The acid-mediated intramolecular 1,3-dipolar cycloaddition of derived 2-nitro-1,1-ethenediamines for the synthesis of novel fused bicyclic isoxazoles |
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Authors: | Lee W Page Matthew Bailey Paul J Beswick Simon Frydrych Robert J Gleave |
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Institution: | GlaxoSmithKline, New Frontiers Science Park, Third Avenue, Harlow, Essex CM19 5AW, UK |
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Abstract: | The discovery of a novel synthesis of new fused bicyclic isoxazoles, for example, N-methyl-3-phenyl-5,6-dihydro-4H-isoxazolo3,4-c]azepin-8-amine (2a), N-methyl-3-phenyl-4,5-dihydroisoxazolo3,4-c]pyridin-7-amine (2b) and N-methyl-3-phenyl-4H-pyrrolo3,4-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. |
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Keywords: | 1 3-Dipolar cycloaddition Nitrile oxide 2-Nitro-1 1-ethenediamine Fused bicyclic isoxazole 7-Ring fused isoxazole 6-Ring fused isoxazole |
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