Purines, pyrimidines, and imidazoles. Part XXXIX. Formation of some 5-aminoimidazole-4-carboxylic acid derivatives from ethyl α-amino-α-cyanoacetate

Abstract

Dimerisation of ethyl α-amino-α-cyanoacetate has been found to yield diethyl 5-aminoimidazole-2,4-dicarboxylate. The amino-ester also reacts with triethyl orthoformate to produce, according to the conditions, ethyl N-(α-cyano-α-ethoxycarbonylmethyl)formimidate, ethyl 5-amino-1-(α-cyano-α-ethoxycarbonylmethyl)imidazole-4-carboxylate or diethyl 2-ethoxymethylidenamino-3H-imidazo[1,5-a]imidazole-3,7-dicarboxylate.

Mass spectral, n.m.r., i.r. and other analytical evidence is presented to support the structures assigned and the mechanisms of formation of the different compounds are discussed.