Amides stabilization through conjugation

Pyridone derivatives themselves can be used for aza-annulation. The pyridone tautomers 446 and 447 underwent facile aza-annulation with 47 at ambient temperature (eq. 95).109 In the presence of NaOH, in which the anion was stabilized through conjugation with ester (446) or amide (447) functionality, reaction occurred immediately at ambient temperature to give 448 and 449. 

Tropicamide has p Ta appropriate for a pyridine ring. The second nitrogen is part of an amide group, and is thus a very weak base. Amides are stabilized through resonance, a stabilization that is not possible in the conjugate acid. 

---