A convenient, eco-friendly, and efficient method for synthesis of bis(3-indolyl)methanes "on-water"

被引:16
作者
Mallik, Asok K. [1 ]
Pal, Rammohan [1 ]
Guha, Chayan [1 ]
Mallik, Haimanti [2 ]
机构
[1] Jadavpur Univ, Dept Chem, Kolkata 700032, India
[2] Lady Brabourne Coll, Dept Chem, Kolkata 700017, India
关键词
bis(3-indolyl)methanes; synthesis; indoles; aromatic aldehydes; on-water; CATALYZED-REACTIONS; FACILE SYNTHESIS; ACID; BIS(INDOLYL)METHANES; ALCOHOLS; INDOLES; MILD; DIINDOLYLMETHANES; BACTERIUM; ALDEHYDES;
D O I
10.1080/17518253.2011.630027
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A convenient, eco-friendly, and efficient method for synthesis of bis(3-indolyl)methanes by the reaction of indoles with various aromatic aldehydes "on-water" has been developed. The attractive features of this method are that in cases of aldehydes which are easily oxidized to acids, no external catalyst is necessary while in other cases a trace amount (ca. 5 mol%) of commercially available and inexpensive catalyst benzoic acid is sufficient to give good to excellent yield of products.
引用
收藏
页码:321 / 327
页数:7
相关论文
共 35 条
[1]   TRYPTOPHAN ANALOGS FORM ADDUCTS BY COOPERATIVE REACTION WITH ALDEHYDES AND ALCOHOLS OR WITH ALDEHYDES ALONE - POSSIBLE ROLE IN ETHANOL TOXICITY [J].
AUSTIN, JE ;
FRAENKELCONRAT, H .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1992, 89 (18) :8439-8442
[2]   VIBRINDOLE-A, A METABOLITE OF THE MARINE BACTERIUM, VIBRIO-PARAHAEMOLYTICUS, ISOLATED FROM THE TOXIC MUCUS OF THE BOXFISH OSTRACION-CUBICUS [J].
BELL, R ;
CARMELI, S ;
SAR, N .
JOURNAL OF NATURAL PRODUCTS-LLOYDIA, 1994, 57 (11) :1587-1590
[3]  
C-J Li, 1997, ORGANIC REACTIONS AQ, P1
[4]   Lewis acid-catalyzed reactions in protic media. Lanthanide-catalyzed reactions of indoles with aldehydes or ketones [J].
Chen, DP ;
Yu, LB ;
Wang, PG .
TETRAHEDRON LETTERS, 1996, 37 (26) :4467-4470
[5]   A rational approach towards the nucleophilic substitutions of alcohols "on Water" [J].
Cozzi, Pier Giorgio ;
Zoli, Luca .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (22) :4162-4166
[6]   Nucleophilic substitution of ferrocenyl alcohols "on water'' [J].
Cozzi, Pier Giorgio ;
Zoli, Luca .
GREEN CHEMISTRY, 2007, 9 (12) :1292-1295
[7]   An efficient and clean synthesis of bis(indolyl)methanes in a protic solvent at room temperature [J].
Deb, WL ;
Bhuyan, PJ .
TETRAHEDRON LETTERS, 2006, 47 (09) :1441-1443
[8]   STEREOCONTROLLED SYNTHESIS OF (-)-HAPALINDOLE-G [J].
FUKUYAMA, T ;
CHEN, XQ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (07) :3125-3126
[9]   Facile and Mild Synthesis of bis(3-Indolyl)methanes [J].
Ghorbani-Vaghei, R. ;
Malaekehpoor, S. M. .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2010, 42 (02) :175-182
[10]  
Giannini G., 2000, CHEM ABSTR, V136