Tricyclic-isoxazolidine analogues via intramolecular 1,3-dipolar cycloaddition reactions of nitrones |
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| Authors: | Simon Saubern James M. Macdonald Ruth C.J. Woodgate Matthew J. Fuchter Jonathan M. White |
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| Affiliation: | a CSIRO Molecular and Health Technologies, Bag 10, Clayton South, VIC 3169, Australia
b School of Chemistry, Bio21 Institute, University of Melbourne, Parkville, VIC 3010, Australia |
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| Abstract: | The tricyclic-isoxazolidine analogues tetrahydrothiochromenoisoxazoles, hexahydroisoxazolequinolines and tetrahydroisoxazolepyranopyridines were prepared by an intramolecular 1,3-dipolar cycloaddition reaction of a nitrone with an alkene. For N-alkylated hexahydroisoxazolequinolines, reduction of the reaction time from two days to 40 min was achieved using microwave heating. The cyclization to form tetrahydroisoxazolepyranopyridines only proceeded when the alkene was substituted with an electron withdrawing group. |
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| Keywords: | 1,3-Dipolar cycloaddition Nitrones Isoxazoles |
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