Amidinoacetamides in the synthesis of pyrimidines, imidazoles, and purines

Abstract

2-(Substituted amidino)acetamides and their 2-phenylazo-derivatives were cyclised with one-carbon-atom reagents to the corresponding pyrimidin-4(3H)-ones, identified by unambiguous synthesis from 4,6-dichloropyrimidine and by conversion into the corresponding 9-substituted hypoxanthines. The cyclisation of 2-(substituted amidino)-2-formamidoacetamide formate and hydrochloride salts to the isomeric ring and exocyclic N-substituted aminoimidazolecarboxamides was studied. The imidazolecarboxamides were converted, where possible, into the 3- or 9-substituted hypoxanthines.