.
59-7.
53(m,2H,ArH),7.
41(d,J=8.
0Hz,1H,ArH),7.
28-7.
22(m,3H,ArH),7.
21-7.
14(m,3H,ArH),7.
08(d,J=8.
4Hz,1H,ArH),6.
70(s,1H,CH),5.
66(s,1H,OCH),2.
63(d,J=16.
4Hz,1H,CH2),2.
25-2.
04(m,2H,CH2),2.
23(d,J=16.
4Hz,1H,CH2),1.
07(s,3H,CH3),0.
93(s,3H,CH3),0.
89(t,J=7.
2Hz,3H,CH3).
13CNMR(100MHz,DMSO)δ:192.
1,172.
3,137.
6,135.
3,133.
6,130.
8,128.
4,128.
3,127.
6,124.
1,104.
8,68.
2,47.
8,30.
7,26.
4,25.
7,24.
6,8.
8.
HRMS(ESI):m/zcalcdfor:C25H24ClNNaO3,444.
1337,found:444.
1345.
1-(4-bromophenyl)-4,5,6,7-tetrahydro-6,6-dimethyl-4-oxo-2-phenyl-1H-indol-7-ylpropionate4hThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,9:1,v/v)(Mp:122-123oC).
IR(KBr,,cm-1):1747,1674,1489,1461,1200,1151,1050,1018,763.
1HNMR(400MHz,DMSO)δ:7.
70(d,J=8.
0Hz,1H,ArH),7.
55(d,J=8.
0Hz,1H,ArH),7.
44(d,J=8.
0Hz,1H,ArH),7.
28-7.
23(m,3H,ArH),7.
16-7.
14(m,2H,ArH),7.
01(d,J=7.
6Hz,1H,ArH),6.
69(s,1H,CH),5.
66(s,1H,OCH),2.
62(d,J=16.
4Hz,1H,CH2),2.
27-2.
04(m,2H,CH2),2.
19(d,J=16.
8Hz,1H,CH2),1.
07(s,3H,CH3),0.
93(s,3H,CH3),0.
88(t,J=14.
8Hz,3H,CH3).
13CNMR(100MHz,DMSO)δ:192.
3,172.
4,140.
1,137.
5,135.
7,130.
7,128.
4,128.
3,127.
6,122.
1,120.
9,104.
8,68.
2,47.
9,30.
7,26.
4,25.
6,24.
6,8.
8.
HRMS(ESI):m/zcalcdfor:C25H24BrNNaO3,488.
0832,found:488.
0850.
4,5,6,7-tetrahydro-6,6-dimethyl-4-oxo-2-phenyl-1-p-tolyl-1H-indol-7-ylpropionate4iThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,9:1,v/v)(Mp:127-128oC).
IR(KBr,,cm-1):1739,1671,1516,1457,1164,1076,1048,812,765,700.
1HNMR(400MHz,DMSO)δ:7.
26-7.
24(m,2H,ArH),7.
22-7.
19(m,3H,ArH),7.
15-7.
13(m,3H,ArH),6.
95(d,J=6.
4Hz,1H,ArH),6.
67(s,1H,CH),5.
62(s,1H,OCH),2.
62(d,J=16.
4Hz,1H,CH2),2.
33(s,3H,CH3),2.
24-2.
05(m,2H,CH2),2.
21(d,J=16.
4Hz,1H,CH2),1.
05(s,3H,CH3),0.
92(s,3H,CH3),0.
89(t,J=7.
6Hz,3H,CH3).
13CNMR(100MHz,DMSO)δ:192.
0,172.
2,140.
1,138.
3,137.
4,133.
8,131.
0,128.
2,128.
1,127.
8,127.
7,127.
3,120.
6,104.
5,68.
3,47.
7,26.
4,25.
5,24.
8,20.
6,8.
8.
HRMS(ESI):m/zcalcdfor:C26H27NNaO3,424.
1884,found:424.
1889.
4,5,6,7-tetrahydro-1-(4-methoxyphenyl)-6,6-dimethyl-4-oxo-2-phenyl-1H-indol-7-ylpropionate4jThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,9:1,v/v)(Mp:186-187oC).
IR(KBr,,cm-1):1743,1668,1512,1466,1252,1052,1030,917,850,761,.
1HNMR(400MHz,DMSO)δ:7.
33(d,J=8.
0Hz,1H,ArH),7.
23-7.
15(m,5H,ArH),7.
01-7.
00(m,2H,ArH),6.
88(d,J=8.
0Hz,1H,ArH),6.
67(s,1H,CH),5.
61(s,1H,OCH),2.
63(d,J=16.
4Hz,1H,CH2),2.
28-2.
09(m,2H,CH2),2.
19(d,J=16.
4Hz,1H,CH2),1.
06(s,3H,CH3),0.
92(s,3H,CH3),0.
89(t,J=7.
2Hz,3H,CH3).
13CNMR(100MHz,DMSO)δ:192.
0,172.
2,159.
1,140.
3,137.
6,131.
1,129.
3,129.
2,128.
9,128.
2,128.
1,127.
3,120.
4,114.
4,104.
