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Synthesis and Antimicrobial Activity of Some Derivatives on the Basis (7-hydroxy-2-oxo-2H-chromen-4-yl)-acetic Acid Hydrazide

(7-Hydroxy-2-oxo-2H-chromen-4-yl)-acetic acid hydrazide (2) was prepared from (7-hydroxy-2-oxo-2H-chromen-4-yl)-acetic acid ethyl ester (1) and 100% hydrazine hydrate. Compound 2, is the key intermediate for the synthesis of several series of new compounds such as Schiff's bases 3a-l, formic acid N'-[2-(7-hydroxy-2-oxo-2Hchromen- 4-yl)- acetyl]-hydrazide (4), acetic acid N'-[2-(7-hydroxy-2-oxo-2H-chromen-4-yl)-acetyl]-hydrazide (5), (7-hydroxy-2-oxo-2H-chromen-4-yl)-acetic acid N'-[2-(4-hydroxy-2-oxo-2H-chromen-3-yl)-2-oxo-ethyl]-hydrazide (6), 4-phenyl-1-(7-hydroxy-2- oxo-2H-chromen-4-acetyl)-thiosemicarbazide (7), ethyl 3-{;2-[2-(7-hydroxy-2-oxo-2Hchromen- 4-yl)-acetyl]hydrazono};butanoate (8), (7-hydroxy-2-oxo-2H-chromen-4-yl)- acetic acid N'-[(4-trifluoromethyl-phenylimino)-methyl]-hydrazide (9) and (7-hydroxy-2-oxo-2H-chromen-4-yl)-acetic acid N'-[(2, 3, 4-trifluorophenylimino)-methyl]-hydrazide (10). Cyclocondensation of compound 2 with pentane-2, 4-dione gave 4-[2-(3, 5-dimethyl- 1H-pyrazol-1-yl)-2-oxoethyl]-7-hydroxy-2H-chromen-2-one (11), while with carbondisulfide it afforded 7-hydroxy-4-[(5-mercapto-1, 3, 4-oxadiazol-2-yl)methyl]-2Hchromen- 2-one (12) and with potassium isothiocyanate it gave 7-hydroxy-4-[(5- mercapto-4H-1, 2, 4-triazol-3-yl)methyl]-2H-chromen-2-one (14). Compound 7 was cyclized to afford 2-(7-hydroxy-2-oxo-2H-chromen-4-yl)-N´-(4-oxo-2-phenyliminothiazolidin-3-yl)-acetamide (15).

coumarin hydrazide; Schiff's bases; thiosemicarbazide; oxadiazole; triazole

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