This study examined the oxidative polycondensation reaction of 2-[(pyridin-4-yl-) methyleneamino] pyridine-3-ol (2-PMAP) using air $O_2$ and NaOCl oxidants at various temperatures and times in aqueous alkaline and acidic media. Under these reactions, the optimum reaction conditions using air $O_2$ and NaOCl oxidants were determined for 2-PMAP. The number-average molecular weight ($M_n$), weight average molecular weight ($M_w$), and polydispersity index (PDI) values of O-2-PMAP synthesized in aqueous alkaline media were found to be 960, 1230, and $1.281;g;mol^{-1}$ using NaOCl, and 1030, 1520, and $1.476;g;mol^{-1}$ using air $O_2$, respectively. At the optimum reaction conditions, the yield of O-2-PMAP in aqueous alkaline media was 92.50% and 85.70% for air $O_2$ and NaOCl oxidants, respectively. The yield of O-2-PMAP in aqueous acidic media was 88.5% and 88.0% for NaOCl and air $O_2$ oxidants, respectively. O-2-PMAP was characterized by $^1H-$, $^{13}C$-NMR, FT-IR, UV-vis, SEC, and elemental analysis. TGA-DTA analysis revealed O-2-PMAP and its oligomer metal complex compounds, such as $Co^{+2}$, $Ni^{+2}$, and $Cu^{+2}$, to be stable against thermal decomposition and their weight losses at $1000^{circ}C$ were found to be 73.0, 58.0, 53.5%, and 50.0%, respectively. In addition, the antimicrobial activities of the monomer and oligomer were tested against E. Coli (ATCC 25922), E. Faecelis (ATCC 29212), P. Auroginasa (ATCC 27853), and S. Aureus (ATCC 25923).