HOMOLYTIC SUBSTITUTION-REACTIONS OF ELECTRON-RICH PENTATOMIC HETEROAROMATICS BY ELECTROPHILIC CARBON-CENTERED RADICALS - SYNTHESIS OF ALPHA-HETEROARYLACETIC ACIDS

被引：67

作者：

BACIOCCHI, E ^{[1
]}

MURAGLIA, E ^{[1
]}

SLEITER, G ^{[1
]}

机构：

[1] UNIV ROME LA SAPIENZA,CNR,CTR STUDIO MECCAN REAZ,I-00185 ROME,ITALY

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 25期

关键词：

D O I：

10.1021/jo00051a027

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Efficient and selective homolytic substitutions (yields between 55 and 90%) of pyrrole, indole, and some pyrrole derivatives have been carried out using ambiphilic and electrophilic carbon centered radicals, generated in DMSO by Fe2+/H2O2 and alpha-cyano-, alpha-carbonyl-, and alpha,alpha'-dicarbonylalkyl iodides. The reaction is highly successful also with pyrroles substituted by electron-withdrawing groups, which has allowed an efficient synthesis of Tolmetin. A few extensions of this reaction to furan and thiophene are described.

引用

页码：6817 / 6820

页数：4