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Short Paper | Regular issue | Vol 94, No. 9, 2017, pp.1759-1765
Published online, 28th July, 2017
DOI: 10.3987/COM-17-13756
One-Pot Synthesis of 2-Substututed 3-Thioxo-2,3-dihydro-1H-isoindol-1-ones by the Reaction of N-Substituted 2,N-Dilithiobenzamides with Isothiocyanates

Kazuhiro Kobayashi* and Daiki Fujiwara

*Applied Chemistry Field, Chemistry and Biotechnology Course, Department of Engineering, Graduate School of Sustainability Science, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan

Abstract

This paper describes an efficient one-pot method for the preparation of 2-substituted 3-thioxo-1H-isoindol-1-ones (3-thioxoisoindolinones) by the reaction of N-substituted 2,N-dilithiobenzamides, generated by treating N-substituted benzamides with two equivalents of butyllithium, with the respective isothiocyanates followed by ring closure of the resulting N-alkyl(or aryl)-2-(alkyl(or aryl)thiocarbamoyl)benzamide derivatives with loss of alkyl(or aryl)amines.