SYNTHESIS OF (INDOL-3-YLMETHYL)TRIMETHYLSILANES BY MEANS OF ALUMINA-MEDIATED ALKYLATION OF INDOLES WITH ALPHA-CHLORO-ALPHA-SILYLSULFIDES

被引:5
作者
ISHIBASHI, H
NISHIDA, K
IKEDA, M
机构
[1] Kyoto Pharmaceutical University, Misasagi, Yamashina
关键词
D O I
10.1080/00397919308011123
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of a mixture of indoles and alpha-chloro-alpha-silylsulfide 6 with neutral chromatographic alumina afforded the aromatic substitution products 8, which were desurfurized with Bu3SnH and AIBN to give (indol-3-ylmethyl)trimethylsilanes 9.
引用
收藏
页码:2381 / 2387
页数:7
相关论文
共 7 条
[1]   NEW SYNTHETIC APPROACH TO 4-ALKYLIDENECYCLOHEXENES - REDUCTION-PROTODESILYLATION OF BENZYLSILANES [J].
COUGHLIN, DJ ;
SALOMON, RG .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (22) :3784-3790
[2]   A NEW SYNTHESIS OF VINYL SULFIDES BY LEWIS ACID PROMOTED REACTION OF [CHLORO(ARYLTHIO)METHYL]TRIMETHYLSILANES WITH TRISUBSTITUTED ALKENES [J].
ISHIBASHI, H ;
NAKATANI, H ;
SAKASHITA, H ;
IKEDA, M .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (05) :338-340
[3]   REACTION OF [ARYLTHIO(CHLORO)METHYL]TRIMETHYLSILANES WITH ARENES AND ALK-1-ENES IN THE PRESENCE OF LEWIS ACID - SYNTHESES OF [ARYL(ARYLTHIO)METHYL]-AND (1-ARYLTHIOALK-3-ENYL)-TRIMETHYLSILANES [J].
ISHIBASHI, H ;
NAKATANI, H ;
UMEI, Y ;
YAMAMOTO, W ;
IKEDA, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (03) :589-593
[4]   C-ALKYLATIONS OF INDOLES AND PYRROLES WITH ALPHA-CHLOROSULFIDES ON AN ALUMINA SURFACE - A SHORT SYNTHESIS OF DITHYREANITRILE [J].
ISHIBASHI, H ;
MITA, N ;
MATSUBA, N ;
KUBO, T ;
NAKANISHI, M ;
IKEDA, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (21) :2821-2825
[5]   ORGANIC-REACTIONS AT ALUMINA SURFACES [J].
POSNER, GH .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1978, 17 (07) :487-496
[6]   FLUORIDE-ION INDUCED REACTIONS OF ORGANOSILANES WITH SATURATED LACTONES AND ALPHA,BETA-ENONES [J].
RICCI, A ;
FIORENZA, M ;
GRIFAGNI, MA ;
BARTOLINI, G .
TETRAHEDRON LETTERS, 1982, 23 (48) :5079-5082
[7]   STEREOCONTROLLED SYNTHESIS OF (+/-)-DEOXYPODOPHYLLOTOXIN VIA THE BENZYL EQUIVALENT OF THE PETERSON REACTION [J].
TAKANO, S ;
OTAKI, S ;
OGASAWARA, K .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (08) :485-487