Oxidation of aminoalkyl and hydroxylaminoalkyl furans

KAZANCIOGLU M. Z., KAZANCIOGLU E. A., SEÇEN H., Altundas R.

TETRAHEDRON LETTERS, cilt.56, sa.50, ss.6994-6997, 2015 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 56 Sayı: 50
  • Basım Tarihi: 2015
  • Doi Numarası: 10.1016/j.tetlet.2015.10.105
  • Dergi Adı: TETRAHEDRON LETTERS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.6994-6997
  • Atatürk Üniversitesi Adresli: Evet

Özet

The oxidation reactions of amino and hydroxylamino substituted alkylfurans were explored for the synthesis of structurally complex compounds from simple starting materials. A novel photooxygenation of the furan derivatives gave an alpha,beta-unsaturated dicarbonyl moiety which underwent subsequent conjugate addition to yield diastereomeric mixtures of the corresponding pyrrolidine and isoxazoline heterocycles. Oxidation of the alpha,beta-unsaturated dicarbonyl using mCPBA gave epoxide intermediates, which were opened by nucleophilic attack of the amino groups, furnishing pyrrolidine and isoxazolidine heterocycles. (C) 2015 Elsevier Ltd. All rights reserved.