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Short Paper | Regular issue | Vol 96, No. 8, 2018, pp.1430-1440
Published online, 4th July, 2018
DOI: 10.3987/COM-18-13933
A Facile Synthesis of 4-Aryl-1H-2-benzothiopyran-3-carboxylic Acid Derivatives from o-Bromobenzyl Mercaptans

Kazuhiro Kobayashi,* Syunta Furugaki, and Takuma Ueyama

*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

The synthesis of 4-aryl-1H-2-benzothiopyran-3-carboxylic acid derivatives by a sodium hydride-mediated thiopyran ring formation of 2-[(2-aroylphenyl)methylsulfanyl]acetic acid derivatives is reported. The precursors were prepared by successive treatment of lithium o-lithiobenzyl mercaptides, which were generated by the reaction of o-bromobenzyl mercaptans with two equivalents of butyllithium, with aromatic aldehydes and 2-bromoacetonitrile or tert-butyl 2-bromoacetate, followed by oxidation of the resulting sulfanyl alcohols with pyridinium chlorochromate (PCC).