Synthesis of 4,5-dihydroisoxazoles from N-nitroso-4,5-dihydropyrazoles under microwave activation

Substituted bicyclic and spirocyclic N-nitroso-4,5-dihydropyrazoles eliminate nitrogen under microwave irradiation within 3-8 minutes in solvent (chlorobenzene-DMF and chlorobenzene-AcOH) or in solvent-free conditions (on SiO2) to afford the corresponding 4,5-dihydroisoxazole derivatives. This metho...

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Bibliographic Details
Published inSynlett no. 8; pp. 1235 - 1238
Main Authors Stepakov, Alexander V., Galkin, Ivan A., Kostikov, Rafael R., Starova, Galina L., Starikova, Zoya A., Molchanov, Alexander P.
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 16.05.2007
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ROUTE
2-ISOXAZOLINES
OXIDE
dihydroisoxazoles
microwave activation
ISOXAZOLINE DERIVATIVES
N-nitrosodihydropyrazoles
NITROSYL CHLORIDE
FACILE
elimination
CYCLOPROPENE DERIVATIVES
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Summary:Substituted bicyclic and spirocyclic N-nitroso-4,5-dihydropyrazoles eliminate nitrogen under microwave irradiation within 3-8 minutes in solvent (chlorobenzene-DMF and chlorobenzene-AcOH) or in solvent-free conditions (on SiO2) to afford the corresponding 4,5-dihydroisoxazole derivatives. This methodology represents an improvement on thermolysis and allows 4,5-dihydroisoxazole systems to be obtained in good yields.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2007-977455