129694-58-2Relevant academic research and scientific papers
Synthesis of 5-Amino-4-(cyanoformimidoyl)-1H-imidazole: a Reactive Intermediate for the Synthesis of 6-Carbamoyl-1,2-dihydropurines and 6-Carbamoylpurines
Alves, M. Jose,Booth, Brian L.,Proenc, M. Fernanda J. R. P.
, p. 1705 - 1712 (1990)
5-Amino-4-(cyanoformimidoyl)-1H-imidazole (3) has been prepared in good yield by the basecatalysed cyclisation of (Z)-N-(2-amino-1,2-dicyanovinyl)formamidine.Compound (3) reacts with ketones, R1COR2 to give 2,2-disubstituted-6-carbamoyl-1,2-dihydropurines as the major products, together with minor amounts of compounds believed to be novel 7-amino-1-carbamoyl-3,3-disubstituted 3H-imidazoimidazole derivatives, which have been isolated when R1= R2= Et, Bu, and PhCH2; when R1= R2= Ph the only product isolated is tentatively assigned the imidazoimidazole structure.In the reaction with acetylacetone the 1,2-dihydropurine intermediate is unstable and loses acetone to give 2-methyl-6-carbamoylpurine.The aldehydes RCHO also react readily with (3) at room temperature to give the corresponding 6-carbamoyl-1,2-dihydropurine derivatives, which can be isolated when R= Me or Et; these oxidise in solution to afford the corresponding 6-carbamoylpurines.
