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Synthesis 1989; 1989(1): 20-24
DOI: 10.1055/s-1989-27133
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Regioselective Synthesis of 5-Alkylthio- and 3-Alkylthioisoxazoles from Acylketene Dithioacetals

M. L. Purkayastha* , H. Ila, H. Junjappa
  • *Department of Chemistry, North-Eastern Hill University, Shillong 793003, Meghalaya, India
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Publication Date:
27 September 2002 (online)

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A regioselective synthesis of isomeric 5-alkylthio- and 3-alkylthioisoxazoles 3 and 4 has been developed from acylketene dithioacetals 2. Thus the reaction of 2a-l with hydroxylamine hydrochloride in the presence of sodium methoxide in refluxing methanol afforded 3-substituted 5-alkylthioisoxazoles 3a-l in good yields. When compounds 2a-l were reacted with hydroxylamine hydrochloride in the presence of sodium acetate/acetic acid (pH 2.2) in refluxing ethanol/benzene, 3-alkylthioisoxazoles 4a-l were obtained regioselectively in good yields. Mass-spectral fragmentation and the mechanism of the formation of 3 and 4 are discussed.

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