3,68.
2,55.
3,47.
7,26.
4,25.
6,24.
7,8.
8.
HRMS(ESI):m/zcalcdfor:C26H27NNaO4,440.
1833,found:440.
1831.
1-(4-chlorophenyl)-4,5,6,7-tetrahydro-6,6-dimethyl-4-oxo-2-phenyl-1H-indol-7-ylbutyrate4kThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,9:1,v/v)(Mp:147-149oC).
IR(KBr,,cm-1):1744,1674,1493,1463,1152,1049,853,762,727,698.
1HNMR(400MHz,DMSO)δ:7.
39(d,J=8.
0Hz,1H,ArH),7.
27-7.
21(m,3H,ArH),7.
15-7.
13(m,2H,ArH),7.
06(d,J=8.
0Hz,1H,ArH),6.
69(s,1H,CH),5.
67(s,1H,OCH),2.
62(d,J=16.
4Hz,1H,CH2),2.
24-1.
98(m,2H,CH2),2.
03(d,J=16.
4Hz,1H,CH2),1.
41-1.
35(m,2H,CH2),1.
08(s,3H,CH3),0.
93(s,3H,CH3),0.
89(t,J=14.
8Hz,3H,CH3).
13CNMR(100MHz,DMSO)δ:192.
1,171.
4,140.
0,137.
5,135.
3,133.
6,130.
8,128.
4,128.
3,127.
6,121.
0,104.
8,68.
2,47.
8,34.
7,30.
7,25.
6,24.
7,17.
6,13.
4.
HRMS(ESI):m/zcalcdfor:C26H27ClNO3,436.
1674,found:436.
1678.
1-(4-Bromophenyl)-4,5,6,7-tetrahydro-6,6-dimethyl-4-oxo-2-phenyl-1H-indol-7-ylbutyrate4lThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,9:1,v/v)(Mp:145-146oC).
IR(KBr,,cm-1):1744,1673,1489,1462,1150,1075,852,763,719,698.
1HNMR(400MHz,DMSO)δ:7.
71(d,J=7.
6Hz,1H,ArH),7.
53(d,J=7.
6Hz,1H,ArH),7.
46(d,J=7.
6Hz,1H,ArH),7.
28-7.
22(m,3H,ArH),7.
15-7.
13(m,2H,ArH),6.
99(d,J=7.
2Hz,1H,ArH),6.
69(s,1H,CH),5.
68(s,1H,OCH),2.
62(d,J=16.
4Hz,1H,CH2),2.
25-2.
15(m,2H,CH2),2.
20(d,J=16.
4Hz,1H,CH2),1.
43-1.
34(m,2H,CH2),1.
08(s,3H,CH3),0.
93(s,3H,CH3),0.
79(t,J=14.
8Hz,3H,CH3).
13CNMR(100MHz,DMSO)δ:192.
1,171.
4,140.
0,137.
5,135.
8,130.
8,130.
3,128.
4,127.
6,122.
1,121.
0,104.
9,68.
2,47.
8,34.
7,30.
7,25.
6,24.
7,17.
6,13.
4.
HRMS(ESI):m/zcalcdfor:C26H27BrNO3,480.
1169,found:480.
1167.
4,5,6,7-tetrahydro-6,6-dimethyl-4-oxo-2-phenyl-1-p-tolyl-1H-indol-7-ylbutyrate4mThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,9:1,v/v)(Mp:136-137oC).
IR(KBr,,cm-1):1739,1667,1516,1458,1410,1162,969,765,698.
1HNMR(400MHz,DMSO)δ:7.
27-7.
24(m,2H,ArH),7.
22-7.
19(m,3H,ArH),7.
18-7.
12(m,3H,ArH),6.
94(d,J=7.
6Hz,1H,ArH),6.
68(s,1H,CH),5.
63(s,1H,OCH),2.
63(d,J=16.
4Hz,1H,CH2),2.
32(s,3H,CH3),2.
22-2.
17(m,2H,CH2),2.
04(d,J=16.
0Hz,1H,CH2),1.
40-1.
38(m,2H,CH2),1.
05(s,3H,CH3),0.
92(s,3H,CH3),0.
80(t,J=14.
8Hz,3H,CH3).
13CNMR(100MHz,DMSO)δ:192.
1,171.
4,140.
1,137.
5,133.
8,131.
1,128.
3,127.
8,120.
7,104.
6,68.
3,47.
7,34.
8,30.
7,25.
7,20.
7,17.
6,13.
4.
HRMS(ESI):m/zcalcdfor:C27H29NNaO3,438.
2040,found:438.
2041.
4,5,6,7-tetrahydro-1-(4-methoxyphenyl)-6,6-dimethyl-4-oxo-2-phenyl-1H-indol-7-ylbutyrate4nThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasapaleyellowsolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,9:1,v/v)(Mp:127-128oC).
IR(KBr,,cm-1):1740,1669,1513,1465,1251,1156,850,760,697.
1HNMR(400MHz,DMSO)δ:7.
33(d,J=8.
0Hz,1H,ArH),7.
25-7.
23(m,5H,ArH),7.
03-6.
