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Abstract The work reported in this thesis is aiming to study the reactivity of 2-oxo(thioxo)pyridine derivatives towards some organic reagents. 3-cyano-4,6-dimethyl-2(1H)-pyridone (1) and pyridin thione (2) have been synthesized. Pyridone (1) reacted with phosphorus oxychloride to give 2-chloropyridine (3), which is reacted with sodium ethoxide, p-anisidine or sodium azide to give the corresponding 2-ethoxy, 2-p-methoxyphenyl amino derivatives (4 and 5), or tetrazolopyridine’ (6), respectively. The 2-oxo(thioxo)pyridines (1,2) underwent base catalyzed condensation with aromatic aldehydes to give 4-styrylpyridene derivative (7) and/or bis-pyridin-4-yl propane derivative (8). Also, 3-cyano-2-oxo(thioxo )pyridines (1,2) were reacted with Grignard reagents to give the corresponding 3-acyl derivatives (9). The 3-acetylpyridone (9a) reacted with phenylhydrazine, hydrazine hydrate, aromatic aldehydes or POCh to give the phenylhydrazone (10), the azine (11), the propenones (12) or 2-chloro-3-acetylpyridine (13), respectively. One the other hand, alkylation of2-oxopyridine (1) by some organic halogen compounds under phase transfer catalysis conditions, afforded predominantly N-alkylation products (14), in addition to 0-alkylation product (15) only in case of methylation, while 2-thioxopyridine (2) yielded, exclusively, the S-alkylated pyridones (17) and thiopheno pyridine (18). However, PIC-alkylation of(1), in presence of CS2, yielded the thin-derivative (16). 2-0xopyridine (1) and its N-methyl derivative (14a) were subjected to react with some reactive dienophiles under thermal Diels-Alder condition to give the corresponding bicycloadducts (20 and 21). Ou the other hand, the 3-cinnamoylpyridone (12b) acting as an a,j3-unsaturated ketone, which is reacted with some active methylene compounds in presence of different catalytic bases at different reaction conditions via a Michael route addition or cycloaddition reaction to give the adducts (22-31). Also, the propenone (12b) is condensed with hydrazines and hydroxylamine to give the corresponding pyridylpyrazolines (32) and isooxazolopyridine (33), respectively. Elemental analysis, IR, 1H-NMR, 13C-NMR and mass spectra were used to establish the structures of the products. |