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Copper‐Based Metal–Organic Frameworks as Reusable Heterogeneous Catalysts for the One‐Pot Syntheses of Imidazo[1,2‐ a ]pyridines
Author(s) -
Puthiaraj Pillaiyar,
Ramu Andy,
Pitchumani Kasi
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.201402019
Subject(s) - chemistry , catalysis , intramolecular force , nitromethane , metal organic framework , reagent , heterogeneous catalysis , copper , intermolecular force , combinatorial chemistry , organic chemistry , molecule , adsorption
Abstract A copper terephthalate metal–organic framework (Cu(BDC) MOF, BDC=1,4‐benzenedicarboxylate) is used as a highly efficient heterogeneous catalyst for the one‐pot, atom‐economical synthesis of imidazo[1,2‐ a ]pyridines that proceeds through the three‐component coupling of aldehydes, aminopyridines, and nitromethane. This heterocyclic synthesis, which uses MOFs for the first time, involves an intermolecular aza‐Michael addition with a subsequent intramolecular cyclization and uses air as an environmentally benign oxidant. This heterogeneous Cu(BDC) MOF can be reused without the loss of its activity. Its catalytic efficiency was also highlighted by comparing it with other catalytic systems that have been used for the syntheses of imidazo[1,2‐ a ]pyridines. This procedure not only eliminates the use of environmentally hazardous reagents but also involves mild reaction conditions.