POLY(1,8-NAPHTHYRIDINES) AND 1,9,10-ANTHYRIDINES - MODEL SYSTEMS FOR BLACK ORLON

Condensation reactions of 4-aminopyrimidine-5-carboxaldehyde with aromatic diketones result in the formation of a large number of new bis(o-aminoaldehydes) via hydrolysis of the intermediate pyrido[2, 3-d]pyrimidines. This facile functionalization of a pyridine moiety permits the construction of multiple 1, 8-naphthyridine rings, the building unit of “black Orion”. Attempted polymerizations of these tetrafunctional monomers gave low molecular weight poly(1, 8-naphthyridines) as a result of the very poor solubility of these systems in base-compatible solvents. Condensations in poly(phosphoric acid) were not successful. Phenylated poly(1, 8-naphthyridines) exhibit similar solubility properties. The high reactivity of the 1, 9, 10-anthyridine system and its implication for the structure of “black Orion” are also discussed. © 1979, American Chemical Society. All rights reserved.