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An efficient, regioselective amination of 3,5-disubstituted pyridine N-oxides using saccharin as an ammonium surrogate.

Organic letters (2012-12-14)
Robert P Farrell, Maria Victoria Silva Elipe, Michael D Bartberger, Jason S Tedrow, Filisaty Vounatsos
ABSTRACT

A process for the regioselective amination of unsymmetrical 3,5-substituted pyridine N-oxides has been developed utilizing cheap, readily available saccharin as an ammonium surrogate. High conversions of the corresponding saccharin adducts have been achieved under mild reaction conditions. In situ deprotection under acidic conditions allows for a one-pot process to substituted aminopyridines. High regioselectivities were obtained from a variety of 3,5-disubstituted pyridine N-oxides.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Saccharin, ≥98%
Supelco
Mettler-Toledo Calibration substance ME 51143091, Saccharin, traceable to primary standards (LGC)
Sigma-Aldrich
Pyridine N-oxide, 95%
Sigma-Aldrich
Saccharin, ≥99%