Synthesis of the substituted 7H-pyrano[2,3-d]isoxazol-7-ones from allomaltol-containing oximes

Convenient approach for the synthesis of previously unknown 7H-pyrano[2,3-d]isoxazol-7-one core was elaborated. The presented method is based on two stage process including preparation of diketone monoximes and their subsequent intramolecular dehydration. It was shown that among various dehydrating...

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Bibliographic Details
Published inSynthetic communications Vol. 53; no. 24; pp. 2108 - 2116
Main Authors Milyutin, Constantine V., Komogortsev, Andrey N., Melekhina, Valeriya G., Lichitsky, Boris V.
Format Journal Article
LanguageEnglish
Published PHILADELPHIA Taylor & Francis 17.12.2023
Taylor & Francis Ltd
Subjects
Chemistry
Chemistry, Organic
Column chromatography
Dehydration
Diketones
Oximes
Physical Sciences
Science & Technology
Synthesis
ACIDS
1,2-BENZISOXAZOLES
diketone monoxime
allomaltol
GENERATED NITRILE OXIDES
EFFICIENT SYNTHESIS
BENZISOXAZOLES
two-stage process
hydrazone
3+2 CYCLOADDITION
7H-pyrano[2,3-d]isoxazol-7-one
FACILE SYNTHESIS
INHIBITORS
DERIVATIVES
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Summary:Convenient approach for the synthesis of previously unknown 7H-pyrano[2,3-d]isoxazol-7-one core was elaborated. The presented method is based on two stage process including preparation of diketone monoximes and their subsequent intramolecular dehydration. It was shown that among various dehydrating agents the best results were achieved using system TsCl/Et3N. The advantages of the considered procedure are easily available starting compounds, simple experimental procedure and isolation of the final products, avoiding column chromatography.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397911.2023.2272208