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1.
Synthesis and antimicrobial activity of some derivatives of (7-hydroxy-2-oxo-2H-chromen-4-yl)-acetic acid hydrazide 总被引:1,自引:0,他引:1
(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). 相似文献
2.
Venkatesh Talavara Upendranath K. Nayaka Y. Arthoba 《Journal of Solid State Electrochemistry》2021,25(4):1237-1244
Journal of Solid State Electrochemistry - A new 7-{[1H-indol-3-ylmethylidene]amino}-4-methyl-2H-chromen-2-one dye (3) was synthesized by the reaction of 7-amino-4-methyl coumarin with... 相似文献
3.
To study the intramolecular Diels-Alder cycloadditon of 2H-chromen-2-one as a diene, a series of chiral N-allyl-N-benzylamides that contain a 2H-chromen-2-one moiety were designed for the synthesis of benzo[f]isoindol-1-ones via an intramolecular Diels-Alder and a subsequent retro-Diels-Alder cycloaddition with the expulsion of CO2. Both the yield (80%-89%) and absolute stereocontrol of the tandem reaction were high when an electron-withdrawing group was attached to the dienophile. The double bond in the styrene substructure remained in the products could be further derivatized by dihydroxylation. 相似文献
4.
It was established that the direction of the reaction of 3-(1,3-dioxobutan-1-yl)-2H-chromen-2-one with bromine depends on
the conditions under which it is carried out. In acidic media carbocyclization occurs with the formation of dihydroxanthylium
bromide or hydroxyxanthene; in chloroform enolization of the carbonyl group with subsequent bromination and heterocyclization
to substituted pyranochromene with the participation of the benzopyran-2-one fragment occurs. 相似文献
5.
Nematollahi D Azizian J Sargordan-Arani M Hesari M Jameh-Bozorghi S Alizadeh A Fotouhi L Mirza B 《Chemical & pharmaceutical bulletin》2008,56(11):1562-1566
The 4-(dihydroxyphenylthio)-2H-chromen-2-one derivatives have been synthesized by direct electrochemical oxidation of catechols in the presence of 4-mercaptocoumarin as a nucleophile in water/acetonitrile (50/50) solution, in a one-pot process, at carbon rod electrode, in an undivided cell and in constant current conditions, through an EC mechanism. The products are characterized by spectra data. Besides, the difference in electrochemical oxidation of catechol in the presence of 4-hydroxycoumarin and 4-mercaptocoumarin explained by computational structure, natural bond orbital (NBO) analysis and density functional theory (DFT: B3LYP/6-31G*//B3LYP/6-31G*) based methods, using the GAUSSIAN 98 package of programs. 相似文献
6.
《Tetrahedron: Asymmetry》2003,14(11):1489-1493
4-Oxo-3,4-dihydro-2-chromen-3-yl acetate is synthesized using manganese(III)acetate starting from 2,3-dihydro-4H-chromen-4-one. K2CO3 mediated hydrolysis of 4-oxo-3,4-dihdro-2-chromen-3-yl acetate furnished 3-hydroxy-2,3-dihydro-4H-chromen-4-one in high yield.The enantioselective hydrolysis of (±)-4-oxo-3,4-dihydro-2-chromen-3-yl acetate in various organic solvent-phosphate buffer (pH7) systems and enantioselective transesterification of (±)-3-hydroxy-2,3-dihydro-4H-chromen-4-one in organic solvents was investigated by screening a range of lipases. The lipase Amano PS, PPL, PLE and CCL-catalyzed asymmetric ester hydrolysis and transesterification afforded the enantiomers of 3-hydroxy-2,3-dihydro-4H-chromen-4-one and 4-oxo-3,4-dihydro-2-chromen-3-yl acetate with high enantiomeric excess (up to 97% ee) and in good yields. 相似文献
7.
New coumarin derivatives, namely 7-[(5-amino-1,3,4-thiadiazol-2-yl)methoxy]-2H-chromen-2-one, 5-[(2-oxo-2H-chromen-7-yloxy)methyl]-1,3,4-thiadiazol-2(3H)-one, 2-[2-(2-oxo-2H-chromen-7-yloxy)acetyl]-N-phenylhydrazinecarbothioamide, 7-[(5-(phenylamino)-1,3,4-thiadiazol-2-yl)methoxy]-2H-chromen-2-one and 7-[(5-mercapto-4-phenyl-4H-1,2,4-triazol-3-yl)methoxy]-2H-chromen-2-one were prepared starting from the natural compound umbelliferone. The newly synthesized compounds were characterized by elemental analysis and spectral studies (IR, 1H-NMR and 13C-NMR). 相似文献
8.
