Rapid route to 3,4-substituted Indoles via a directed ortho metalation - Retro-Mannich sequence

被引：55

作者：

Chauder, B ^{[1
]}

Larkin, A ^{[1
]}

Snieckus, V ^{[1
]}

机构：

[1] Queens Univ, Dept Chem, Kingston, ON K7L 3N6, Canada

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 05期

关键词：

D O I：

10.1021/ol017310m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] In the presence of NXS (X = Br, I, Cl), gramine derivatives 1, derived by combined directed ortho metalation (DoM)-cross-coupling sequences, rapidly undergo retro-Mannich fragmentation (2) to afford 3-halo indoles 3 in 37-88% yields. A conceptually new methodology to diverse 3,4-substituted indoles (10, 11, 13) is thereby introduced.

引用

页码：815 / 817

页数：3

共 15 条

[1]

Amat M, 1996, HETEROCYCLES, V43, P1713

[2]

Baker SR, 1998, TETRAHEDRON LETT, V39, P331

[3] A mild and effective iodination method using iodine in the presence of bis-(trifluoroacetoxy)iodobenzene [J].