Synthesis of Some Novel Heterocyclic Xylidinyl Amines and Carboxamides

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.