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CuCl/air-mediated oxidative coupling reaction of imidazoheterocycles with N-aryl glycine esters

Author:
Jiao, Jing, Zhang, Jun-Rong, Liao, Yan-Yan, Xu, Li, Hu, Maolin, Tang, Ri-Yuan
Source:
RSC advances 2017 v.7 no.48 pp. 30152-30159
ISSN:
2046-2069
Subject:
air, copper, esters, imines, pyridines
Abstract:
A copper/air mediated oxidative coupling reaction of imidazoheterocycles with N-aryl glycine esters is here described. The reaction proceeded effectively under an air atmosphere without the use of peroxide agents. This simple protocol allows for the preparation of a wide range of imidazoheterocycles with a glycine ester motif, which are of great interest in the field of medicinal chemistry. Interestingly, the coupling of imidazo[1,2-a]pyridine with secondary or tertiary α-amino phenylethanone selectively affords the imidazo[1,2-a]pyridin-3-yl imine or imidazo[1,2-a]pyridin-3-yl diketone in the presence of CuCl and TBHP (tertbutyl hydroperoxide).
Agid:
6420119