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Paper | Regular issue | Vol 34, No. 2, 1992, pp.357-362
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5931
Amidoalkylation of Pyrazine-2,3-dicarbonitrile by the Radical Generated from N-Alkanoylanilinoalkanoic Acid

Masaru Tada,* Reiko Furuse, and Hiroko Kashima

*Department of Chemistry, School of Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo 169, Japan

Abstract

N-Alkanoylanilinoacetic acid and 2-N-alkanoylanilinopropionic acid gave N-alkanoylanilinomethyl radical and 1-N-alkanoylanilinoethyl radical respectively by the peroxodisulfate oxidation catalized by silver ion. The former radical reacts with pyrazine-2,3-dicarbonitrile to give both monosubstitution product (6) and disubstitution product (7), whereas the latter radical gives only monosubstitution product due to the steric hindrance for the second radical substitution.