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Domino Knoevenagel Condensation/Aza‐Ene Addition/ N ‐Cyclization Route to Functionalized Imidazo[1,2‐ a ]pyridines and Pyrido[1,2‐ a ]pyrimidines
Author(s) -
Sivakumar Sathiyamoorthi,
Kumar Raju Ranjith
Publication year - 2014
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201402100
Subject(s) - chemistry , knoevenagel condensation , acetonitriles , domino , tautomer , enamine , imine , organic chemistry , cascade reaction , condensation reaction , combinatorial chemistry , medicinal chemistry , catalysis , acetonitrile
A highly efficient and facile route to imidazo[1,2‐ a ]pyridines and pyrido[1,2‐ a ]pyrimidines is described by using the three‐component reaction of aroyl acetonitriles, nitroketene aminals, and either isatins or aromatic aldehydes in the presence of Et 3 N. This one‐pot strategy occurs in a single step and involves a domino Knoevenagel condensation/aza‐ene addition/imine–enamine tautomerization/chemoselective N ‐cyclization sequence of reactions to afford the products in excellent yields without the need for purification by column chromatography.