An efficient preparation of new homoallylamines and α-aminonitriles bearing furyl and thienyl rings

New diverse N‐aryl‐N‐[1‐furyl(thienyl)but‐3‐enyl]amines (homoallylamines) or 2‐(N‐arylmethylamino)‐2‐furyl(thienyl)acetonitriles (α‐aminonitriles) were easily prepared in good to excellent yields by an indium‐mediated Barbier‐type reaction between N‐hetarylaldimines and allyl bromide in MeOH or a di...

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Bibliographic Details
Published in:Journal of heterocyclic chemistry 2008-05, Vol.45 (3), p.927-930
Main Authors: Méndez, Leonor Y. Vargas, Kouznetsov, Vladimir V.
Format: Article
Language:English
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Summary:New diverse N‐aryl‐N‐[1‐furyl(thienyl)but‐3‐enyl]amines (homoallylamines) or 2‐(N‐arylmethylamino)‐2‐furyl(thienyl)acetonitriles (α‐aminonitriles) were easily prepared in good to excellent yields by an indium‐mediated Barbier‐type reaction between N‐hetarylaldimines and allyl bromide in MeOH or a direct three component reaction between anilines, hetaryl aldehydes and trimethylsilyl cyanide in the presence of a catalytic amount of molecular iodine at room temperature, respectively. The entire set of amines was characterized by IR, 1H and 13C NMR spectroscopy.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.5570450344