Journal of the Chemical Society. Perkin transactions I p. 2316 - 2321 (1980)
Update date:2022-08-05
Topics:
Cusack, Noel J.
Shaw, Gordon
Logemann, Fatma I.
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-formylglicineamide 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 deg C, gave 5-aminoimidazole-4-carboxamide.Implications of the reactions involved are discussed.
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Doi:10.1007/BF00561343
(1980)Doi:10.1021/ja00766a016
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