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Short Paper | Regular issue | Vol 85, No. 8, 2012, pp.1997-2004
Published online, 8th June, 2012
DOI: 10.3987/COM-12-12508
A Convenient Synthesis of 2-Arylthiochromen-4-ones (Thioflavones) by Iodine-Mediated Cyclization of 3-Aryl-1-[2-(1,1-dimethylethylsulfanyl)phenyl]prop-2-en-1-ones

Kazuhiro Kobayashi,* Akihiro Kobayashi, and Kosuke Ezaki

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

Abstract

A convenient two-step synthesis of 2-arylthiochromen-4-ones (thioflavones) beginning with 1-[2-(1,1-dimethylethylsulfanyl)phenyl]ethanones is described. Thus, 3-aryl-1-[2-(1,1-dimethylethylsulfanyl)phenyl]prop-2-en-1-ones were prepared by the condensation of 1-[2-(1,1- dimethylethylsulfanyl)phenyl]ethanones with aromatic aldehyde in the presence of sodium hydroxide, and were treated with iodine in refluxing N-methylpyrrolidin-2-one (NMP) or propanenitrile to afford the desired products in moderate to fair yields.