SOME STUDIES OF THE CHEMISTRY OF PYRIDINE-I-OXIDES

The generation of pyridyl-l-oxide carbanions and their subsequent condensation with electrophilic reagents is described. The intermediate carbanions react with bromine and chlorine to give 2,6-dihalopyridine-l-oxides, with sulfur to give biologically active 1-hydroxy-2- pyridinethiones, with oxygen to give 1-hydroxy-2- 4 r pyridones, with benzyl bromide to yield 1-benzyloxy- pyridinium bromide, with epoxides to form polymers, with acetaldehyde and cyclohexanone to give secondary and tertiary alcohols, respectively, and with Schiff bases, to yield secondary amines. A series of bases, other than n-butyllithium, were examined for their ability to generate the pyridyl-l-oxide carbanions. Dehydration and polymerization of some 2-pyridyl alkanol-l-oxides gave poly-(2-vinylpyridine-l-oxide). In vitro pharmacological testing results are given for some of the sulfur compounds prepared