98(m,2H,ArH),6.
87(d,J=8.
0Hz,1H,ArH),6.
67(s,1H,CH),5.
62(s,1H,OCH),3.
76(s,3H,OCH3),2.
63(d,J=16.
8Hz,1H,CH2),2.
24-2.
03(m,2H,CH2),2.
19(d,J=16.
8Hz,1H,CH2),1.
44-1.
35(m,2H,CH2),1.
06(s,3H,CH3),0.
92(s,3H,CH3),0.
80(t,J=14.
4Hz,3H,CH3).
13CNMR(100MHz,DMSO)δ:192.
1,171.
4,159.
2,140.
3,137.
6,131.
1,129.
0,128.
3,127.
4,120.
5,114.
5,104.
4,68.
2,55.
4,34.
8,30.
7,25.
6,24.
9,17.
7,13.
4.
HRMS(ESI):m/zcalcdfor:C27H30NO4,432.
2170,found:432.
2154.
1-(4-fluorophenyl)-4,5,6,7-tetrahydro-6,6-dimethyl-4-oxo-2-phenyl-1H-indol-7-ylisobutyrate4oThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,9:1,v/v)(Mp:117-119oC).
IR(KBr,,cm-1):1735,1669,1513,1459,1150,1050,849,763,698.
1HNMR(400MHz,DMSO)δ:7.
59(s,1H,ArH),7.
37(d,J=8.
8Hz,1H,ArH),7.
27-7.
23(m,3H,ArH),7.
16-7.
14(m,3H,ArH),7.
06(s,1H,ArH),6.
70(s,1H,CH),5.
66(s,1H,OCH),2.
66(d,J=16.
4Hz,1H,CH2),2.
40-2.
33(m,1H,CH),2.
21(d,J=16.
4Hz,1H,CH2),1.
09(s,3H,CH3),1.
00(t,J=6.
8Hz,3H,CH3),0.
89(t,J=6.
8Hz,3H,CH3),0.
92(s,3H,CH3).
13CNMR(100MHz,DMSO)δ:192.
1,174.
6,161.
7(1JCF=244.
9Hz),140.
1,137.
6,132.
7(4JCF=2.
8Hz),130.
8,130.
4(3JCF=8.
0Hz),128.
3,127.
5,120.
8,116.
5(2JCF=22.
2Hz),112.
7,104.
7,68.
0,47.
7,33.
1,25.
6,24.
7,19.
1.
18.
4.
HRMS(ESI):m/zcalcdfor:C26H26FNNaO3,442.
1789,found:442.
1799.
1-(4-chlorophenyl)-4,5,6,7-tetrahydro-6,6-dimethyl-4-oxo-2-phenyl-1H-indol-7-ylisobutyrate4pThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,9:1,v/v)(Mp:165-166oC).
IR(KBr,,cm-1):1736,1673,1496,1455,1145,1093,852,769,702.
1HNMR(400MHz,DMSO)δ:7.
57(s,2H,ArH),7.
40(d,J=8.
0Hz,1H,ArH),7.
26-7.
14(m,5H,ArH),7.
02(d,J=8.
4Hz,1H,ArH),6.
70(s,1H,CH),5.
70(s,1H,OCH),2.
65(d,J=16.
4Hz,1H,CH2),2.
35-2.
30(m,1H,CH),2.
23(d,J=16.
4Hz,1H,CH2),1.
08(s,3H,CH3),1.
01(t,J=7.
2Hz,3H,CH3)0.
93(s,3H,CH3),0.
88(t,J=6.
8Hz,3H,CH3).
13CNMR(100MHz,DMSO)δ:206.
5,192.
1,174.
7,139.
9,137.
5,135.
7,130.
8,128.
3,127.
6,122.
0,121.
0,104.
9,68.
1,47.
8,33.
1,30.
7,25.
7,24.
6,19.
1.
18.
3.
HRMS(ESI):m/zcalcdfor:C26H27ClNO3,436.
1674,found:436.
1677.
1-(4-bromophenyl)-4,5,6,7-tetrahydro-6,6-dimethyl-4-oxo-2-phenyl-1H-indol-7-ylisobutyrate4qThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,9:1,v/v)(Mp:176-177oC).
IR(KBr,,cm-1):1736,1672,1494,1456,1411,1145,1048,850,767,700.
1HNMR(400MHz,DMSO)δ:7.
71(d,J=8.
4Hz,1H,ArH),7.
53-7.
48(m,2H,ArH),7.
26-7.
22(m,3H,ArH),7.
16-7.
14(m,2H,ArH),6.
95(d,J=8.
4Hz,1H,ArH),6.
70(s,1H,CH),5.
70(s,1H,OCH),2.
64(d,J=16.
4Hz,1H,CH2),2.
34-2.
30(m,H,CH),2.
23(d,J=16.
4Hz,1H,CH2),1.
08(s,3H,CH3),1.
00(t,J=7.
2Hz,3H,CH3),0.
88(t,J=6.
8Hz,3H,CH3)0.
92(s,3H,CH3).
13CNMR(100MHz,DMSO)δ:206.
5,192.