A spectrophotometric method has been developed for the determination of Molybdenum (VI) using 3-hydroxy-2-(2'-thienyl)-4H-chromen-4-one as a complexing agent. The complex formed was dissolved in water in the presence of Triton X-100 and exhibits an absorption maximum at 410 nm. A large number of metal ions like Co(II), Ni(II), Mn(II), Cr(III), Zn(II), Cu(II), Hg(II), Bi(III), Fe(II), Fe(III), Zr(IV), V(V) can be tolerated at an appreciable concentrations. Molar absorptivity and Sandell's sensitivity of the method is 2.80 x 10(5) l mol-1cm-1 and 3.42 x 10(-4) micrograms cm-2, respectively. Beer's law is obeyed in the concentration range of 0.01-0.4 ppm Mo(VI). Aliquots containing 0.2 ppm of Mo(VI) give a mean absorbance of 0.56 with a relative standard deviation of 1.3%. 相似文献
9.
《Arabian Journal of Chemistry》2022,15(9):104088
In this work, 4-(((4-ethyl-5-(thiophen-2-yl)-4H-1,2,4-triazole-3-yl)thio)methyl)-7,8-dimethyl-2H-chromen-2-one was synthesized by acetone-mediated condensation of 4-ethyle-5-(thiophen-2-yl)-4H-1,2,4-triazole-3-thiol and 4-(chloromethyl)-7,8-dimethyl-2H-chromen-2-one. The molecule results (3) were experimentally characterized using FT-IR, 1H-, and 13C NMR spectroscopy. Density Functional Theory (B3LYP/cc-pVDZ) was used to investigate the ideal molecule structure, vibrational frequencies, and 1H with 13C NMR (theoretically) chemical shifts. Theoretical and experimental spectroscopy results were compared and agreed with each other, which indicated the validity of the used developed molecular structure. The Dipole moment, hardness, softnes, electronegativity, electrophilicity index, nucleophilicity index, and chemical potential as electronic structural parameters linked to corrosion inhibition efficacy were investigated for the prepared compound. Furthermore, the fraction of transferred electrons was calculated to determine the interaction between the iron surface and organic molecules. The results indicated a favorable relationship between organic-based corrosion inhibitors and quantum chemical parameters processes. The corrosion inhibitors' behavior can be predicted without the need for experimental investigation. 相似文献
10.
Anoop Kumar Chhakkar Lajpat Rai Kakkar 《Fresenius' Journal of Analytical Chemistry》1995,351(8):720-723
A coloured complex of niobium (V) with 3-hydroxy-2-(2-thienyl)-4H-chromen-4-one (HTC) is produced in perchloric acid medium (4 mol/L); it is quite stable and extractable into dichloromethane. Beer's law is obeyed in the range 0.0–1.9 g Nb(V) mL–1. The molar absorptivity at max=420 nm is 5.0357×104 L mol–1 cm–1. Using Job's method and the mole ratio method, the ratio of metal to ligand (Nb:HTC) in the extracted species has been found to be 1:2. The effect of anions and foreign metals is described. 相似文献
11.
12.
Slepukhin P. A. Fatykhov R. F. Sharapov A. D. Valieva M. I. Starnovskaya E. S. Khalymbadzha I. A. Kopchuk D. S. Zyryanov G. V. Chupakhin O. N. 《Russian Journal of General Chemistry》2022,92(7):1285-1289
Russian Journal of General Chemistry - The molecular and crystal structures of 8-(3,6-diphenylpyridin-2-yl)-5,7-dimethoxy-4-phenyl-2H-chromen-2-one,... 相似文献
13.
Russian Chemical Bulletin - 4-Methyl-7-(4-methyl-2-oxo-2H-chromen-6-yl)disulfanyl-2H-chromen-2-one hydrotriiodide was synthesized by the reaction of 7-mercapto-4-methylcoumarin with iodine, and its... 相似文献
14.
4-Hydroxy-2H-chromen-2-one and 4-hydroxy-2H-chromene-2-thione reacted with allyl bromide, 1,1,3-trichloroprop-1-ene, and 1,3-dichlorobut-2-ene to give the corresponding ethers, which were oxidized to (2-oxo-2H-chromen-4-yloxy)acetic acid with potassium permanganate, and various derivatives of that acid were obtained. 3-(3,3-Dichloroprop-2-enyl)-7-hydroxy-4-methyl-2H-chromen-2-one and 3-(3,3-dichloroprop-2-enyl)-7-hydroxy-4-methyl-2H-chromene-2-thione were synthesized, and some their transformations were studied. 相似文献
15.
E. A. Abu-Gharib R. M. El-Khatib L. A. E. Nassr A. M. Abu-Dief 《Kinetics and Catalysis》2012,53(2):182-187
Kinetics of the base hydrolysis of 6-nitro-2H-chromen-2-one (NC) and 6-nitro-2H-chromen-2-one-3-carboxylic acid (NCC) in water-methanol
and water-acetone mixtures was studied at temperature range from 283 to 313 K. The activation parameters of the reactions
were evaluated and discussed. The change in the activation barrier of the investigated compounds from water to water-methanol
and water-acetone mixtures were estimated from the kinetic data. The base hydrolysis of NC and NCC in the water-methanol and
water-acetone mixtures follows a rate law with k
obs = k
2[OH−] and k
obs = k
1 + k
2[OH−], respectively. The decrease in the rate constants of NC and NCC hydrolysis, as the proportion of methanol and acetone increases,
is accounted for by the destabilization of the OH− ion. The activation and thermodynamic parameters were determined. 相似文献
16.
