Application of 2-substituted vinamidinium salts to the synthesis of 2,4-disubstituted pyrroles

Abstract

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.