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1.
Abdelrahman E. F. Shehta W. Assy M. G. M. Farhan M. E. 《Russian Journal of Organic Chemistry》2020,56(10):1832-1839
Russian Journal of Organic Chemistry - Condensation of 5-methyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one with 4-hydroxybenzaldhyde in alcoholic sodium hydroxide yielded... 相似文献
2.
Naguib H. M. Dauoud N. T. Shaban S. N. Abdelghaffar N. F. Sayed G. H. Anwer K. E. 《Russian Journal of Organic Chemistry》2022,58(6):891-904
Russian Journal of Organic Chemistry - 4-(Arylmethylidene)-5-methyl-2,4-dihydro-3H-pyrazol-3-ones were prepared via one-pot reaction of ethyl acetoacetate, hydrazine hydrate, and aromatic aldehydes... 相似文献
3.
Ichizo Okabayashi 《Journal of heterocyclic chemistry》1980,17(6):1339-1339
2,4-Dihydro-5-methyl-2-phenyl-4-(9H-xanthen-9-yl)-3H-pyrazol-3-one ( 3 ) was prepared by the condensation of phenylhydrazine and ethyl α-acetyl-9H-xanthene-9-acetate ( 2 ), or 9H-xanthen-9-ol ( 1 ) and 2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one ( 4 ). 5-Amino-2,4-dihydro-2-phenyl-4-(9H-xanthen-9-yl)-3H-pyrazol-3-one ( 6 ) was obtained by the condensation of 1 and 5-amino-2,4-dihydro-2-phenyl-3H-pyrazol-3-one ( 5 ). 相似文献
4.
Solvent extraction of65zinc,60cobalt and152+154europium from aqueous buffers into benzene containing 4-thiobenzoyl-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one (SBMPP)
has been investigated in detail (μ=0.1, T=26±1°C). The species extracted and the values of log Kex, where Kex refers to the extraction equilibrium, are ZnL2 (−2.68) CoL2(−3.08) and EuL3(−7.08), where L is the anion of the ligand. The sulfur analog appears to be more effective than the parent ligand 4-benzoyl-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one
in the extraction of zinc(II) and cobalt(II), whereas the reverse is true with europium(III). 相似文献
5.
Ichizo Okabayashi 《Journal of heterocyclic chemistry》1982,19(2):437-438
2,4-Dihydro-5-methyl-2-phenyl-4-(9H-thioxanthen-9-yl)-3H-pyrazol-3-one ( 3 ) was prepared by condensing 9H-thioxanthen-9-ol ( 1 ) with 2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one ( 2 ), or by cyclizing ethyl α-acetyl-9H-thioxanthene-9-acetate ( 4 ) with phenylhydrazine. 2,4-Dihydro-5-methyl-2-phenyl-4-(9H-thioxan- then-9-yl)-3H-pyrazol-3-one 10,10-dioxide ( 8 ) was prepared by cyclizing ethyl α-acetyl-9H-thioxanthene-9-acetate 10,10-dioxide ( 7 ) with phenylhydrazine. Compound 8 was also obtained by oxidizing 3 with hydrogen peroxide in acetic acid. 5-Amino-2,4-dihydro-2-phenyl-4(9H-thioxanthen-9-yl)-3H-pyrazol-3-one ( 10 ) was obtained by condensing 1 with 5-amino-2,4-dihydro-2-phenyl-3H-pyrazol-3-one ( 9 ). 相似文献
6.
Novel Cu(II), Co(II), Ni(II), and Zn(II) complexes of 5-methyl-2-phenyl-4-[(4-phenylazo)anilinemethylylidene]- 2,4-dihydro-3H-pyrazole-3-thione and 5-methyl-4-[4-methyl-2-(4-methylphenylazo)anilinemethylylidene]- 2-phenyl-2,4-dihydro-3H-pyrazole-3-thione, i.e. ligands containing the phenylazo group in the ortho and para positions of the aniline fragment, were synthesized by the chemical and electrochemical methods. The complexes and ligands were characterized by IR, 1H NMR, X-ray absorption spectroscopy and magnetochemistry. The azo group of the ligands is not involved in coordination to the metal. 相似文献
7.