1,174.
7,139.
9,137.
5,135.
7,130.
8,128.
3,127.
6,122.
0,121.
0,104.
9,68.
1,47.
8,33.
1,30.
7,25.
7,24.
6,19.
1.
18.
3.
HRMS(ESI):m/zcalcdfor:C26H26BrNNaO3,502.
0989,found:502.
1005.
4,5,6,7-tetrahydro-6,6-dimethyl-4-oxo-2-phenyl-1-p-tolyl-1H-indol-7-ylisobutyrate4rThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,9:1,v/v)(Mp:162-164oC).
IR(KBr,,cm-1):1734,1670,1516,1456,1217,1145,1049,846,767,701.
1HNMR(400MHz,DMSO)δ:7.
29(m,2H,ArH),7.
24-7.
19(m,3H,ArH),7.
15-7.
13(m,3H,ArH),6.
90(d,J=6.
0Hz,1H,ArH),6.
70(s,1H,CH),5.
70(s,1H,OCH),2.
64(d,J=16.
4Hz,1H,CH2),2.
38-2.
34(m,1H,CH),2.
32(s,3H,CH3),2.
21(d,J=16.
4Hz,1H,CH2),1.
06(s,3H,CH3),1.
01(t,J=7.
2Hz,3H,CH3)0.
91(s,3H,CH3),0.
90(t,J=6.
8Hz,3H,CH3).
13CNMR(100MHz,DMSO)δ:206.
5,192.
1,174.
6,140.
0,137.
5,135.
3,133.
5,130.
8,128.
3,127.
6,121.
0,104.
9,68.
1,56.
3,47.
8,33.
1,30.
7,25.
7,24.
6,19.
1,18.
3.
HRMS(ESI):m/zcalcdfor:C27H30NO3,416.
2221,found:416.
2221.
4,5,6,7-tetrahydro-1-(4-methoxyphenyl)-6,6-dimethyl-4-oxo-2-phenyl-1H-indol-7-ylisobutyrate4sThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,9:1,v/v)(Mp:181-182oC).
IR(KBr,,cm-1):1734,1667,1514,1460,1250,1147,1028,834,768,700.
1HNMR(400MHz,DMSO)δ:7.
36(d,J=8.
4Hz,1H,ArH),7.
23-7.
21(m,3H,ArH),7.
16-7.
03(m,2H,ArH),7.
02(d,J=8.
0Hz,1H,ArH),6.
94(d,J=8.
0Hz,1H,ArH),6.
86(d,J=8.
8Hz,1H,ArH),6.
67(s,1H,CH),5.
63(s,1H,OCH),3.
76(s,3H,OCH3),2.
65(d,J=16.
4Hz,1H,CH2),2.
41-2.
34(m,2H,CH2),2.
19(d,J=16.
4Hz,1H,CH2),1.
06(s,3H,CH3),1.
02(t,J=6.
8Hz,3H,CH3),0.
91(t,J=6.
8Hz,3H,CH3)0.
92(s,3H,CH3).
13CNMR(100MHz,DMSO)δ:206.
5,174.
6,162.
4,159.
2,147.
6,141.
7,137.
6,128.
3,128.
2,127.
3,120.
6,104.
4,68.
1,55.
4,33.
1,30.
7,25.
6,24.
7,19.
2,18.
3.
HRMS(ESI):m/zcalcdfor:C27H30NO4,432.
2170,found:432.
2172.
2-(benzo[d][1,3]dioxol-5-yl)-1-(4-bromophenyl)-4,5,6,7-tetrahydro-6,6-dimethyl-4-oxo-1H-indol-7-ylacetate4tThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,9:1,v/v)(Mp:159-161oC).
IR(KBr,,cm-1):1737,1678,1494,1474,1221,1036,1016,803,728.
1HNMR(400MHz,DMSO)δ:7.
70(d,J=8.
0Hz,1H,ArH),7.
59(d,J=8.
0Hz,1H,ArH),7.
38(d,J=7.
6Hz,1H,ArH),7.
08(d,J=8.
0Hz,1H,ArH),6.
82-6.
75(m,1H,ArH),6.
72(s,1H,ArH),6.
61(s,1H,ArH),6.
59(s,1H,OCH),5.
98(s,2H,CH2),5.
54(s,1H,CH),2.
63(d,J=16.
4Hz,1H,CH2),2.
19(d,J=16.
4Hz,1H,CH2),1.
88(s,3H,CH3),1.
05(s,3H,CH3),0.
93(s,3H,CH3).
13CNMR(100MHz,DMSO)δ:192.
1,169.
1,147.
1,137.
3,135.
7,132.
2,130.
4,122.
5,119.
1,108.
8,104.
4,101.
2,25.
5,21.
0,20.
2.
HRMS(ESI):m/zcalcdfor:C25H23BrNO5,496.
0755,found:496.
0730.
2-(benzo[d][1,3]dioxol-5-yl)-1-(4-bromophenyl)-4,5,6,7-tetrahydro-6,6-dimethyl-4-oxo-1H-indol-7-ylpropionate4uThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,9:1,v/v)(Mp:162-164oC).
