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Direct, Catalytic, and Regioselective Synthesis of 2-Alkyl-, Aryl-, and Alkenyl-Substituted N-Heterocycles from N-Oxides

Author:
Larionov, Oleg V., Stephens, David, Mfuh, Adelphe, Chavez, Gabriel
Source:
Organic letters 2014 v.16 no.3 pp. 864-867
ISSN:
1523-7052
Subject:
antimalarials, catalytic activity, chemical reactions, chemical structure, copper, fluorides, heterocyclic nitrogen compounds, lithium, magnesium chloride, regioselectivity
Abstract:
A one-step transformation of heterocyclic N-oxides to 2-alkyl-, aryl-, and alkenyl-substituted N-heterocycles is described. The success of this broad-scope methodology hinges on the combination of copper catalysis and activation by lithium fluoride or magnesium chloride. The utility of this method for the late-stage modification of complex N-heterocycles is exemplified by facile syntheses of new structural analogues of several antimalarial, antimicrobial, and fungicidal agents.
Agid:
5788188