Therkelsen FD Hansen AL Pedersen EB Nielsen C 《Organic & biomolecular chemistry》2003,1(16):2908-2918
Condensation of 3-(3,5-dimethylphenyl)-2-oxocyclopentanecarboxamide (11) with oxalyl chloride and condensation of ethyl 2-benzylamino-5-methyl-3-phenylcyclopent-1-enecarboxylate (17a) with trimethylsilyl isothiocyanate gave 7-(3,5-dimethylphenyl)-6,7-dihydro-5H-cyclopenta[e][1,3]oxazine-2,4-dione (12) and 1-benzyl-5-methyl-7-phenyl-2-thioxo-1,2,3,5,6,7- hexahydrocyclopentapyrimidin-4-one (18a), respectively. Acid catalyzed ring-closure of 6-(4-methyl-1-phenylpent-3-enyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one (26) and radical mediated ring-closure of 1,3-bis(benzyloxymethyl)-5-bromo-6-(1-phenylbut-3-enyl)-1H-pyrimidine-2,4- dione (32a) gave 5,5-dimethyl-8-phenyl-5,6,7,8-tetrahydro-1H-quinazoline-2,4- dione (28) and 1,3-bis(benzyloxymethyl)-5-methyl-7-phenyl-1,5,6,7- tetrahydrocyclopentapyrimidine-2,4-dione (33), respectively. Annelated emivirine analogues 7-(3,5-dimethylphenyl)-1- ethoxymethyl-1,5,6,7-tetrahydrocyclopentapyrimidine-2,4-dione (4), 1-ethoxymethyl-5,5-dimethyl-8-phenyl-5,6,7,8-tetrahydro-1H-quinazoline- 2,4-dione (5) and 1-ethoxymethyl-5-methyl-7-phenyl-1,5,6,7- tetrahydrocyclopentapyrimidine-2,4-dione (6) were obtained in few steps from 12, 28 and 18a/33, respectively. These new analogues can be considered as conformationally locaTed analogues of emivirine. However, the compounds 4 6 showed lower activities against HIV-1 than emivirine and it is concluded that the locked conformation disfavours activity against HIV-1. 相似文献
8.
Nadiia V. Pikun Natalya P. Kolesnyk Eduard B. Rusanov Aiva Plotniece Martins Rucins Arkadij Sobolev Yuriy G. Shermolovich 《Tetrahedron》2018,74(23):2884-2890
Electrophilic fluorination of Hantzsch-type 1,4-dihydropyridines with Selectfluor® led to the formation of new fluorinated 2,6-heptanediones - dialkyl 2,4-diacetyl-2,4-difluoro-3-phenylpentanedioates. Novel 2,6-heptanedione derivatives in reaction with hydrazine hydrate easily form 6-amino-4,7-difluoro-3-hydroxy-1,3-dimethyl-5-oxo-8-phenyl-2-oxa-6-azabicyclo[2.2.2]octanes instead of the corresponding diazepine derivatives. The obtained 2-оxa-6-azabicyclo[2,2,2]octanes are thermally stable at the temperatures below 50°С. At higher temperatures rearrangement of 2-oxa-6-azabicyclo[2,2,2]octanes offers new fluorine-containing pyrazolinone derivatives - alkyl esters of 2-fluoro-2-((4-fluoro-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-4-yl)(phenyl)methyl)-3-oxobutanoates. 相似文献
9.
Ethyl 2-{2-[4-(2,3-dimethyl-5-oxo-1-phenyl-3-(pyrazolin-4-yl)]-2-cyano-1-(phenylamino)vinylthio}-acetate, 2-[4-(2,3-dimethyl-5-oxo-1-phenyl-(3-pyrazolin-4-yl))(1,3-thiazol-2-yl)]2-(4-oxo-3-phenyl-(1,3-thiazoilidin-2-ylidene))ethanenitrile, 2-[4-(2,3-dimethyl-5-oxo-1-phenyl(3-pyrazolin-4-yl))(1,3-thiazol-2-yl)]-2-(4-methyl-3-phenyl(1,3-thiazolin-2-ylidene))ethanenitrile, 2-(5-acetyl-4-methyl-3-phenyl(1,3-thiazolin-2-ylidene))-2-[4-(2,3-dimethyl-5-oxo-1-phenyl(3-pyrazolin-4-yl))(1,3-thiazol-2-yl)]ethanenitrile, and ethyl 2-(cyano(4-(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)thiazol-2-yl)methylene)-2,3-dihydro-4-methyl-3-phenylthiazole-5-carboxylate were synthesized by treatment of 2-(4-(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)thiazol-2-yl)-3-mercapto-3-(phenylamino)-acrylonitrile with appropriate halo ketones or halo esters. Also, 4-{2-[5,7-dimethyl-2-(phenylamino)(7a-hydropyrazolo[1,5-a]pyrimidin-3-yl](1,-thiazol-4-yl)}-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one derivatives were synthesized via reaction of 4-{2-[5-amino-3-(phenylamino)pyrazolin-4-yl](1,3-thiazol-2-yl)}-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one with β-diketone or β-keto ester. All synthesized compound were established by elemental analysis, spectral data, and alternative synthesis whenever possible. 相似文献
10.