IR(KBr,,cm-1):1735,1679,1494,1476,1232,1201,1037,873,803,728.
1HNMR(400MHz,DMSO)δ:7.
71(d,J=8.
0Hz,1H,ArH),7.
57(d,J=8.
0Hz,1H,ArH),7.
43(d,J=8.
0Hz,1H,ArH),7.
02(d,J=8.
0Hz,1H,ArH),6.
81-6.
79(m,1H,ArH),6.
73(s,1H,ArH),6.
61(s,1H,ArH),6.
59(s,1H,OCH),5.
98(s,2H,CH2),5.
63(s,1H,CH),2.
60(d,J=16.
4Hz,1H,CH2),2.
22(d,J=16.
4Hz,1H,CH2),2.
24-2.
01(m,2H,CH2),1.
06(s,3H,CH3),0.
91(s,3H,CH3),0.
87(t,J=15.
2Hz,3H,CH3).
13CNMR(100MHz,DMSO)δ:192.
1,172.
3,151.
7,148.
4,139.
6,137.
3,135.
8,134.
4,122.
5,108.
8,101.
2,68.
3,26.
4,24.
6,17.
2,16.
3,8.
9.
HRMS(ESI):m/zcalcdfor:C26H24BrNaNO5,532.
0731,found:532.
0717.
2-(benzo[d][1,3]dioxol-5-yl)-1-(4-bromophenyl)-4,5,6,7-tetrahydro-6,6-dimethyl-4-oxo-1H-indol-7-ylbutyrate4vThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,9:1,v/v)(Mp:147-149oC).
IR(KBr,,cm-1):1728,1681,1494,1475,1231,1165,1036,838,803,728.
1HNMR(400MHz,DMSO)δ:7.
71(d,J=8.
4Hz,1H,ArH),7.
55(d,J=8.
4Hz,1H,ArH),7.
44(d,J=8.
4Hz,1H,ArH),7.
01(d,J=8.
4Hz,1H,ArH),6.
81-6.
79(m,1H,ArH),6.
72(s,1H,ArH),6.
60(s,1H,ArH),6.
58(s,1H,OCH),5.
98(s,2H,CH2),5.
64(s,1H,CH),2.
60(d,J=16.
4Hz,1H,CH2),2.
21(d,J=16.
4Hz,1H,CH2),2.
23-1.
97(m,2H,CH2),1.
40-1.
38(m,2H,CH2),1.
06(s,3H,CH3),0.
92(s,3H,CH3),0.
79(t,J=14.
4Hz,3H,CH3).
13CNMR(100MHz,DMSO)δ:192.
1,171.
4,147.
1,146.
8,139.
6,135.
7,130.
3,124.
6,122.
5,108.
9,108.
2,104.
5,101.
2,68.
2,34.
7,25.
6,24.
7,17.
6,13.
4.
HRMS(ESI):m/zcalcdfor:C27H26BrNaNO5,546.
0887,found:546.
0892.
2-(benzo[d][1,3]dioxol-5-yl)-1-(4-bromophenyl)-4,5,6,7-tetrahydro-6,6-dimethyl-4-oxo-1H-indol-7-ylisobutyrate4wThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,9:1,v/v)(Mp:>184-186oC).
IR(KBr,,cm-1):1738,1666,1480,1456,1232,1143,1037,836,806,724.
1HNMR(400MHz,DMSO)δ:7.
71(d,J=7.
6Hz,1H,ArH),7.
55(d,J=7.
6Hz,1H,ArH),7.
47(d,J=7.
6Hz,1H,ArH),6.
96(d,J=7.
6Hz,1H,ArH),6.
81-6.
79(m,1H,ArH),6.
73(s,1H,ArH),6.
61(s,1H,ArH),6.
59(s,1H,OCH),5.
98(s,2H,CH2),5.
67(s,1H,CH),2.
62(d,J=16.
4Hz,1H,CH2),2.
21(d,J=16.
4Hz,1H,CH2),2.
35-2.
28(m,1H,CH2),1.
07(s,3H,CH3),1.
00(t,J=14.
4Hz,3H,CH3),0.
91(s,3H,CH3),0.
88(t,J=14.
4Hz,3H,CH3).
13CNMR(100MHz,DMSO)δ:192.
1,174.
7,147.
1,146.
8,139.
5,137.
3,135.
7,124.
6,122.
5,120.
9,108.
8,104.
5,101.
2,68.
1,47.
8,33.
1,25.
7,24.
6,19.
2,18.
3.
HRMS(ESI):m/zcalcdfor:C27H26BrNNaO5,546.
0887,found:546.
0892.
Generalprocedureforthesynthesisofbis-indoles5Exampleforthesynthesisof5a:6,7-dihydro-7-(4-hydroxy-2-phenyl-1-p-tolyl-1H-indol-3-yl)-2-phenyl-1-p-tolyl-1H-indol-4(5H)-oneMicrowaveHeating:Phenylglyoxalmonohydrate(1a,2.
2mmol,0.
34g,1.
1equiv.
)wasintroducedina10-mLInitiatorTMreactionvial,3-(p-tolylamino)cyclohex-2-enone(2g,2.
