Merck
CN
  • Direct, catalytic, and regioselective synthesis of 2-alkyl-, aryl-, and alkenyl-substituted N-heterocycles from N-oxides.

Direct, catalytic, and regioselective synthesis of 2-alkyl-, aryl-, and alkenyl-substituted N-heterocycles from N-oxides.

Organic letters (2014-01-15)
Oleg V Larionov, David Stephens, Adelphe Mfuh, Gabriel Chavez
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Phenanthridine, 98%
Sigma-Aldrich
2-Phenylpyridine, 98%
Sigma-Aldrich
Isoquinoline N-oxide, 98%
Sigma-Aldrich
Pyrazine, ≥99%
Sigma-Aldrich
5,7-Dichloro-8-quinolinol, 99%
Sigma-Aldrich
o-Tolylmagnesium chloride solution, 1.0 M in THF
Sigma-Aldrich
Phenethylmagnesium chloride solution, 1.0 M in THF
Sigma-Aldrich
3-Chloroperbenzoic acid, ≤77%
Sigma-Aldrich
Benzylmagnesium chloride solution, 2.0 M in THF
Sigma-Aldrich
Quinoline N-oxide hydrate, 97%
Sigma-Aldrich
Isoquinoline, 97%
Supelco
Quinoxyfen, PESTANAL®, analytical standard
Sigma-Aldrich
Quinoxaline, ≥98%
Sigma-Aldrich
5-Chloro-8-quinolinol, 95%
Sigma-Aldrich
Isopropylmagnesium chloride solution, 2.0 M in THF
Sigma-Aldrich
Phenylmagnesium chloride solution, 2.0 M in THF
Sigma-Aldrich
4,7-Dichloroquinoline, 97%
Sigma-Aldrich
Quinoline, reagent grade, 98%
Sigma-Aldrich
8-Hydroxyquinoline, ACS reagent, 98.5%