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Type: Artigo de periódico
Title: Synthesis of new aza-bicyclic 2-isoxazolines by 1,3-dipolar cycloaddition of endocyclic enecarbamates and enamides with nitrile oxides
Author: de Almeida, VM
dos Santos, RJ
Goes, AJD
de Lima, JL
Correia, CRD
de Faria, AR
Abstract: Novel aza-bicyclic 2-isoxazolines, 4,5-dihydroisoxazole[5,4-b]pyrrolidines, and 4,5-dihydroisoxazole[5,4b]piperidines were synthesized in a highly regioselective manner through a 1,3-dipolar cycloaddition reaction of 5- and 6-membered endocyclic enecarbamates and enamides with several nitrile oxides in good to excellent yields. Hydrogenolysis of 5- and 6-membered Cbz-cycloadducts led to secondary amines, which presented distinctive stabilities. 2-Isoxazoline bisamides were obtained in good yields through a N-benzoylation, followed by ammonolysis of the secondary amine, or directly from ammonolysis of the cycloadducts. (C) 2008 Elsevier Ltd. All rights reserved.
Subject: Endocyclic enecarbamates
1,3-Dipolar cycloaddition
Nitrile oxides
Country: Inglaterra
Editor: Pergamon-elsevier Science Ltd
Citation: Tetrahedron Letters. Pergamon-elsevier Science Ltd, v. 50, n. 6, n. 684, n. 687, 2009.
Rights: fechado
Identifier DOI: 10.1016/j.tetlet.2008.11.096
Date Issue: 2009
Appears in Collections:Unicamp - Artigos e Outros Documentos

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