Copper-catalyzed four-component synthesis of imidazo[1,2-a]pyridines via sequential reductive amination, condensation, and cyclization

[Display omitted] •A four component has been used to synthesis imidazo[1,2-a]pyridines.•The mechanism relies on sequential reductive amination, condensation, and cyclization.•Sodium azide acts as an ammonia surrogate to primary amines in a copper-catalyzed reductive amination of aryl halides. A nove...

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Bibliographic Details
Published in:Tetrahedron letters 2017-01, Vol.58 (2), p.121-124
Main Authors: Allahabadi, Emad, Ebrahimi, Sina, Soheilizad, Mehdi, Khoshneviszadeh, Mehdi, Mahdavi, Mohammad
Format: Article
Language:English
Subjects:
2-Bromopyridine
Aldehyde
Copper-catalyzed
Imidazo[1,2-a]pyridine
Isocyanide
Reductive amination
Sodium azide
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Summary:[Display omitted] •A four component has been used to synthesis imidazo[1,2-a]pyridines.•The mechanism relies on sequential reductive amination, condensation, and cyclization.•Sodium azide acts as an ammonia surrogate to primary amines in a copper-catalyzed reductive amination of aryl halides. A novel and efficient four-component approach for the synthesis of 2,3-disubstituted imidazo[1,2-a]pyridines is described. The copper-catalyzed reductive amination of 2-bromopyridine by sodium azide followed by sequential condensation and cyclization with aldehydes and isocyanides afforded the corresponding imidazo[1,2-a]pyridines in good yields.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2016.11.081