A novel synthesis of 1,2,4-oxadiazoles and isoxazoles

KIVRAK A., ZORA M.

TETRAHEDRON, vol.70, no.4, pp.817-831, 2014 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 70 Issue: 4
  • Publication Date: 2014
  • Doi Number: 10.1016/j.tet.2013.12.043
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.817-831
  • Keywords: 1,2,4-Oxadiazoles, Isoxazoles, Amidoximes, alpha,beta-Alkynic aldehydes, Conjugate addition, ONE-POT SYNTHESIS, SOLVENT-FREE CONDITIONS, ALPHA-AMINO-ACIDS, HIGHLY SUBSTITUTED ISOXAZOLES, TYROSINE KINASE ZAP-70, REGIOSELECTIVE SYNTHESIS, CONVENIENT SYNTHESIS, EFFICIENT SYNTHESIS, ELECTROPHILIC CYCLIZATION, TRISUBSTITUTED ISOXAZOLES
  • Middle East Technical University Affiliated: Yes

Abstract

A novel synthesis of 1,2,4-oxadiazoles and isoxazoles is described by utilizing the reactions between amidoximes and alpha,beta-alkynic aldehydes and/or ketones. Conjugate addition products, obtained from amidoximes and alpha,beta-alkynic aldehydes and/or ketones, afford 1,2,4-oxadiazoles and isoxazoles when treated with bases and acids, respectively. 1,2,4-Oxadiazoles can also be synthesized directly from amidoximes and alpha,beta-alkynic aldehydes in a one-pot manner under basic conditions. The reactions are general for a variety of starting compounds and tolerate the presence of aryl, heteroaryl and alkyl groups. (C) 2013 Elsevier Ltd. All rights reserved.