Merging C–H Bond Functionalization with Amide Alcoholysis: En Route to 2‑Aminopyridines

A new route for the
synthesis of 2-aminopyridines has been developed
that merges C–H functionalization with amide alcoholysis. The
key component of this method is the ability of a quinazolinone to
template the chemo- and regioselective construction of a latent pyridine
ring via site-selective olefinic C–H bond functionalization
under Ru­(II) catalysis. Thus, highly substituted 2-aminopyridines
were prepared in good yield. Mechanistic studies provide insight into
the mechanism of the key oxidative C–H activation/annulation
process.