Studies with functionally substituted enamines: synthesis of 2-aroyl-3-dimethylamino-2-propenenitrile and their reactivity toward nitrogen nucleophiles.

[摘要]：A facile and efficient synthesis of 2-substituted 3-dimethylamino-2-propenenitriles, RCOC(CN):CHNMe2 (I; R = 2-thienyl, 2-furyl, Ph) is described. Reaction of I with N2H4.H2O afforded 3-substituted 1H-4-pyrazolecarbonitriles. Compds. I reacted with 5-methyl-1H-pyrazol-3-amine to give 7-substituted pyrazolo[1,5-a]pyrimidine-6-carbonitriles and 2-substituted 5-aminopyrazolo[1,5-a]pyrimidine, and with 1H-benzo[d]imidazol-2-amine to give 3-substituted 2-aminobenzo[4,5]imidazo[1,2-a]pyrimidine and 4-substituted benzo[4,5]imidazo[1,2-a]pyrimidine 3-carbonitrile. The structures of compds. obtained were deduced based on 1H-NMR, HMBC-15N, and NOE difference expts.

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