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  • A simple Cu-catalyzed coupling approach to substituted 3-pyridinol and 5-pyrimidinol antioxidants.

A simple Cu-catalyzed coupling approach to substituted 3-pyridinol and 5-pyrimidinol antioxidants.

The Journal of organic chemistry (2008-11-04)
Susheel J Nara, Mukund Jha, Johan Brinkhorst, Tony J Zemanek, Derek A Pratt
ABSTRACT

A convenient approach to 3-pyridinols and 5-pyrimidinols via a two-step Cu-catalyzed benzyloxylation/catalytic hydrogenation sequence is presented. The corresponding 3-pyridinamines and 5-pyrimidinamines can be prepared in an analogous sequence utilizing benzylamine in lieu of benzyl alcohol. The radical-scavenging ability of these derivatives are preliminarily explored and reveal that the increased acidities of the pyridinols and pyrimidinols render them susceptible to more significant kinetic solvent effects when compared to phenols.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Propionitrile, 99%
Sigma-Aldrich
Propionitrile, purum, ≥99.0% (GC)
Supelco
Propionitrile, analytical standard
Sigma-Aldrich
5-Bromo-2-nitropyridine, 99%