Oxidation of aminoalkyl and hydroxylaminoalkyl furans
TETRAHEDRON LETTERS, cilt.56, sa.50, ss.6994-6997, 2015 (SCI-Expanded, Scopus)
- 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
- Anahtar Kelimeler: Aminoalkylfuran, Hydroxylaminofuran, Oxidation, Substituted pyrrolidine, Substituted isooxazoline
- 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.