P. F. Vlad D. P. Popa E. C. Gorincioi M. N. Coltsa G. N. Mironov 《Russian Chemical Bulletin》2000,49(1):98-101
A synthetic route to 11-hydroxydrim-8(9)-en-7-one and 11,12-hydroxydrim-8(9)-en-7-one, valuable key intermediates for the
preparation of naturally occurring biologically active drimanic sesquiterpenoids, starting from easily available drim-8(9)-en-7-one
was developed. 11-Hydroxydrim-8(9)-en-7-one was obtained by peracidic oxidation of the enol acetate of drim-8(9)-en-7-one.
11,12-Dihydroxydrim-8(9)-en-7-one was synthesized from drim-8(9)-en-7-one by two routes, namely, by a five-step procedurevia 11-hydroxydrim-8(9)-en-7-one and by bromination of drim-8(9)-en-7-one with NBS to give 11,12-dibromodrim-8(9)-en-7-one followed
by its acetoxylation and deacetylation.
Deceased
Translated fromIzvestiya Akademii Nauk, Seriya Khimicheskaya, No. 1, pp. 95–98, January, 2000. 相似文献
17.
P. F. Vlad D. P. Popa E. C. Gorincioi M. N. Coltsa G. N. Mironov 《Russian Chemical Bulletin》1990,49(1):98-101
A synthetic route to 11-hydroxydrim-8(9)-en-7-one and 11,12-hydroxydrim-8(9)-en-7-one, valuable key intermediates for the
preparation of naturally occurring biologically active drimanic sesquiterpenoids, starting from easily available drim-8(9)-en-7-one
was developed. 11-Hydroxydrim-8(9)-en-7-one was obtained by peracidic oxidation of the enol acetate of drim-8(9)-en-7-one.
11,12-Dihydroxydrim-8(9)-en-7-one was synthesized from drim-8(9)-en-7-one by two routes, namely, by a five-step procedurevia 11-hydroxydrim-8(9)-en-7-one and by bromination of drim-8(9)-en-7-one with NBS to give 11,12-dibromodrim-8(9)-en-7-one followed
by its acetoxylation and deacetylation.
Deceased
Translated fromIzvestiya Akademii Nauk, Seriya Khimicheskaya, No. 1, pp. 95–98, January, 2000. 相似文献
18.
K. V. Shcherbakov Ya. V. Burgart V. I. Saloutin 《Russian Journal of Organic Chemistry》2006,42(12):1838-1844
5,6,7,8-Tetrafluoro-4-hydroxy-2H-chromen-2-one reacts with methylamine to give methylammonium 5,6,7,8-tetrafluoro-2-oxo-2H-chromen-4-olate, regardless of the solvent. The reaction of 3-acetyl-5,6,7,8-tetrafluoro-4-hydroxy-2H-chromen-2-one with the same amine in ethanol or acetonitrile leads to the formation of methylammonium 3-acetyl-5,6,7,8-tetrafluoro-2-oxo-2H-chromen-4-olate, while in dimethyl sulfoxide 5,6,8-trifluoro-7-methylamino-3-(1-methylaminoethylidene)-3,4-dihydro-2H-chromene-2,4-dione is formed. The latter is also formed in the reaction of 5,6,7,8-tetrafluoro-4-hydroxy-3-(1-iminoethyl)-2H-chromen-2-one with methylamine in DMSO, whereas in ethanol and acetonitrile 5,6,7,8-tetrafluoro-3-(1-methylaminoethylidene)-3,4-dihydro-2H-chromene-2,4-dione is obtained. 5,6,7,8-Tetrafluoro-3-(1-methylaminoethylidene)-3,4-dihydro-2H-chromene-2,4-dione reacts with methylamine, yielding 7-mono-or 5,7-bis(methylamino)-substituted derivatives. 相似文献
19.
20.
Cheng Gang ZHANG Bo Gang LI Xiang Ge ZHOU Guo Lin ZHANG* Chengdu Institute of Biology Chinese Academy of Sciences Chengdu Chengdu Institute of Organic Chemistry Chinese Academy of Sciences Chengdu 《中国化学快报》2004,15(3):269-272
Phenanthroindolizidine and phenanthroquinolizidine are closely related groups of alkaloids. Since the first isolation of tylophorine 1 in 1935, these natural products have attracted much attention because of their interesting biological activities such as antitumor activity1-3. The obvious problems such as toxicity to nerve system, instability and uneconomical synthetical pathways restrict its application. Kozma reported that C-9, C-14 of tylophorine 1 and C-9, C-15 of cryptopleurine 2 we… 相似文献