Studies on Isoxazoles. XIII. Synthesis and Chemical Properties of 3-Mercaptoisoxazoles

3-Mercaptoisoxazoles (XI) were synthesized from 3-allylsulfinylisoxazoles (II). The reaction of II with triphenylphosphine in the presence of acetic anhydride gave the corresponding 3-acetylthioisoxazoles (VII). The thioacetates (VII) were converted into 3-mercaptoisoxazoles (XI) by reaction with si...

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Bibliographic Details
Published inChemical & pharmaceutical bulletin Vol. 28; no. 2; pp. 552 - 557
Main Authors SUGAI, SOJI, TOMITA, KAZUO
Format Journal Article
LanguageEnglish
Published Tokyo The Pharmaceutical Society of Japan 1980
Japan Science and Technology Agency
Subjects
air oxidation
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Summary:3-Mercaptoisoxazoles (XI) were synthesized from 3-allylsulfinylisoxazoles (II). The reaction of II with triphenylphosphine in the presence of acetic anhydride gave the corresponding 3-acetylthioisoxazoles (VII). The thioacetates (VII) were converted into 3-mercaptoisoxazoles (XI) by reaction with silver nitrate and subsequent treatment of the resulting silver salts (X) with hydrogen sulfide. The thiols (XI) were oxidized in air to give the corresponding disulfides (XIV). In alkaline solution, 3-mercapto-5-phenylisoxazole (XIb) was decomposed into benzoylacetonitrile (IX) and sulfur.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.28.552