Organic Letters 2013-01-04

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

Robert P Farrell, Maria Victoria Silva Elipe, Michael D Bartberger, Jason S Tedrow, Filisaty Vounatsos

Index: Org. Lett. 15(1) , 168-71, (2013)

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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.