Rearrangement of 4‑Amino-3-halo-pyridines by Nucleophilic Aromatic Substitution

The reaction of 3-halo-4-aminopyridines with acyl chlorides and triethylamine is described. The pyridin-4-yl α-substituted acetamide products were obtained in moderate to high yields. The presented rearrangement reaction, in which the presumed N-acylated intermediate reacts intramolecularly via nucl...

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Bibliographic Details
Published in:	Journal of organic chemistry Vol. 78; no. 11; pp. 5705 - 5710
Main Authors:	Getlik, Matthäus, Wilson, Brian J, Morshed, M. Monzur, Watson, Iain D. G, Tang, Doris, Subramanian, Pandiaraju, Al-awar, Rima
Format:	Journal Article
Language:	English
Published:	United States American Chemical Society 07-06-2013
Subjects:	Acetamides - chemical synthesis Acetamides - chemistry Crystallography, X-Ray Ethylamines - chemistry Hydrocarbons, Chlorinated - chemistry Models, Molecular Molecular Structure Pyridines - chemistry
Online Access:	Get full text
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Summary:	The reaction of 3-halo-4-aminopyridines with acyl chlorides and triethylamine is described. The pyridin-4-yl α-substituted acetamide products were obtained in moderate to high yields. The presented rearrangement reaction, in which the presumed N-acylated intermediate reacts intramolecularly via nucleophilic aromatic substitution, results in a formal two-carbon insertion.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo4003773