Bulletin of the Chemical Society of Japan p. 2046 - 2049 (1980)
Update date:2022-08-04
Topics:
Nakazumi, Hiroyuki
Asada, Akira
Kitao, Teijiro
The products formed by the reaction of benzenethiols with diketene in the presence of H2SO4 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 prepare 2H-1-benzothiopyran-2-ones (thiocoumarins).It is found that 4-methyl(thiocoumarins) were conveniently prepared by thereaction of 1 with anhydrous aluminium chloride in yields of 16-48percent.When 1 was treated with PPA, isomeric 2-methyl(thiochromones) were preferentially obtained in yields of 5-66percent, and compound 2 was isolated as an intermediate.The spectral characteristics of 4-methyl(thiocoumarins) have also been described.
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Doi:10.1021/ol052214x
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(1980)