0mmol,0.
40g,1.
0equiv.
)andaceticacid(2mL,excess.
)werethensuccessivelyadded.
Subsequently,thereactionvialwascappedandthenpre-stirringfor20second.
Themixturewasirradiated(Time:20min,Temperature:100oC;AbsorptionLevel:High;FixedHoldTime)untilTLC(petroleumether:acetone3:1)revealedthatconversionofthestartingmaterial2gwascompleted.
Thereactionmixturewasthencooledtoroomtemperatureandthenstirredfor30min.
ThesolidproductwascollectedbyBüchnerfiltrationandwaspurifiedbyflashcolumnchromatography(silicagel,mixturesofpetroleumether/acetone,7:1,v/v)toaffordthedesiredpureproducts5aaswhitesolid(Mp:262-263oC).
IR(KBr,,cm-1):1643,1518,1462,1289,1185,1018,953,842,747,635.
1HNMR(400MHz,DMSO)δ:7.
31-7.
28(m,3H,ArH),7.
21-7.
02(m,6H,ArH),7.
00-6.
86(m,7H,ArH),6.
81-6.
79(m,6H,ArH),6.
59(d,J=8.
0Hz,1H,ArH),6.
51(d,J=7.
6Hz,1H,ArH),6.
45-6.
39(m,1H,ArH),6.
07(d,J=7.
6Hz,1H,ArH),4.
58-4.
53(m,1H,CH),3.
02-2.
91(m,1H,CH2),2.
78-2.
74(m,1H,CH2),2.
56-2.
52(m,1H,CH2),2.
35(s,3H,CH3),2.
29(s,3H,CH3).
13CNMR(100MHz,DMSO)δ:195.
6,194.
6,189.
9,149.
7,146.
7,136.
8,134.
9,130.
8,127.
9,127.
6,126.
8,123.
3,114.
0,107.
6,106.
2,106.
0,102.
8,95.
2,64.
0,41.
1,38.
2,33.
4,30.
9,24.
2,21.
2,21.
1,6.
01.
HRMS(ESI):m/zcalcdfor:C42H33N2O2,597.
2541,found:597.
2516.
2-(4-fluorophenyl)-7-(2-(4-fluorophenyl)-4-hydroxy-1-p-tolyl-1H-indol-3-yl)-6,7-dihydro-1-p-tolyl-1H-indol-4(5H)-one5bThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,7:1,v/v)(Mp:276-278oC).
IR(KBr,,cm-1):1629,1516,1453,1285,1158,1007,837,748,632,530.
1HNMR(400MHz,DMSO)δ:7.
10-6.
96(m,5H,ArH),6.
95-6.
86(m,5H,ArH),6.
80-6.
63(m,6H,ArH),6.
56(d,J=8.
4Hz,1H,ArH),6.
50(d,J=7.
6Hz,1H,ArH),6.
41-6.
40(m,1H,ArH),6.
01(d,J=7.
6Hz,1H,ArH),4.
47-4.
42(m,1H,CH),2.
97-2.
93(m,1H,CH2),2.
74-2.
71(m,1H,CH2),2.
48-2.
43(m,1H,CH2),2.
34(s,3H,CH3),2.
27(s,3H,CH3).
HRMS(ESI):m/zcalcdfor:C42H31F2N2O2,633.
2353,found:633.
2348.
2-(4-chlorophenyl)-7-(2-(4-chlorophenyl)-4-hydroxy-1-p-tolyl-1H-indol-3-yl)-6,7-dihydro-1-p-tolyl-1H-indol-4(5H)-one5cThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,7:1,v/v)(Mp:290-291oC).
IR(KBr,,cm-1):1631,1544,1452,1387,1284,1195,1095,959,833,746,631.
1HNMR(400MHz,DMSO)δ:7.
21-7.
02(m,5H,ArH),7.
00-6.
83(m,8H,ArH),6.
75-6.
64(m,3H,ArH),6.
57(d,J=8.
4Hz,1H,ArH),6.
47(d,J=7.
6Hz,1H,ArH),6.
42(d,J=8.
0Hz,1H,ArH),6.
00(d,J=8.
0Hz,1H,ArH),4.
47-4.
43(m,1H,CH),2.
94-2.
88(m,1H,CH2),2.
73-2.
70(m,1H,CH2),2.
48-2.
44(m,1H,CH2),2.
35(s,3H,CH3),2.
28(s,3H,CH3).
HRMS(ESI):m/zcalcdfor:C42H31Cl2N2O2,665.
1762,found:665.
1764.
2-(4-bromophenyl)-7-(2-(4-bromophenyl)-4-hydroxy-1-p-tolyl-1H-indol-3-yl)-6,7-dihydro-1-p-tolyl-1H-indol-4(5H)-one5dThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,7:1,v/v)(Mp:274-276oC).
IR(KBr,,cm-1):1632,1585,1432,1288,1185,1006,989,833,772,632.
1HNMR(400MHz,DMSO)δ:7.
43-7.
41(m,2H,ArH),7.
18-7.
07(m,5H,ArH),6.
