Additive-Free Three-Component Synthesis of Spiro-isoxazolidine-oxindoles Employing Trifluorodiazoethane

An efficient three-component protocol for the synthesis of trifluoromethylated spiro-isoxazolidine-oxindoles has been developed. This approach employs the 1,3-dipolar cycloaddition of trifluoromethyl nitrone, generated in situ from trifluorodiazoethane and nitrosoarene, with phenacylideneoxindoles....

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Published inJournal of organic chemistry Vol. 83; no. 23; pp. 14811 - 14819
Main Authors Gupta, Ekta, Nair, Sindoori R, Kant, Ruchir, Mohanan, Kishor
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.12.2018
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
NITRONE CYCLOADDITION
ASYMMETRIC-SYNTHESIS
RECEPTOR ANTAGONISTS
ANALOGS
1,3-DIPOLAR CYCLOADDITION
CF3CHN2
BETA-LACTAMS
ACCESS
2,2,2-TRIFLUORODIAZOETHANE
TRIFLUOROMETHYL DIAZOMETHANE
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Summary:An efficient three-component protocol for the synthesis of trifluoromethylated spiro-isoxazolidine-oxindoles has been developed. This approach employs the 1,3-dipolar cycloaddition of trifluoromethyl nitrone, generated in situ from trifluorodiazoethane and nitrosoarene, with phenacylideneoxindoles. A range of phenacyclideneoxindoles and nitrosoarenes can be subjected to this reaction to generate the spiro-isoxazolidine-oxindole derivatives. The reductive ring-opening reaction of isoxazolidines carried out to demonstrate the synthetic potential of our strategy resulted in an interesting rearrangement to yield pyrroloquinoline derivatives.
Bibliography:ObjectType-Article-1
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content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b02504