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Short Paper | Regular issue | Vol 96, No. 5, 2018, pp.902-909
Published online, 12th April, 2018
DOI: 10.3987/COM-18-13882
One-Pot Synthesis of 2-Substituted 1H-Isoindole-1,3(2H)-dithiones from Secondary Benzothioamides and Isothiocyanates

Kazuhiro Kobayashi,* Daiki Fujiwara, and Miyuki Tanmatsu

*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


The reaction of 2,N-dilithiobenzothioamides, generated from readily available secondary benzothioamides and two equivalents of butyllithium, with isothiocyanates, followed by aqueous workup, gives the corresponding N1,N2-disubstituted benzene-1,2-dicarbothioamides, which undergo intramolecular attack of one of the thioamide nitrogen on the adjacent thiocarbonyl moiety with loss of primary amines to provide 2-substituted 1H-isoindole-1,3(2H)-dithiones.