Syntheses of 2H-1-benzothiopyran-2-ones (thiocoumarins) and related compounds from benzenethiols and diketene

H Nakazumi, A Asada, T Kitao

Index: Nakazumi, Hiroyuki; Asada, Akira; Kitao, Teijiro Bulletin of the Chemical Society of Japan, 1980 , vol. 53, # 7 p. 2046 - 2049

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Citation Number: 14

Abstract

The products formed by the reaction of benzenethiols with diketene in the presence of H 2 SO 4 are (E)-β-(arylthio) crotonic acids (2) and/or isomeric (Z)-β-(arylthio) crotonic acids and not, as has been reported, S-phenyl 3-oxobutanethioates (1). Compounds 1a–k, as the precursor of thiocoumarins, were prepared from benzenethiols and diketene in the presence of triethylamine. The reaction of 1 with various condensing agents has been examined to ...