SUBSTITUTION, OXIDATION AND ADDITION-REACTIONS AT C-7 OF ACTIVATED INDOLES

被引：60

作者：

BLACK, DS

BOWYER, MC

CATALANO, MM

IVORY, AJ

KELLER, PA

KUMAR, N

NUGENT, SJ

机构：

[1] School of Chemistry, University of New South Wales, Sydney

来源：

TETRAHEDRON | 1994年 / 50卷 / 35期

关键词：

D O I：

10.1016/S0040-4020(01)89590-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

4,6-Dimethoxy-2,3-diphenylindole (1) undergoes acylation, bromination, oxidative coupling and acid-catalysed addition to aldehydes at C-7 to produce a range of 7-substituted indoles (3-11), the indolo-isatin (6), the 7,7'-bi-indolyls (14), (16), (18), and the 7,7'-di-indolylmethanes (20-31). Addition to cyclopentanone gave compound (32), while Michael addition to alpha,beta-unsaturated ketones gave compound (33) and the non-benzenoid double adduct (34). Related reactions led to the formation of the ring-fused indoles (39) and (41). Some reactions of the related indole diester (2) are also reported.

引用

页码：10497 / 10508

页数：12

共 13 条

[1]

Black D.StC, 1990, J P ROY SOC NS WALES, V123, P1

[2]

BLACK DS, 1993, SYNLETT, P246

[3]

BLACK DS, 1989, SYNTHESIS-STUTTGART, P322

[4] PALLADIUM-CATALYZED INTRAMOLECULAR CYCLIZATION OF 7-HALO-N-ALLYL-INDOLES [J].