Dry reaction of indoles with carbonyl compounds on montmorillonite K10 clay: a mild, expedient synthesis of diindolylalkanes and vibrindole A

被引：205

作者：

Chakrabarty, M

Ghosh, N

Basak, R

Harigaya, Y

机构：

[1] Bose Inst, Dept Chem, Kolkata 700009, W Bengal, India

[2] Kitasato Univ, Sch Pharmaceut Sci, Minato Ku, Tokyo 108, Japan

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 22期

关键词：

diindolylalkanes; vibrindole A; green synthesis; clay;

D O I：

10.1016/S0040-4039(02)00682-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Dry reaction of indoles 1a-c with aldehydes 2a-i. ketones 2j-o and an acetal 2p on M. K10 clay at room temperature furnished 3,3'-diindolylalkanes (DIAs: 3a-h, j-r). The novel formation of tris(3-indolyl)methane 4 from 2i through tandem reactions and of the DIAs 6 and 8 from 1d through Plancher rearrangements were also observed. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：4075 / 4078

页数：4

共 28 条

[1] REACTIONS OF ELECTRON-RICH HETEROCYCLICS WITH ORTHO-CARBOXYLIC ACID-DERIVATIVES .1. THE REACTION BEHAVIOR OF ACYCLIC ORTHO-ESTERS WITH INDOLES USING ACID CATALYSIS
AKGUN, E
PINDUR, U
MULLER, J
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1983, 20 (05) : 1303 - 1305
[2] BALMER CT, 1965, J MED CHEM, V8, P397
[3] VIBRINDOLE-A, A METABOLITE OF THE MARINE BACTERIUM, VIBRIO-PARAHAEMOLYTICUS, ISOLATED FROM THE TOXIC MUCUS OF THE BOXFISH OSTRACION-CUBICUS
BELL, R
CARMELI, S
SAR, N
[J]. JOURNAL OF NATURAL PRODUCTS-LLOYDIA, 1994, 57 (11): : 1587 - 1590
[4] New bisindole alkaloids of the topsentin and hamacanthin classes from the Mediterranean marine sponge Rhaphisia lacazei
Casapullo, A
Bifulco, G
Bruno, I
Riccio, R
[J]. JOURNAL OF NATURAL PRODUCTS, 2000, 63 (04): : 447 - 451
[5] Novel clay-mediated, tandem addition-elimination-(Michael) addition reactions of indoles with 3-formylindole: an eco-friendly route to symmetrical and unsymmetrical triindolylmethanes
Chakrabarty, M
Sarkar, S
[J]. TETRAHEDRON LETTERS, 2002, 43 (07) : 1351 - 1353
[6] Chakrabarty M, 2001, HETEROCYCLES, V55, P2431
[7] 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
Chakrabarty, M
Basak, R
Ghosh, N
[J]. TETRAHEDRON LETTERS, 2001, 42 (23) : 3913 - 3915
[8] The reactions of nitrones with indoles
Chalaye-Mauger, H
Denis, JN
Averbuch-Pouchot, MT
Vallée, Y
[J]. TETRAHEDRON, 2000, 56 (05) : 791 - 804
[9] Lewis acid-catalyzed reactions in protic media. Lanthanide-catalyzed reactions of indoles with aldehydes or ketones
Chen, DP
Yu, LB
Wang, PG
[J]. TETRAHEDRON LETTERS, 1996, 37 (26) : 4467 - 4470
[10] Ciamician G., 1896, CHEM BER, V29, P2475

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