Synthesis of N<sub>1</sub>‐Substituted Coumarino[4,3‐c]pyrazoles.

Čačić, Milan; Trkovnik, M.; Has‐Schoen, Elizabeta

doi:10.1002/chin.200411130

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“…Unfortunately, most of these methods afford low yields and involve complicated product isolations [20][21][22], although Zhang et al have reported good yields using carbodiimide-based coupling reagents such as 1-hydroxybenzotriazole (HOBt) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) [23]. In connection with our previous work [24][25][26] on the synthesis of coumarins, in the present paper we describe the preparation of the new hydrazide derivatives, heterocycles and Schiff ' s bases from (7-hydroxy-2-oxo-2H-chromen-4-yl )-acetic acid methyl ester.…”

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confidence: 99%

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

Čačić

Trkovnik²,

Čačić

et al. 2006

Molecules

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(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-phenyliminothiazolidin-3-yl) acetamide (15). Molecules 2006, 11 135

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