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

Molecules

Milan Cacic¹  Mladen Trkovnik²  Frane Cacic¹ 

[1] Department of Chemistry, Faculty of Food Technology, J.J. Strossmayer University, Franje Kuhaca 18, 31 000 Osijek, Croatia; ^† E-mail:;Malnara 8, odvojak 7, 10 000 Zagreb, Croatia

关键词: Coumarin hydrazide;    Schiff^’s bases;    thiosemicarbazide;    oxadiazole;    triazole;    thiazolidine;    antimicrobial activity;   

DOI  :  10.3390/11010134

来源: mdpi

【 摘 要 】

(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-2H-chromen-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-oxoethyl] hydrazide (6), 4-phenyl-1-(7-hydroxy-2-oxo-2H-chromen- 4-acetyl) thiosemicarbazide (7), ethyl 3-{2-[2-(7-hydroxy-2-oxo-2H-chromen-4-yl)-acetyl]hydrazono}butanoate (8), (7-hydroxy-2-oxo-2H-chromen-4-yl)-acetic acid N'-[(4-trifluoromethylphenylimino)methyl] hydrazide (9) and (7-hydroxy-2-oxo-2H-chromen-4-yl)acetic acid N'-[(2,3,4-trifluorophenylimino)-methyl] hydrazide (10). Cyclo- condensation 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 carbon disulfide it afforded 7-hydroxy-4-[(5-mercapto-1,3,4-oxadiazol-2-yl)methyl]-2H-chromen-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-phenylimino-thiazolidin-3-yl) acetamide (15).

【 授权许可】

Unknown   
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