Download PDF
Synthesis 1989; 1989(1): 20-24
DOI: 10.1055/s-1989-27133
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
27 September 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

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.