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Paper | Regular issue | Vol 75, No. 12, 2008, pp.3025-3033
Published online, 31st July, 2008
DOI: 10.3987/COM-08-11473
Synthesis of 1-Iminoisothiochroman Derivatives Based on Reactions of 2-Lithio-β-methoxystyrene Derivatives with Isothiocyanates Followed by Acid-mediated Cyclization

Kazuhiro Kobayashi,* Daisuke Nakai, Kazutaka Hayashi, and Hisatoshi Konishi

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

Abstract

The reaction of 2-lithio-β-methoxystyrene derivatives with isothiocyanates yields the corresponding 2-(2-methoxyvinyl)thiobenzamide derivatives. Treatment of these thiobenzamides with concentrated hydriodic acid affords 1-imino-3-methoxyisothiochroman (1-imino-3-methoxy-3,4-dihydro-1H- 2-benzothiopyran) derivatives.