95-6.
89(m,3H,ArH),6.
84-6.
73(m,5H,ArH),6.
57(d,J=8.
0Hz,1H,ArH),6.
50(d,J=8.
0Hz,1H,ArH),6.
42(d,J=8.
0Hz,1H,ArH),6.
01(d,J=8.
0Hz,1H,ArH),4.
47-4.
43(m,1H,CH),3.
02-2.
91(m,1H,CH2),2.
73-2.
71(m,1H,CH2),2.
47-2.
41(m,1H,CH2),2.
35(s,3H,CH3),2.
28(s,3H,CH3).
HRMS(ESI):m/zcalcdfor:C42H31Br2N2O2,753.
0752,found:753.
0752.
6,7-dihydro-7-(4-hydroxy-2-(4-methoxyphenyl)-1-p-tolyl-1H-indol-3-yl)-2-(4-methoxyphenyl)-1-p-tolyl-1H-indol-4(5H)-one5eThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,7:1,v/v)(Mp:269-270oC).
IR(KBr,,cm-1):1639,1507,1458,1272,1188,1012,949,839,712,623.
1HNMR(400MHz,DMSO)δ:7.
14-6.
98(m,3H,ArH),6.
92-6.
72(m,10H,ArH),6.
66-6.
55(m,4H,ArH),6.
47(d,J=8.
0Hz,1H,ArH),6.
39(d,J=8.
0Hz,1H,ArH),6.
00(d,J=7.
6Hz,1H,ArH),4.
51-4.
47(m,1H,CH),3.
82(s,3H,OCH3),3.
69(s,3H,OCH3),2.
91-2.
81(m,1H,CH2),2.
74-2.
70(m,2H,CH2),2.
51-2.
47(m,1H,CH2),2.
33(s,3H,CH3),2.
27(s,3H,CH3).
HRMS(ESI):m/zcalcdfor:C44H37N2O4,657.
2753,found:657.
2751.
6,7-dihydro-7-(4-hydroxy-2-(4-methoxyphenyl)-1-p-tolyl-1H-indol-3-yl)-2-(4-methoxyphenyl)-1-p-tolyl-1H-indol-4(5H)-one5fThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,7:1,v/v)(Mp:233-234oC).
IR(KBr,,cm-1):1632,1515,1452,1283,1195,1008,959,832,742,630.
1HNMR(400MHz,DMSO)δ:7.
23-7.
19(m,2H,ArH),7.
15-6.
75(m,10H,ArH),6.
68-6.
56(m,4H,ArH),6.
48-6.
36(m,4H,ArH),6.
05(d,J=8.
0Hz,1H,ArH),4.
61-4.
57(m,1H,CH),3.
70(s,3H,OCH3),3.
51(s,3H,OCH3),2.
91-2.
87(m,1H,CH2),2.
77-2.
72(m,2H,CH2),2.
52-2.
49(m,1H,CH2),2.
33(s,3H,CH3),2.
27(s,3H,CH3).
HRMS(ESI):m/zcalcdfor:C44H37N2O4,657.
2753,found:657.
2795.
1-(4-chlorophenyl)-7-(1-(4-chlorophenyl)-2-(4-fluorophenyl)-4-hydroxy-1H-indol-3-yl)-2-(4-fluorophenyl)-6,7-dihydro-1H-indol-4(5H)-one5gThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,7:1,v/v)(Mp:288-289oC).
IR(KBr,,cm-1):1627,1493,1461,1225,1196,1159,1090,1015,816,741,523.
1HNMR(400MHz,DMSO)δ:7.
41-7.
31(m,2H,ArH),7.
24-7.
16(m,2H,ArH),7.
07-6.
91(m,7H,ArH),6.
90-6.
66(m,5H,ArH),6.
56(d,J=8.
0Hz,1H,ArH),6.
55-6.
50(m,2H,ArH),6.
09-6.
06(m,1H,ArH),4.
50-4.
47(m,1H,CH),3.
07-3.
01(m,1H,CH2),2.
77-2.
75(m,1H,CH2),2.
52-2.
49(m,1H,CH2).
HRMS(ESI):m/zcalcdfor:C40H25Cl2F2N2O2,673.
1260,found:673.
1214.
1-(4-chlorophenyl)-7-(1-(4-chlorophenyl)-4-hydroxy-2-p-tolyl-1H-indol-3-yl)-6,7-dihydro-2-p-tolyl-1H-indol-4(5H)-one5hThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,7:1,v/v)(Mp:291-293oC).
IR(KBr,,cm-1):1639,1493,1458,1287,1192,1090,842,743,620.
1HNMR(400MHz,DMSO)δ:7.
33-7.
29(m,2H,ArH),7.
25-7.
15(m,3H,ArH),7.
07-7.
05(m,2H,ArH),7.
00-6.
75(m,9H,ArH),6.
56(d,J=8.
4Hz,1H,ArH),6.
46(d,J=8.
0Hz,1H,ArH),6.
50-6.
44(m,1H,ArH),6.
09(d,J=8.
0Hz,1H,ArH),4.
57-4.
53(m,1H,CH),3.
