APPLICATION OF 2-SUBSTITUTED VINAMIDINIUM SALTS TO THE SYNTHESIS OF 2,4-DISUBSTITUTED PYRROLES

被引:89
作者
GUPTON, JT [1 ]
KROLIKOWSKI, DA [1 ]
YU, RH [1 ]
RIESINGER, SW [1 ]
SIKORSKI, JA [1 ]
机构
[1] MONSANTO AGR CO,DIV TECHNOL,ST LOUIS,MO 63167
关键词
D O I
10.1021/jo00302a047
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A variety of 2-substituted vinamidinium salts react with a-amino acid esters under basic conditions to produce 2-carbethoxy-4-substituted-pyrroles in good yield. The overall process represents a short and efficient synthesis of highly functionalized pyrroles from a-substituted acetic acid precursors. Such reactions may involve the intermediacy of azomethine ylids or “pentadienyl like” anions. © 1990, American Chemical Society. All rights reserved.
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页码:4735 / 4740
页数:6
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