Synthesis of (Z)-N-(2-amino-1, 2-dicyanovinyl) formamide O-alkyloximes and a study of their cyclization in the presence of base

BL Booth, FAT Costa, RG Pritchard…

Index: Booth, Brian L.; Costa, Flora A. T.; Mahmood, Zahid; Pritchard, Robin G.; Proenca, M. Fernanda Journal of the Chemical Society - Perkin Transactions 1, 1999 , # 13 p. 1853 - 1858

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Citation Number: 19

Abstract

The title compounds (3) have been prepared in high yield by reaction of (Z [])-N-(2-amino-1, 2-dicyanovinyl) formimidate with an alkoxyamine NH2OR (R= CH2Ph, Me). These compounds cyclize to the corresponding 5-amino-4-cyanoimidazoles 4 by reaction with ethanolic NaOH solution. In ethyl acetate and using DBU as a base,