CHEMISTRY OF HCN .1. FORMATION AND REACTIONS OF N-(AMINOMETHYLIDENE)DIAMINOMALEONITRILE, AN HCN PENTAMER AND PRECURSOR TO ADENINE

N-(Aminomethylidene)diaminomaleonitrile (10) was shown to be a crucial and previously undetected intermediate in the formation of adenine (4) from diaminomaleonitrile (DAMN, 2) and formamidine acetate. Although stable in neutral 1-butanol at 100°C, 10 was selectively converted in alcohols with various reagents to any one of several products. Two of these products, 4-amino-5-cyanoimidazole (8) and 4-aminoimidazole-5-carboxamidine (11), appear to form by attack of the NH2CH= substituent at the adjacent nitrile. This mechanism is discussed relative to published proposals for the nonphotolytic prebiotic and preparative pathway(s) to adenine from DAMN or HCN. © 1979, American Chemical Society. All rights reserved.