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
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
收藏
页码:2791 / 2793
页数:3
相关论文
共 31 条