InCl3-catalysed conjugate addition of indoles with electron-deficient olefins

被引:177
作者
Yadav, JS [1 ]
Abraham, S [1 ]
Reddy, BVS [1 ]
Sabitha, G [1 ]
机构
[1] Indian Inst Chem Technol, Div Organ Chem, Hyderabad 500007, Andhra Pradesh, India
来源
SYNTHESIS-STUTTGART | 2001年 / 14期
关键词
indium trichloride; indole; alpha; beta-unsaturated compounds; addition reactions;
D O I
10.1055/s-2001-18068
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Indole and 2-methylindole undergo conjugate addition with electron-deficient olefins in the presence of a catalytic amount of InCl3 at ambient temperature to afford the corresponding Michael adducts in excellent yields with high selectivity.
引用
收藏
页码:2165 / 2169
页数:5
相关论文
共 11 条
[1]  
[Anonymous], 1996, CHEM INDOLES
[2]  
Babu G, 2000, ALDRICHIM ACTA, V33, P16
[3]   ADDITION AND ANNULATION REACTIONS BETWEEN INDOLES AND ALPHA,BETA-UNSATURATED KETONES [J].
GARNICK, RL ;
LEVERY, SB ;
LEQUESNE, PW .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (06) :1226-1229
[4]   The ultra high pressure conjugate addition of indoles to electron-deficient olefins [J].
Harrington, P ;
Kerr, MA .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1998, 76 (09) :1256-1265
[5]   Reaction of indoles with electron deficient olefins catalyzed by Yb(OTf)(3).3H(2)O [J].
Harrington, PE ;
Kerr, MA .
SYNLETT, 1996, (11) :1047-+
[6]   REACTIONS ON SOLID SUPPORTS .4. REACTIONS OF ALPHA-BETA-UNSATURATED CARBONYL-COMPOUNDS WITH INDOLES USING CLAY AS CATALYST [J].
IQBAL, Z ;
JACKSON, AH ;
RAO, KRN .
TETRAHEDRON LETTERS, 1988, 29 (21) :2577-2580
[7]   Indium trichloride (InCl3) catalysed Diels-Alder reaction in water [J].
Loh, TP ;
Pei, J ;
Lin, M .
CHEMICAL COMMUNICATIONS, 1996, (20) :2315-2316
[8]  
Loh TP, 1998, SYNLETT, P975
[9]   HAPALINDOLES - NEW ALKALOIDS FROM THE BLUE-GREEN-ALGA HAPALOSIPHON-FONTINALIS [J].
MOORE, RE ;
CHEUK, C ;
PATTERSON, GML .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (21) :6456-6457
[10]   HAPALINDOLES, ANTIBACTERIAL AND ANTIMYCOTIC ALKALOIDS FROM THE CYANOPHYTE HAPALOSIPHON-FONTINALIS [J].
MOORE, RE ;
CHEUK, C ;
YANG, XQG ;
PATTERSON, GML ;
BONJOUKLIAN, R ;
SMITKA, TA ;
MYNDERSE, JS ;
FOSTER, RS ;
JONES, ND ;
SWARTZENDRUBER, JK ;
DEETER, JB .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (06) :1036-1043