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Synlett 2001; 2001(8): 1317-1319
DOI: 10.1055/s-2001-16071
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Improve Method for Synthesis of 4-Thioaryl-2,3,4-trihydro-1-benzothiopyrans: Acid-induced Stereoselective Intermolecular Cycloaddition of α,β-Unsaturated Aldehydes with Arenethiols

Yoshio Ishino* , Masatoshi Mihara, Hidehito Kawai
  • *Osaka Municipal Technical Research Institute 1-6-50, Morinomiya, Joto-ku, Osaka 536-8553, Japan; Fax + 81-6-69 63-80 51; E-mail: ishino@omtri.city.osaka.jp
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Publication Date:
31 December 2001 (online)

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A catalytic amount of acids catalyzed reaction of α,β-unsaturated aldehydes with arenethiols in 1,2-dichloroethane brought about intermolecular cycloaddition to give the corresponding 4-thioaryl-2,3,4-trihydro-1-benzothiopyrans (thiochromans) in good to excellent yield. These reactions are assumed to proceed through allylic cationic intermediates generated in site.

benzothiopyrans - acids catalysts - unsaturated aldehydes - arenethiols - intermolecular cycloaddition