Electrochemically Induced Synthesis of Imidazoles from Vinyl Azides and Benzyl Amines

An electrochemically induced synthesis of imidazoles from vinyl azides and benzyl amines was developed. A wide range of imidazoles were obtained, with yields of 30 to 64%. The discovered transformation is a multistep process whose main steps include the generation of electrophilic iodine species, 2H...

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Published inMolecules (Basel, Switzerland) Vol. 27; no. 22; p. 7721
Main Authors Vil’, Vera A., Grishin, Sergei S., Terent’ev, Alexander O.
Format Journal Article
LanguageEnglish
Published Switzerland MDPI AG 01.11.2022
MDPI
Subjects
Amines
Antifungal agents
Azide
Azides - chemistry
Catalysis
Cyclization
electrochemistry
Hydrocarbons
imidazoles
Imidazoles - chemistry
Iodine
Organic chemistry
Oxidation
vinyl azides
electrochemistry
imidazoles
vinyl azides
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Summary:An electrochemically induced synthesis of imidazoles from vinyl azides and benzyl amines was developed. A wide range of imidazoles were obtained, with yields of 30 to 64%. The discovered transformation is a multistep process whose main steps include the generation of electrophilic iodine species, 2H-azirine formation from the vinyl azide, followed by its reactions with benzyl amine and with imine generated from benzyl amine. The cyclization and aromatization of the obtained intermediate lead to the target imidazole. The synthesis proceeds under constant current conditions in an undivided cell. Despite possible cathodic reduction of various unsaturated intermediates with C=N bonds, the efficient electrochemically induced synthesis of imidazoles was carried out.
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ISSN:1420-3049
1420-3049
DOI:10.3390/molecules27227721