Oxidation of aminoalkyl and hydroxylaminoalkyl furans. Issue 50 (16th December 2015)

• Record Type: Journal Article
• Authors: Kazancioglu, Mustafa Zahrittin; Akin Kazancioglu, Elif; Secen, Hasan; Altundas, Ramazan
• Is Part Of: Tetrahedron letters. Volume 56:Issue 50(2015)
• Page Start: 6994
• Page End: 6997
• Publication Date: 2015-12-16
• Subjects: Aminoalkylfuran -- Hydroxylaminofuran -- Oxidation -- Substituted pyrrolidine -- Substituted isooxazoline; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.10.105
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: 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 α, β-unsaturated dicarbonyl moiety which underwent subsequent conjugate addition to yield diastereomeric mixtures of the corresponding pyrrolidine and isoxazoline heterocycles. Oxidation of the α, β-unsaturated dicarbonyl using m CPBA gave epoxide intermediates, which were opened by nucleophilic attack of the amino groups, furnishing pyrrolidine and isoxazolidine heterocycles.