期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 355, 期 11-12, 页码 2263-2273出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201300157
关键词
aerobic oxidative cyclization; Cu-catalyzed reaction; diamination; haloalkynes; imidazopyridines
资金
- National Natural Science Foundation of China [21202046, 20932002]
- National Basic Research Program of China (973 Program) [2011CB808600]
- Guangdong Natural Science Foundation [S2012040007088]
- China Postdoctoral Science Foundation [2012T50673, 2011M501318]
- Fundamental Research Funds for the Central Universities [2012ZP0003, 2012ZB0011]
An efficient copper-catalyzed method for the synthesis of 2-haloimidazopyridines with aminopyridines and haloalkynes using molecular oxygen as oxidant in a one-pot manner has been developed. In this process, the reaction appears to be very general and suitable for the construction of a variety of 2-halo-substituted imidazopyridines, imidazopyrazines and imidazopyrimidines. The intermolecular oxidative diamination of haloalkynes was achieved for the first time. Importantly, the mild reaction conditions and the efficient conversion of the alkyl-substituted haloalkynes are great improvements over the existing methods. Moreover, the resultant 2-haloimidazo[1,2-a]pyridines could be efficiently converted to other functionalized imidazopyridine products via substitution, coupling reactions and other transformations, which further indicates potential applications of this method in synthetic and pharmaceutical chemistry.
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