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Domino Reactions Involving the Branched C–N and CC Cleavage of Enaminones Toward Pyridines Synthesis

Author:
Wan, Jie-Ping, Zhou, Youyi, Cao, Shuo
Source:
Journal of organic chemistry 2014 v.79 no.20 pp. 9872-9877
ISSN:
1520-6904
Subject:
ammonium chloride, carbon, chemical reactions, chemical structure, cleavage (chemistry), organic chemistry, pyridines
Abstract:
The copper-catalyzed cascade reactions of enaminones and ammonium chloride have led to the unprecedented synthesis of 4-unsubstituted pyridines of both symmetrical and unsymmetrical structures. Under the aerobic copper-catalyzed conditions, the branched transformations of enaminones with C–N and CC bond cleavage provide the C2-C3/C5-C6 and C4 building blocks to construct the pyridine ring, respectively. The CC cleavage that provides the C4 atom in the pyridine product is the first example showing the reactivity of an enaminone as the donor of one carbon synthon.
Agid:
5502872