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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Bibliographic Details
Published inMonatshefte für Chemie Vol. 142; no. 9; pp. 917 - 921
Main Authors Mehrdad, Morteza, Faraji, Laleh, Jadidi, Khosrow, Eslami, Parisa, Sureni, Hossein
Format Journal Article
LanguageEnglish
Published Vienna Springer Vienna 01.09.2011
Springer Nature
Subjects
Analytical Chemistry
Chemistry
Chemistry and Materials Science
Chemistry, Multidisciplinary
Chemistry/Food Science
Inorganic Chemistry
Organic Chemistry
Original Paper
Physical Chemistry
Physical Sciences
Science & Technology
Theoretical and Computational Chemistry
Isatin ketonitrone
Ionic liquids
1,3-Dipolar cycloaddition
Spiro[oxindole-isoxazolidine] derivatives
ACIVICIN
NITRONES
(+)-NEGAMYCIN
CHEMISTRY
OXIDES
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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. Graphical abstract
ISSN:0026-9247
1434-4475
DOI:10.1007/s00706-011-0518-2