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Short Paper | Regular issue | Vol 96, No. 9, 2018, pp.1610-1621
Published online, 26th July, 2018
DOI: 10.3987/COM-18-13946
Synthesis of 3-Hydroxy-2,3-dihydro-1H-isoindole-1-thione Derivatives by the Reaction of 2,N-Dilithiobenzamides with Carboxylic Esters

Kazuhiro Kobayashi,* Daiki Fujiwara, Kazuma Nozaki, and Takashi Nogi

*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

An efficient one-pot method for the preparation of 2,3-disubstituted 3-hydroxy-2,3-dihydro-1H-isoindole-1-thiones from secondary benzothioamides and carboxylic esters has been developed. Thus, the reaction of the starting thioamides with two equivalents of butyllithium generates the corresponding 2,N-dilithiobenzothioamides, which are then allowed to react with carboxylic esters to give the desired products. The similar preparation of 4- and 5-aza-analogues from 2(or 3)-bromopyridine-3(or 4)-carbothioamides, respectively, is also described.