N. Cusack, G. Shaw, F. I. Logemann
1980
Citations
0
Influential Citations
8
Citations
Journal
Journal of The Chemical Society-perkin Transactions 1
Abstract
Ethyl and benzyl 5-amino-1-(2-pyridyl)imidazole-4-carboxylates, obtained from ethyl or benzyl α-amino-α-cyanoacetate, respectively, and ethyl formimidate hydrochloride followed by 2-aminopyridine, were converted into 5-amino-1-(2-pyridyl)-imidazole-4-carboxylic acid which was decarboxylated in situ to 5-amino-1-(2-pyridyl)imidazole. Reaction of 2-N-formylamino-N-(2-pyridyl)acetamide with ammonia and ammonium chloride gave 5-aminoimidazole and a similar reaction with the nucleotide 2-N-formylglycineamide ribotide similarly gave evidence for aminoimidazole formation. 4-Cyano-5-imidazolone, prepared by reaction of 2-cyano-N-formylacetamide with nitrous acid and reduction of the hydroxyimino derivative so produced, with ammonia and ammonium sulphite at 100 °C, gave 5-aminoimidazole-4-carboxamide. Implications of the reactions involved are discussed.