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Paper | Regular issue | Vol 31, No. 5, 1990, pp.895-909
Published online, 1st January, 1970
DOI: 10.3987/COM-90-5369
Reaction of Methoxy-N-heteroarmatics with Phenylacetonitrile under Basic Conditions

Hiroshi Yamanaka* and Setsuya Ohba

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan

Abstract

The monomethoxyl derivatives of various π-elelctron-deficient N-heteroaromatics with phenylacetonitrile in tetrahydrofuran in the presence of sodium hydride to give α-phenyl-N-heteroareneacetonitriles in the yields ranging from 45 to 78%. On the contrary, the reaction of these methoxyl derivatives wit ethyl cyanoacetate or malononitrile under similar conditions was restricted within narrow limits. The synthesis of benzoyl-N-heteroaromatics by the air-oxidation of α-phenyl-N-heteroareneacetonitriles was described additionally.