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Vanadyl Acetylacetonate Catalyzed Methylenation of Imidazo[1,2‐ a ]pyridines by Using Dimethylacetamide as a Methylene Source: Direct Access to Bis(imidazo[1,2‐ a ]pyridin‐3‐yl)methanes
Author(s) -
Kaswan Pinku,
Nandwaitesh Kumar,
DeBoef Brenton,
Kumar Anil
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201600225
Subject(s) - chemistry , catalysis , methylene , iodobenzene , dimethylacetamide , medicinal chemistry , pyridine , iminium , combinatorial chemistry , organic chemistry , solvent
An efficient protocol has been developed for the methylenation of imidazo[1,2‐ a ]pyridines using dimethylacetamide (DMA) as methylene source in the presence of vanadyl acetylacetonate [VO(acac) 2 ] as the catalyst and iodobenzene diacetate as the oxidant. The reaction involves coupling of sp 3 ‐ and sp 2 ‐hybridized carbons and proceeds through the formation of an iminium ion. A wide variety of imidazo[1,2‐ a ]pyridines were converted to bis(imidazo[1,2‐ a ]pyridin‐3‐yl)methanes in good to excellent yields. A gram‐scale reaction demonstrated the potential for the scale‐up processes.