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Paper | Regular issue | Vol 87, No. 12, 2013, pp.2577-2587
Published online, 6th November, 2013
DOI: 10.3987/COM-13-12855
A Convenient Synthesis of 9H-Thioxanthen-9-ones and Their Aza-Analogues

Kazuhiro Kobayashi,* Toshihide Komatsu, Kazuhiro Nakagawa, Erika Hara, and Shohei Yuba

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

Abstract

An efficient method for the preparation of 9H-thioxanthen-9-ones and their three aza-analogues has been developed. The reaction of (2-fluorophenyl)(2-halophenyl)methanones, derived from 1-bromo-2-fluorobenzens and 2-halobenzaldehydes by an easy two-step sequence, with Na2S·9H2O in DMF at 60 °C gives 9H-thioxanthen-9-ones. This procedure can be applied to the synthesis of 5H-[1]benzothiopyrano[2,3-b](or [2,3-c])pyridin-5-ones or 10H-[1]benzothiopyrano[3,2-c]pyridin-10-ones starting from 2-, 3- or 4-chloropyridines, respectively.