DMF as an amine source: iron-catalyzed cyclization of 2H-azirines to imidazoles

A novel method has been developed for the synthesis of 1-methyl4,5-diaryl-1H-imidazoles through Fe(II)-catalyzed cyclization of 2H-azirines and N,N-dimethylformamide (DMF) as an amine source. This transformation involves the cleavage of C-N and C=N double bonds and the construction of new C-N and C=...

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Bibliographic Details
Published inChemical communications (Cambridge, England) Vol. 60; no. 14; pp. 1904 - 1907
Main Authors Zhao, Mi-Na, Yang, Zi-Mo, Li, Lian-Qing
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 13.02.2024
Royal Society of Chemistry
Subjects
Chemistry
Chemistry, Multidisciplinary
Dimethylformamide
Imidazole
Iron
Physical Sciences
Science & Technology
Substrates
Synthesis
CHLORIDES
CYCLOADDITION
PYRROLES
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Summary:A novel method has been developed for the synthesis of 1-methyl4,5-diaryl-1H-imidazoles through Fe(II)-catalyzed cyclization of 2H-azirines and N,N-dimethylformamide (DMF) as an amine source. This transformation involves the cleavage of C-N and C=N double bonds and the construction of new C-N and C=N double bonds. The reaction has readily available starting materials, a wide range of substrates and mild reaction conditions. In addition, the reaction also facilitated the convenient synthesis of 1-methyl-2,4,5-triaryl1H-imidazoles.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1359-7345
1364-548X
1364-548X
DOI:10.1039/d3cc06147g