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Short Paper | Special issue | Vol 97, No. 1, 2018, pp.550-559
Published online, 2nd February, 2018
DOI: 10.3987/COM-17-S(T)13
One-Pot Synthesis of (Z)-N-Substituted Isobenzofuran-1(3H)-imines from Secondary Benzothioamides and Carbonyl Compounds

Kazuhiro Kobayashi* 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 methodology for the synthesis of (Z)-N-substituted isobenzofuran-1(3H)-imines starting from secondary benzothioamides has been developed. The reaction of the starting materials with two equivalents of butyllithium generated 2,N-dilithio-N-alkyl(or aryl)benzothioamides, which were then allowed to react with carbonyl compounds to give, after aqueous treatment, the desired products in satisfactory yields.