An efficient one-step regiospecific synthesis of novel isoxazolines and isoxazoles of N-substituted saccharin derivatives through solvent-free microwave-assisted [3+2] cycloaddition

Novel isoxazolines and isoxazoles of N-substituted saccharin derivatives are synthesized in good yields by 1,3-dipolar cycloaddition of N-allyl or propargyl N-substituted saccharin with arylnitrile oxide under solvent-free microwave irradiation. In this process, the yields were significantly improve...

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Bibliographic Details
Published inTetrahedron letters Vol. 48; no. 3; pp. 443 - 447
Main Authors Mabrour, Mahmoud, Bougrin, Khalid, Benhida, Rachid, Loupy, André, Soufiaoui, Mohamed
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 15.01.2007
Elsevier
Subjects
1,3-Dipolar cycloaddition
Arylnitrile oxide
Chemistry
Chemistry, Organic
Microwave activation
Physical Sciences
Regiocontrolled process
Saccharin analogs
Science & Technology
Microwave activation
1,3-Dipolar cycloaddition
Regiocontrolled process
Saccharin analogs
Arylnitrile oxide
regio-controlled process
REAGENT
ROUTE
microwave activation
IN-VITRO EVALUATION
ELASTASE
CHEMISTRY
arylnitrile oxide
NITRILE OXIDE CYCLOADDITIONS
CYCLIZATION
1,3-dipolar cycloaddition
saccharin analogs
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Summary:Novel isoxazolines and isoxazoles of N-substituted saccharin derivatives are synthesized in good yields by 1,3-dipolar cycloaddition of N-allyl or propargyl N-substituted saccharin with arylnitrile oxide under solvent-free microwave irradiation. In this process, the yields were significantly improved over conventional heating, without alteration of the selectivity. The regioselectivity as well as the nonthermal specific microwave effect are discussed.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2006.11.067