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

Oleg V. Larionov *, David Stephens , Adelphe Mfuh , and Gabriel Chavez

*Department of Chemistry, University of Texas at San Antonio, One UTSA Circle, San Antonio, Texas 78249, United States, Email: oleg.larionovutsa.edu

O. V. Larionov, D. Stephens, A. Mfuh, G. Chavez, Org. Lett., 2014, 16, 864-867.

DOI: 10.1021/ol403631k (free Supporting Information)


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Abstract

The success of a one-step transformation of heterocyclic N-oxides to 2-alkyl-, aryl-, and alkenyl-substituted N-heterocycles hinges on the combination of copper catalysis and activation by lithium fluoride or magnesium chloride. The utility for the scaffold decoration of a broad range of complex N-heterocycles is exemplified by syntheses of new structural analogues of several antimalarial, antimicrobial, and fungicidal agents.

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Key Words

Quinolines, Pyridines


ID: J54-Y2014