Reaction of dianions of acyclic. beta.-enamino ketones with electrophiles. 3. Nitriles: synthesis of pyridine and pyrimidine derivatives

…, C Cimarelli, R Dalpozzo, G De Munno…

Index: Bartoli, Giuseppe; Bosco, Marcella; Cimarelli, Cristina; Dalpozzo, Renato; De Munno, Giovanni; et al. Journal of Organic Chemistry, 1992 , vol. 57, # 22 p. 6020 - 6025

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Citation Number: 23

Abstract

A new method for the construction of pyridine and pyrimidine derivatives is described, based on the electrophilic attack of nitriles to dianions of & (monoalkylamino)-a, &wturated ketones and the subsequent cyclization of the addition product. The reaction proceeds in good to high yields with both a'-and y-dianions which are regioselectively generated. The reaction of y-dianions with nitriles is strongly influenced by temperature. The y-addition produds ...