New carbanionic access to 3-vinylindoles and 3-vinylbenzofurans

被引：45

作者：

Le Strat, F ^{[1
]}

Maddaluno, J ^{[1
]}

机构：

[1] Univ Rouen, UMR 6014 CNRS, IRCOF, Lab Fonct Azotees & Oxygenees Complexes, F-76821 Mont St Aignan, France

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 16期

关键词：

D O I：

10.1021/ol026351v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A simple route to 3-vinylbenzofurans, 3-vinyifuropyridines, and 3-vinylindoles from readily accessible acetylenic precursors is described. A standard halogen-lithium exchange triggers an irreversible! addition on the triple bond, according to a 5-exo-dig heterocyclization process, followed by a lithium ethoxide elimination. A final isomerization of the exocyclic allene provides a 1,3-dienic system that can react with acrylates, in thermal or hyperbaric conditions, to provide the expected [4+2] cycloadducts.

引用

页码：2791 / 2793

页数：3

共 31 条

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