Purines, pyrimidines, and imidazoles. Part XXXIV. Synthesis and some reactions of N(6)-(formylmethyl)adenine

Abstract

N-(6)-(Formylmethyl)adenine has been prepared by careful controlled acidic hydrolysis of N-(6)-(2,2-diethoxyethyl)adenine, and converted into several simple derivatives. More vigorous treatment of the aldehyde with acid gave 5-amino-4(imidazol-2-yl)imidazole, which was converted into imidazo[2,1-i]purine by treatment with diethoxymethyl acetate. The structures of these compounds have been confirmed by chemical and spectroscopic methods and the mechanism of their formation is discussed.