Interaction of α-chloroacetyl-2-azahetaryl acetonitriles with primary aliphatic amines

The reaction of α-chloroacetyl-2-azahetaryl acetonitriles with primary aliphatic amines has been studied. It has been shown that the interaction proceeds according to two pathways. Alkylation of the amino group with the subsequent addition of the N-H group to the cyano group yields 2-amino-4(5H)-ketopyrrols. Intramolecular alkylation affords pyrrolo[1,2-a]benzoazoles. The ratio of these two reaction routes has been found to depend on the basicity and structure of the starting compounds. The resulting compounds have been studied by IR and proton NMR spectroscopy and TLC.