Dm. Andrews et al., POTENTIAL MECHANISM-BASED TYROSINE KINASE INHIBITORS .1. PHOSPHORYLATION CHEMISTRY OF PYRIDINE N-OXIDES, Journal of the Chemical Society. Perkin transactions. I, (8), 1995, pp. 1045-1048
Phosphorylated derivatives of 4-picoline N-oxide have been observed on
treatment with both phosphorylating and phosphitylating agents. These
intermediates were trapped by external nucleophiles. Propane-1-thiol
reacted preferentially at carbon to yield a propylsulfanylpyridine whe
reas propylamine reacted preferentially at phosphorus. This chemistry
carries implications for the design of mechanism-based tyrosine kinase
inhibitors.