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

KIVRAK A., ZORA M.

TETRAHEDRON, cilt.70, sa.4, ss.817-831, 2014 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 70 Sayı: 4
  • Basım Tarihi: 2014
  • Doi Numarası: 10.1016/j.tet.2013.12.043
  • Dergi Adı: TETRAHEDRON
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.817-831
  • Anahtar Kelimeler: 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
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

Özet

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.