TETRAHEDRON, vol.70, no.4, pp.817-831, 2014 (SCI-Expanded)
Article / Article
Science Citation Index Expanded (SCI-EXPANDED), Scopus
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:
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.