A Mild Method for the Formation and in Situ Reaction of Imidoyl Chlorides:  Conversion of Pyridine-1-oxides to 2-Aminopyridine Amides

A mild, practical, one-pot method for the generation of imidoyl chlorides and their subsequent in situ reaction with pyridine-1-oxides is described. The imidoyl chlorides were formed from the reaction of secondary amides with a stoichiometric amount of oxalyl chloride and 2,6-lutidine in CH2Cl2 at 0...

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Bibliographic Details
Published in:Organic letters 2002-09, Vol.4 (18), p.3127-3129
Main Authors: Manley, Peter J, Bilodeau, Mark T
Format: Article
Language:English
Subjects:
Amides - chemical synthesis
Aminopyridines - chemical synthesis
Chemistry, Pharmaceutical - methods
Chlorides - chemistry
Oxalates - chemistry
Oxides - chemistry
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Summary:A mild, practical, one-pot method for the generation of imidoyl chlorides and their subsequent in situ reaction with pyridine-1-oxides is described. The imidoyl chlorides were formed from the reaction of secondary amides with a stoichiometric amount of oxalyl chloride and 2,6-lutidine in CH2Cl2 at 0 °C. Upon warming of the reaction mixture to room temperature in the presence of pyridine-1-oxides, a rapid conversion to 2-aminopyridine amides was observed in moderate to excellent isolated yields.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0264556