Acid-Catalyzed 1,3-Dipolar Cycloaddition of 2H‑Azirines with Nitrones: An Unexpected Access to 1,2,4,5-Tetrasubstituted Imidazoles

The first 1,3-dipolar cycloaddition of 2H-azirines with nitrones, a straightforward approach toward the regioselective synthesis of 1,2,4,5-tetrasubstituted imidazoles, is reported. This trifluoroacetic acid-catalyzed protocol tolerates a broad range of aliphatic and aromatic substrates, offering an...

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Published inJournal of organic chemistry Vol. 85; no. 5; pp. 3587 - 3595
Main Authors Angyal, Anikó, Demjén, András, Wölfling, János, Puskás, László G, Kanizsai, Iván
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.03.2020
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
REARRANGEMENT
APOPTOSIS
ENANTIOSELECTIVE SYNTHESIS
VINYL AZIDES
CHEMISTRY
REACTIVITY
SELECTIVE SYNTHESIS
INHIBITORS
PYRIDINES
PYRAZINES
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Summary:The first 1,3-dipolar cycloaddition of 2H-azirines with nitrones, a straightforward approach toward the regioselective synthesis of 1,2,4,5-tetrasubstituted imidazoles, is reported. This trifluoroacetic acid-catalyzed protocol tolerates a broad range of aliphatic and aromatic substrates, offering an efficient access to highly diverse, multisubstituted imidazoles in isolated yields up to 83% under mild conditions.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b03288