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Paper | Regular issue | Vol 36, No. 10, 1993, pp.2383-2396
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6476
The Novel Reduction of Pyridine Derivatives with Samarium Diiodide

Yasuko Kamochi* and Tadahiro Kudo

*Daiichi College of Pharmaceutical Sciences, 22-1 Tamagawa-cho, Minami-ku, Fukuoka 815-0037, Japan

Abstract

Pyridine was rapidly reduced into piperidine with samarium diiodide in the presence of water at toom temperature in excellent yield. On the similar reactions of pyridine derivatives bearing chloro, amino and cyano functionalities with samarium diiodide-H2O-THF system, these functionalities were partly eliminated with this system to afford pyridine or piperidine. Furthermore, pyridinecarboxamides were reduced with this system to give the corresponding methylpyridines and 2-pyridinecarboxylic acid was reduced to give 2-methylpyridine as the major products.