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Synthesis of new aza-bicyclic 2-isoxazolines by 1,3-dipolar cycloaddition of endocyclic enecarbamates and enamides with nitrile oxides

✍ Scribed by Valderes Moraes de Almeida; Rosiel José dos Santos; Alexandre José da Silva Góes; José Gildo de Lima; Carlos Roque Duarte Correia; Antônio Rodolfo de Faria

Publisher
Elsevier Science
Year
2009
Tongue
French
Weight
272 KB
Volume
50
Category
Article
ISSN
0040-4039

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✦ Synopsis

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.

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