Facile synthesis of bis(indolyl)methanes using catalytic amount of iodine at room temperature under solvent-free conditions

被引:298
作者
Ji, SJ [1 ]
Wang, SY
Zhang, Y
Loh, TP
机构
[1] Suzhou Univ, Coll Chem & Chem Engn, Suzhou 215006, Peoples R China
[2] Suzhou Univ, Key Lab Organ Synth Jiangsu Prov, Suzhou 215006, Peoples R China
[3] Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore
基金
中国国家自然科学基金;
关键词
solvent-free; iodine; indoles; aldehydes; bis(indolyl)methanes;
D O I
10.1016/j.tet.2003.12.060
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Efficient electrophilic substitution reactions of indoles with various aromatic aldehydes were carried out using a catalytic amount of I-2 under solvent-free conditions to afford the corresponding bis(indolyl)methanes in excellent yields. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2051 / 2055
页数:5
相关论文
共 30 条
[1]  
[Anonymous], 1996, CHEM INDOLES
[2]   A convenient method of synthesis of bis-indolylmethanes:: Indium trichloride catalyzed reactions of indole with aldehydes and Schiff's bases. [J].
Babu, G ;
Sridhar, N ;
Perumal, PT .
SYNTHETIC COMMUNICATIONS, 2000, 30 (09) :1609-1614
[3]   Molecular iodine-catalyzed efficient and highly rapid synthesis of bis(indolyl)methanes under mild conditions [J].
Bandgar, BP ;
Shaikh, KA .
TETRAHEDRON LETTERS, 2003, 44 (09) :1959-1961
[4]   LEWIS ACID-INDUCED ELECTROPHILIC SUBSTITUTION OF INDOLE .3. [J].
BANERJI, J ;
CHATTERJEE, A ;
MANNA, S ;
PASCARD, C ;
PRANGE, T ;
SHOOLERY, JN .
HETEROCYCLES, 1981, 15 (01) :325-336
[5]  
Basu MK, 2002, SYNLETT, P319
[6]   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
[7]   FURTHER BROMINATED BIS-INDOLE AND TRIS-INDOLE ALKALOIDS FROM THE DEEP-WATER NEW-CALEDONIAN MARINE SPONGE ORINA SP [J].
BIFULCO, G ;
BRUNO, I ;
RICCIO, R ;
LAVAYRE, J ;
BOURDY, G .
JOURNAL OF NATURAL PRODUCTS-LLOYDIA, 1995, 58 (08) :1254-1260
[8]   Solvent and catalyst free three-component coupling of carbonyl compounds, amines and triethylphosphite;: a new synthesis of α-aminophosphonates [J].
Chandrasekhar, S ;
Narsihmulu, C ;
Sultana, SS ;
Saritha, B ;
Prakash, SJ .
SYNLETT, 2003, (04) :505-506
[9]   LEWIS-ACID-INDUCED ELECTROPHILIC SUBSTITUTION IN INDOLES WITH ACETONE .2. [J].
CHATTERJEE, A ;
MANNA, S ;
BANERJI, J ;
PASCARD, C ;
PRANGE, T ;
SHOOLERY, JN .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (02) :553-555
[10]   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