Efficient synthesis of bis(indolyl)methanes catalyzed by Lewis acids in ionic liquids

被引:152
作者
Ji, SJ [1 ]
Zhou, JF
Gu, DG
Wang, SY
Loh, TP
机构
[1] Suzhou Univ, Coll Chem & Chem Engn, Suzhou 215006, Peoples R China
[2] Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore
关键词
ionic liquids; In(OTf)3; Lewis acids; indoles; bis(indolyl)methanes;
D O I
10.1055/s-2003-41464
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 aldehydes proceed smoothly in ionic liquids using Lewis acids, In(OTf)(3), YbCl3, InCl3, BiCl3, and ZnCl2, to afford the corresponding bis(indolyl)methanes in high yields.
引用
收藏
页码:2077 / 2079
页数:3
相关论文
共 27 条
[1]   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
[2]   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
[3]   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
[4]   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
[5]   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
[6]   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
[7]   Asymmetric Mannich-type reactions catalyzed by indium(III) complexes in ionic liquids [J].
Chen, SL ;
Ji, SJ ;
Loh, TP .
TETRAHEDRON LETTERS, 2003, 44 (11) :2405-2408
[8]   6-BROMOTRYPTAMINE DERIVATIVES FROM THE GULF OF CALIFORNIA TUNICATE DIDEMNUM-CANDIDUM [J].
FAHY, E ;
POTTS, BCM ;
FAULKNER, DJ ;
SMITH, K .
JOURNAL OF NATURAL PRODUCTS, 1991, 54 (02) :564-569
[9]   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
[10]   REDUCTIVE C-ALKYLATION [J].
GREGOROV.BV ;
LIANG, KSY ;
CLUGSTON, DM ;
MACDONAL.SF .
CANADIAN JOURNAL OF CHEMISTRY, 1968, 46 (21) :3291-&