Synthesis of Imidazo[1,2‑a]pyridines: “Water-Mediated” Hydroamination and Silver-Catalyzed Aminooxygenation

Aqueous syntheses of methylimidazo[1,2-a]pyridines without any deliberate addition of catalyst are reported. Imidazo[1,2-a]pyrazine and imidazo[2,1-a]isoquinoline were also obtained in good yields under similar conditions. With acetonitrile as solvent, Ag-catalyzed intramolecular aminooxygenation pr...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 78; no. 3; pp. 1266 - 1272
Main Authors Chandra Mohan, Darapaneni, Nageswara Rao, Sadu, Adimurthy, Subbarayappa
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.02.2013
Amer Chemical Soc
Subjects
acetonitrile
Catalysis
catalysts
Chemistry
Chemistry, Organic
Imidazoles - chemical synthesis
Imidazoles - chemistry
Isoquinolines - chemical synthesis
Isoquinolines - chemistry
organic chemistry
Physical Sciences
Pyrazines - chemical synthesis
Pyrazines - chemistry
pyridines
Pyridines - chemical synthesis
Pyridines - chemistry
Science & Technology
Silver - chemistry
solvents
Structure-Activity Relationship
Water
ALKENES
ZOLPIDEM
ONE-POT SYNTHESIS
AMINES
ALPIDEM
ALKYNES
DERIVATIVES
AMINOPYRIDINES
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Summary:Aqueous syntheses of methylimidazo[1,2-a]pyridines without any deliberate addition of catalyst are reported. Imidazo[1,2-a]pyrazine and imidazo[2,1-a]isoquinoline were also obtained in good yields under similar conditions. With acetonitrile as solvent, Ag-catalyzed intramolecular aminooxygenation produced imidazo[1,2-a]pyridine-3-carb­aldehydes in moderate to good yields.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/jo3025303