A Base Promoted Cyclization of N-Propargylaminopyridines. Synthesis of Imidazo[1,2-a]pyridine Derivatives

A base promoted cyclization of the protected N-propargylaminopyridines was shown to be an efficient method for the preparation of imidazo[1,2-a]pyridine derivatives. The reactions were carried out with a small excess of base, at room temperature or slightly above producing the heterocyclic products...

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Published inOrganic letters Vol. 13; no. 9; pp. 2286 - 2289
Main Authors Husinec, Suren, Markovic, Rade, Petkovic, Milos, Nasufovic, Veselin, Savic, Vladimir
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.05.2011
Amer Chemical Soc
Subjects
Amines - chemistry
Chemistry
Chemistry, Organic
Cyclization
Imidazoles - chemistry
Molecular Structure
Physical Sciences
Propane - chemistry
Pyridines - chemical synthesis
Pyridines - chemistry
Science & Technology
Stereoisomerism
KETONES
AMINATION
ACID
SOLID-PHASE SYNTHESIS
ONE-POT SYNTHESIS
ISOMERIZATION
ALDEHYDES
MULTICOMPONENT SYNTHESIS
SALTS
ALLENAMIDES
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Summary:A base promoted cyclization of the protected N-propargylaminopyridines was shown to be an efficient method for the preparation of imidazo[1,2-a]pyridine derivatives. The reactions were carried out with a small excess of base, at room temperature or slightly above producing the heterocyclic products in moderate to good yields. The stereoelectronic properties of substituents on the pyridine ring were shown to influence the cyclization process.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol200508x