Synthesis and DFT studies of novel aminoimidazodipyridines using 2-(3H-imidazo[ 4,5-b]pyrid-2-yl)acetonitrile as an efficient key precursor.

Novel 9-aminoimidazo[1,2-a:5,4-b']dipyridine-6,8-dicarbonitriles were prepared via the Michael addition reaction of readily accessible 2-(3H-imidazo[4,5-b]pyrid-2-yl)acetonitrile with arylidenemalononitriles. The regioselectivity of the reaction was supported by theoretical calculations at the DFT level. In contrast, the reaction of the appropriate bis-arylidenemalononitrile with 2-(3H-imidazo[4,5-b]pyrid-2-yl)acetonitrile under similar reaction conditions gave the corresponding bis[2-(3H-imidazo[4,5-b]pyrid-2-yl)acrylonitriles]. [ABSTRACT FROM AUTHOR]