02-2.
97(m,1H,CH2),2.
77-2.
75(m,1H,CH2),2.
57-2.
53(m,1H,CH2),2.
37(s,3H,CH3),2.
21(s,3H,CH3).
HRMS(ESI):m/zcalcdfor:C42H31Cl2N2O2,665.
1762,found:665.
1751.
2-(benzo[d][1,3]dioxol-5-yl)-7-(2-(benzo[d][1,3]dioxol-6-yl)-1-(4-chlorophenyl)-4-hydroxy-1H-indol-3-yl)-1-(4-chlorophenyl)-6,7-dihydro-1H-indol-4(5H)-one5iThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,7:1,v/v)(Mp:280-284oC).
IR(KBr,,cm-1):1633,1518,1442,1253,1152,1019,979,846,746,638.
1HNMR(400MHz,DMSO)δ:7.
41-7.
32(m,2H,ArH),7.
07-7.
03(m,2H,ArH),6.
93-6.
91(m,1H,ArH),6.
85-6.
76(m,5H,ArH),6.
54-6.
49(m,5H,ArH),6.
40-6.
38(m,2H,ArH),6.
13(d,J=8.
8Hz,1H,ArH),6.
02(s,2H,CH2),5.
85(s,2H,CH2),4.
55-4.
51(m,1H,CH),3.
06-3.
01(m,1H,CH2),2.
78-2.
77(m,2H,CH2),2.
52-2.
48(m,1H,CH2).
HRMS(ESI):m/zcalcdfor:C42H27Cl2N2O6,725.
1245,found:725.
1246.
1-(4-fluorophenyl)-7-(1-(4-fluorophenyl)-4-hydroxy-2-phenyl-1H-indol-3-yl)-6,7-dihydro-2-phenyl-1H-indol-4(5H)-one5jThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,7:1,v/v)(Mp:267-270oC).
IR(KBr,,cm-1):1636,1514,1457,1273,1195,1029,978,812,748,633.
1HNMR(400MHz,DMSO)δ:7.
33-7.
30(m,3H,ArH),7.
23-7.
19(m,3H,ArH),7.
09-6.
95(m,5H,ArH),6.
93-6.
75(m,7H,ArH),6.
53(d,J=8.
0Hz,1H,ArH),6.
46(d,J=8.
0Hz,1H,ArH),6.
25-6.
13(m,2H,ArH),4.
59-4.
55(m,1H,CH),2.
99-2.
96(m,1H,CH2),2.
77-2.
74(m,2H,CH2),2.
57-2.
55(m,1H,CH2).
HRMS(ESI):m/zcalcdfor:C40H27F2N2O2,605.
2040,found:605.
2045.
2-(benzo[d][1,3]dioxol-5-yl)-7-(2-(benzo[d][1,3]dioxol-6-yl)-1-(4-fluorophenyl)-4-hydroxy-1H-indol-3-yl)-1-(4-fluorophenyl)-6,7-dihydro-1H-indol-4(5H)-one5kThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,9:1,v/v)(Mp:184-186oC).
IR(KBr,,cm-1):1636,1511,1452,1243,1195,1007,957,852,792,638.
1HNMR(400MHz,DMSO)δ:7.
06-6.
89(m,5H,ArH),6.
85-6.
76(m,4H,ArH),6.
55-6.
39(m,6H,ArH),6.
25-6.
6.
18(m,3H,ArH),6.
01(s,2H,CH2),5.
84(s,2H,CH2),4.
55-4.
51(m,1H,CH),3.
01-2.
92(m,1H,CH2),2.
76-2.
75(m,2H,CH2),2.
50-2.
46(m,1H,CH2).
HRMS(ESI):m/zcalcdfor:C42H27F2N2O6,693.
1836,found:693.
1835.
6,7-dihydro-7-(4-hydroxy-1-(4-methoxyphenyl)-2-phenyl-1H-indol-3-yl)-1-(4-methoxyphenyl)-2-phenyl-1H-indol-4(5H)-one5lThetitlecompoundwaspreparedfollowingthegeneralprocedure(microwaveheating)andwasobtainedasawhitesolidafterpurificationbysilicagelcolumnchromatography(petroleumether/acetone,7:1,v/v)(Mp:267-269oC).
IR(KBr,,cm-1):1637,1512,1472,1288,1196,1005,969,839,743,631.
1HNMR(400MHz,DMSO)δ:7.
29-7.
26(m,3H,ArH),7.
19-7.
00(m,5H,ArH),6.
96-6.
76(m,7H,ArH),6.
65-6.
63(m,3H,ArH),6.
52(d,J=8.
0Hz,1H,ArH),6.
45(d,J=7.
6Hz,1H,ArH),6.
10-6.
02(m,2H,ArH),4.
56-4.
51(m,1H,CH),3.
79(s,3H,OCH3),3.
72(s,3H,OCH3),2.
94-2.
91(m,1H,CH2),2.
80-2.
67(m,2H,CH2),2.
53-2.
51(m,1H,CH2).
HRMS(ESI):m/zcalcdfor:C42H33N2O4,629.
2440,found:629.
2480.
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