Novel clay-mediated, tandem addition-elimination-(Michael) addition reactions of indoles with 3-formylindole: an eco-friendly route to symmetrical and unsymmetrical triindolylmethanes

被引：78
作者：
Chakrabarty, M [1 ]
Sarkar, S [1 ]
机构：
[1] Bose Inst, Dept Chem, Kolkata 700009, India
来源：
TETRAHEDRON LETTERS | 2002年 / 43卷 / 07期
关键词：
condensation; 3-formylindole; (alkyl)indoles; clay; triindolylmethanes;
D O I：
10.1016/S0040-4039(01)02380-2
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Dry reaction of 3-formylindole (1) with indole (2a) on Montmorillonite K10 clay at room temperature furnished within minutes tris(indol-3-yl)methane (3a) in high yield. The reaction of 1 with other mono- and dialkylindoles (2b-c, skatole. 8a-c) under similar conditions yielded either or both of symmetrical (3b c. 9) and unsymmetrical (4b c. 5b c. 10, 11a-c) triindolylmethanes, (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：1351 / 1353
页数：3
相关论文
共 18 条
[1]   STYRYLQUINOLINE ANALOGS FROM HETEROCYCLIC CARBOXALDEHYDES [J].
BAHNER, CT ;
KINDER, H ;
GUTMAN, L .
JOURNAL OF MEDICINAL CHEMISTRY, 1965, 8 (03) :397-&
[2]  
Basiuk V. A., 1995, RUSS CHEM REV+, V64, P1003
[3]  
BRAM G, 1992, SOLID SUPPORTS CATAL, P302
[4]  
BRAM G, 1987, PREPARATIVE CHEM USI, P387
[5]   Microwave-assisted Michael reactions of 3-(2′-nitrovinyl)indole with indoles on TLC-grade silica gel.: A new, facile synthesis of 2,2-bis(3′-indolyl)nitroethanes [J].
Chakrabarty, M ;
Basak, R ;
Ghosh, N .
TETRAHEDRON LETTERS, 2001, 42 (23) :3913-3915
[6]  
Clark J.H., 1994, CATALYSIS ORGANIC RE
[7]  
CORELIS A, 1994, SYNLETT, P155
[8]   HEIGHTENED SELECTIVITY IN AROMATIC NITRATIONS AND CHLORINATIONS BY THE USE OF SOLID SUPPORTS AND CATALYSTS [J].
DELAUDE, L ;
LASZLO, P ;
SMITH, K .
ACCOUNTS OF CHEMICAL RESEARCH, 1993, 26 (12) :607-613
[9]   Organic chemistry on solid supports [J].
Fruchtel, JS ;
Jung, G .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (01) :17-42
[10]   Indolyl carboxylic acids by condensation of indoles with α-keto acids [J].
Garbe, TR ;
Kobayashi, M ;
Shimizu, N ;
Takesue, N ;
Ozawa, M ;
Yukawa, H .
JOURNAL OF NATURAL PRODUCTS, 2000, 63 (05) :596-598
12