1-Naphthyl-2-cyanoacetamide in heterocyclic synthesis: synthesis and evaluation of the antimicrobial activity of some new pyridine, pyrimidine, and naphtho[2,1-b]oxazine derivatives

摘要

1-Naphthyl-2-cyanoacetamide 1 reacts with arylidene malononitrile to afford a novel 2-oxo-1,2-dihydropyridine-3,5-dicarbonitrile derivative 6. Heating of 1 under reflux with the 1,3-diketones acetylacetone and benzoylacetone furnished the corresponding 3-cyano-2-pyridones derivatives 7 and 8, respectively. Fusion of 1 with 2 mol malononitrile afforded pyridinylacetamide 9. Condensation of 1 with nitrosonaphthols or salicylaldehyde afforded naphthoxazines 11 and 13, or chromene 17, respectively. Coupling of 1 with 4,6-dimethyl-1H-pyrazolo[3,4-b]pyridin-3-diazonium chloride gave the hydrazone 15, which cyclized with acetic acid to afford the corresponding pentaaza derivative 16. Treatment of 1 with DMF-DMA gave acrylamide 19, which when reacted with hydrazine hydrate, o-phenylenediamine, thiourea, or guanidine hydrochloride to afford the corresponding 3-aminopyrazole, diazepine, and pyrimidine derivatives 20, 21, 22, and 23 respectively. The newly synthesized compounds were characterized by elemental analysis and use of spectral data (IR, H-1 NMR, C-13 NMR, and MS).The newly synthesized compounds were tested for their in-vitro antibacterial activity against Gram-positive (Staphylococcus aureus and Bacillus subtilis) and Gram-negative (Pseudomonas aeruginosa and Escherichia coli) bacteria. The results clearly showed that most of the synthesized compounds had mild to moderate activity against the bacteria.