Intramolecular N-acyliminium ion versus Friedel-Crafts cyclization onto 3-indoles: synthesis of the novel rings pyrrolizino[2,1-b]indole and homologues

被引：13

作者：

Cincinelli, Raffaella ^{[1
]}

Dallavalle, Sabrina ^{[1
]}

Merlini, Lucio ^{[1
]}

Nannei, Raffaella ^{[1
]}

Scaglioni, Leonardo ^{[1
]}

机构：

[1] Univ Milan, Dipartimento Sci Mol Agroalimentari, I-20133 Milan, Italy

来源：

TETRAHEDRON | 2009年 / 65卷 / 17期

关键词：

Friedel-Crafts; Acyliminium ion; Indole-fused heterocycles; Synthesis; 4-SUBSTITUTED BETA-CARBOLIN-1-ONES; REACTIVITY;

D O I：

10.1016/j.tet.2009.02.036

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Acid treatment of indole-2-carboxylic acid beta- and gamma-oxoamides causes Friedel-Crafts intramolecular cyclization to beta-carbolinones and dihydro-2H-azepino[3,4-b]indol-1-ones, in contrast to secondary delta-, epsilon- and zeta-oxoamides, which cyclize to the novel heterocyclic rings pyrrolizino[2,1-b]indole, indolizino[2,1-b]indole, and 9a,11-diaza-indeno[1,2-a]azulene, via an intermediate N-acyliminium ion. Tertiary amides lead only the Friedel-Crafts ring closure, thus allowing the synthesis of larger fused rings. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：3465 / 3472

页数：8

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