A novel Co2+ ion functional benzoxazine monomer based on phenol and 2-aminopyridine was prepared, polymerized by step-wise curing and characterized via direct pyrolysis mass spectrometry in addition to classical spectrometry techniques. Curing of neat monomer yielded a highly cross-linked polymer as a consequence of competing and consecutive reactions involving the heterocyclic ring opening followed by attack of -NCH2 groups to ortho and para positions of phenol and pyridine rings and coupling of --NCH2 groups. On the other hand, the coordination of metal ion to nitrogen atoms of the pyridyl rings inhibited the attack of -NCH2 groups to ortho and para positions of pyridine rings and eventually decreased the extent of cross-linking. (C) 2014 Elsevier Ltd. All rights reserved.