Synthesis of some pyridone derivatives

Chlorination of 6-aryl-3-cyano-2-pyridone-4-carboxylic acid (1) afforded the corresponding acid chloride (2) and the 2-chloro derivative (3). Esterification of (2) gave the corresponding esters (4a; b). Hydrazinolysis of (4a) afforded the respective pyridazinone derivative (5). Treatment of 6-aryl-2-chloro-3-cyano-4-pyridine carboxylic acid (3) with acetyl hydrazine, gave the triazinopyridine derivative (6), while treatment of 3 with sodium azide in DMF afforded the tetrazinopyridine derivative (7). Treatment of the N-acetyl derivative (1b) with thiosemicarbazide and/or hydroxylamine hydrochloride, yielded the correspoding semicarbazone and oxine derivatives (8) and (10), respectively. The reaction of 6-aryl-3-cyano-1,2-dihydro-2-thioxo-4-pyridinecarboxylic acid (1c) with ethylchloro acetate and/or thiourea yielded the mercapto ester derivative (11) and the corresponding pyrido [2,3-d] pyrimidine thione derivative (12). Condensation reaction of (1d) with anthranilic acid, afforded the quinazolone derivative (11). The reactivity of 11 towards hydrazine hydrate was investigated. The structural assignment of the new derivatives were based on IR, 1H NMR and mass data. Some of the new compounds were screened, in vitro, for antimicrobial activity and the results were encouraging.