Tricyclic-isoxazolidine analogues via intramolecular 1,3-dipolar cycloaddition reactions of nitrones

S Saubern; JM Macdonald; JH Ryan; RCJ Woodgate; TS Louie; MJ Fuchter; JM White; AB Holmes

Journal article

Tricyclic-isoxazolidine analogues via intramolecular 1,3-dipolar cycloaddition reactions of nitrones

S Saubern, JM Macdonald, JH Ryan, RCJ Woodgate, TS Louie, MJ Fuchter, JM White, AB Holmes

Tetrahedron | PERGAMON-ELSEVIER SCIENCE LTD | Published : 2010

DOI: 10.1016/j.tet.2010.01.062

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. © 2010 Elsevier Ltd. All rights reserved.

University of Melbourne Researchers

Jonathan White Author

Andrew Holmes Author

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Funding Acknowledgements

We thank Dr R. Mulder for obtaining the valuable temperature 18 NMR spectra, Dr. A. Riches for useful suggestions and the Australian Research Council, the Commonwealth Scientific Industrial Research 19 Organisation and the Victorian Endowment for Science Knowledge and Innovation for generous financial support TS.L. was the thankful recipient of a CSIRO Summer student scholarship.