A regioselective and diastereoselective synthesis of new spiro-isoxazolidines via 1,3-dipolar cycloaddition of stable isatin ketonitrone and various dipolarophiles
The 1,3-dipolar cycloaddition of stable isatin ketonitrone with various dipolarophiles has been conducted under classical, ionic liquid, and solvent-free conditions to give novel spiro[oxindole-isoxazolidine] derivatives with similar diastereoselectivity. In the presence of the ionic liquid 1-butyl-...
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Published in | Monatshefte für Chemie Vol. 142; no. 9; pp. 917 - 921 |
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Main Authors | , , , , |
Format | Journal Article |
Language | English |
Published |
Vienna
Springer Vienna
01.09.2011
Springer Nature |
Subjects | |
Online Access | Get full text |
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Summary: | The 1,3-dipolar cycloaddition of stable isatin ketonitrone with various dipolarophiles has been conducted under classical, ionic liquid, and solvent-free conditions to give novel spiro[oxindole-isoxazolidine] derivatives with similar diastereoselectivity. In the presence of the ionic liquid 1-butyl-3-methylimidazolium bromide highly diastereoselective and regioselective cyclocondensation products were obtained in good to excellent yields in the absence of any catalyst. The reaction workup was simple and the ionic liquid was easily recovered from the reaction and reused.
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ISSN: | 0026-9247 1434-4475 |
DOI: | 10.1007/s00706-011-0518-2 |