Synthesis of Some Novel Heterocyclic Xylidinyl Amines and Carboxamides

Abstract

The xylidines 1a, 1b undergo condensation with ethyl cyanoacetate 2 and ethyl benzoyl acetate 15 to afford the cyano acetanilides 3a, 3b and the β‐diketones 16a, 16b, respectively. Compounds 3a, 3b react with hydrazine and phenyl hydrazine to afford the azine‐bis derivatives 5a, 5b and 7a, 7b, whereas 16a, 16b react with the same reagents to afford the pyrazolyl amine derivatives 17a, 17b and 18a, 18b, respectively. Compounds 3a, 3b react also with dimethylformamide dimethylacetal to afford the enaminonitriles 8a, 8b, whereas 16a, 16b react with the same reagent to afford only the enaminone 19b. The enaminonitriles 8a, 8b react with hydrazine and phenyl hydrazine to afford also the azine‐bis derivatives 11a, 11b and 14a, 14b, respectively.