The acid-mediated intramolecular 1,3-dipolar cycloaddition of derived 2-nitro-1,1-ethenediamines for the synthesis of novel fused bicyclic isoxazoles

The discovery of a novel synthesis of new fused bicyclic isoxazoles, for example, N-methyl-3-phenyl-5,6-dihydro-4 H-isoxazolo[3,4- c]azepin-8-amine ( 2a), N-methyl-3-phenyl-4,5-dihydroisoxazolo[3,4- c]pyridin-7-amine ( 2b) and N-methyl-3-phenyl-4 H-pyrrolo[3,4- c]isoxazol-6-amine ( 2d) in high yield...

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Bibliographic Details
Published in:Tetrahedron letters 2010-06, Vol.51 (26), p.3388-3391
Main Authors: Page, Lee W., Bailey, Matthew, Beswick, Paul J., Frydrych, Simon, Gleave, Robert J.
Format: Article
Language:English
Subjects:
1,3-Dipolar cycloaddition
2-Nitro-1,1-ethenediamine
6-Ring fused isoxazole
7-Ring fused isoxazole
Fused bicyclic isoxazole
Nitrile oxide
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Summary:The discovery of a novel synthesis of new fused bicyclic isoxazoles, for example, N-methyl-3-phenyl-5,6-dihydro-4 H-isoxazolo[3,4- c]azepin-8-amine ( 2a), N-methyl-3-phenyl-4,5-dihydroisoxazolo[3,4- c]pyridin-7-amine ( 2b) and N-methyl-3-phenyl-4 H-pyrrolo[3,4- c]isoxazol-6-amine ( 2d) in high yield is reported. We speculate that the reaction proceeds via acid-mediated intramolecular 1,3-dipolar cycloaddition from 2-nitro-1,1-ethenediamines 1a, b, d.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2010.04.098