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Oxidation of aminoalkyl and hydroxylaminoalkyl furans

Author:
Kazancioglu, Mustafa Zahrittin, Akin Kazancioglu, Elif, Secen, Hasan, Altundas, Ramazan
Source:
Tetrahedron letters 2015 v.56 no.50 pp. 6994-6997
ISSN:
0040-4039
Subject:
Lewis bases, furans, moieties, oxidation
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 mCPBA gave epoxide intermediates, which were opened by nucleophilic attack of the amino groups, furnishing pyrrolidine and isoxazolidine heterocycles.
Agid:
6040621