Synthesis and quaternization of 5-amino-1-aryl-imidazol-4carboxamides and their related imidazo-pyrazines

ABSTRACT

Because many amino-imidazoles and some quaternary imidazo lium salts are reported to possess numerous useful biological activities also due to the potential value of many pyrazines as intermediates in the synthesis of the biologically important petridines; the synthesis and quaternization of some new 4 [5]-amino-imidazole-5 [4]-carboxamides and their related imidazo-pyrazines, in the present work, is therefore attempted. Thus, it is found that l-aryl-5-ami no-imidazole-4-carboxamides 3a-d are smoothly obtained, in situ, by a facil ring closure of N-[aryl-formimidate [1] when heated under reflux, in acetonitrile, with 2-amino-2-cyanoacetamide. Meanwhile, compounds 3 are also obtained from the reaction of methyl-N-[carbamoylcyanomethyl]-formimidate [2] with the desired aromatic amine; in the same solvent [Undepressed mixed m.ps.]