Studies on quinoline and isoquinoline derivatives. IV. Reaction of quinoline and isoquinoline N-oxides with 3-aminocrotononitrile and related compounds.

The reaction of quinoline 1-oxide with 3-aminocrotononitrile or 3-aminocinnamonitrile in the presence of benzoyl chloride afforded 2-methyl-or 2-phenyl-imidazo [1, 2-a] quinoline-1-carbonitriles along with the 2-substituted quinoline derivatives. This reaction was also observed on isoquinoline 2-oxide and 1-methyl- and 1-phenyl-imidazo [2, 1-a] isoquinoline-2-carbonitriles were obtained. The mechanism of the reaction was described tentatively.