Direct N- and C-alkenylation of nitrogen-containing heterocycles with magnesium alkylidene carbenoids

被引：23

作者：

Sakurada, Jo ^{[1
]}

Satoh, Tsuyoshi ^{[1
]}

机构：

[1] Tokyo Univ Sci, Fac Sci, Dept Chem, Tokyo 1620826, Japan

来源：

TETRAHEDRON | 2007年 / 63卷 / 18期

关键词：

sulfoxide-magnesium exchange reaction; magnesium alkylidene carbenoid; alkenylation; N-alkenylation of heterocycles; C-alkenylation of heterocycles;

D O I：

10.1016/j.tet.2007.02.072

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of magnesium alkylidene carbenoids, which were generated from 1-chlorovinyl p-tolyl sulfoxides with isopropylmagnesium chloride at -78 degrees C in toluene, with N-lithio nitrogen-containing heterocycles gave N-alkenylated products in moderate to good yields. Also, the reaction of C-lithio indoles, which were generated from N-protected indoles, with magnesium alkylidene carbenoids gave C-2 or C-3 alkenylated products, corresponding to the protective group. The intermediate of these reactions were found to be the alkenyl anion, which could be trapped with electrophiles to give the heterocycles having fully substituted alkenes. (C) 2007 Elsevier Ltd. All rights reserved.

引用

页码：3806 / 3817

页数：12

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