A. S. Burlov S. A. Mashchenko A. S. Antsyshkina G. G. Sadikov V. S. Sergienko M. A. Kiskin S. A. Nikolaevskii V. G. Vlasenko Ya. V. Zubavichus A. I. Uraev D. A. Garnovskii E. V. Korshunova S. I. Levchenkov 《Russian Journal of Coordination Chemistry》2013,39(12):813-821
New complexes of Cu(II), Co(II), and Ni(II) with 1-phenyl-3-methyl-4-[(4-phenylazophenyl)hydrazono]-5H-pyrazol-5-one and 1-phenyl-3-methyl-4-[4-methyl-2-(4-methylphenylazophenyl)hydrazono]-5H-pyrazol-5-one are synthesized by the chemical and electrochemical methods and characterized by IR, 1H NMR, and EXAFS spectroscopy and X-ray diffraction analysis. Depending on the complexing metal and position of the additional azo group, the latter is involved or not in coordination with the metal to form heterounit five- and six-membered metallocycles. 相似文献
11.
Russian Journal of Organic Chemistry - Condensation of 5-methyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one with p-hydroxybenzaldehyde in alcoholic sodium hydroxide yielded... 相似文献
12.
Holzer W Claramunt RM Pérez-Torralba M Guggi D Brehmer TH 《The Journal of organic chemistry》2003,68(21):7943-7950
Reaction of 1-substituted 4-acyl-5-hydroxy-3-methyl-1H-pyrazoles (2) with hydroxylamine gives the corresponding "oximes" 3, which are mainly present as (Z)-2,4-dihydro-4-[(hydroxyamino)methylene]-3H-pyrazol-3-ones. Treatment of compounds 3 with trichloroacetyl isocyanate/potassium carbonate in anhydrous diethyl ether affords 7-methyl-1,5,6-triazaspiro[2.4]hepta-1,6-dien-4-ones (4). The structure of compounds 4 was elucidated by means of single-crystal X-ray analysis (4f, 4h) and confirmed by NMR spectroscopic investigations ((1)H, (13)C). 相似文献
13.
The extraction equilibria of Co(II) and Zn(II) complexes with 4-benzoyl-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one in
the presence of tributyl phosphate have been investigated in eight ‘inert’ solvents employing the radioisotopes cobalt-60
and zinc-65. The activity coefficients of different species in the organic phase and the solubility parameter of the adduct
have been calculated with the help of regular solution theory. A regularity is observed in the correlation between the adduct
formation constant and the activity coefficient of the species. 相似文献
14.
Schiff base derivatives have gained great importance due to revealing a great number of biological properties. Schiff bases were synthesized by treatment of 4-amino-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one ( 1 ) with various aldehydes in methanol at reflux. In addition, diamine was reacted with an aldehyde to yield the corresponding Schiff bases. The structures of synthesized Schiff bases were elucidated by spectroscopic methods such as microanalysis, 1H-NMR, 13C-NMR, and FTIR. Antioxidant activities of synthesized Schiff bases were carried out using different antioxidant assays such as 1,1-diphenyl-2-picryl-hydrazyl free radical (DPPH•) scavenging, 2,2′-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS) radical scavenging, and reducing power activity. (E)-4-((1H-indol-3-yl)methyleneamino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one ( 3 ), (E)-1,5-dimethyl-4-((2-methyl-1H-indol-3-yl)methyleneamino)-2-phenyl-1H-pyrazol-3(2H)-one ( 5 ), (E)-1,5-dimethyl-2-phenyl-4-(thiophen-2-ylmethyleneamino)-1H-pyrazol-3(2H)-one ( 7 ), (E)-1,5-dimethyl-2-phenyl-4-(quinolin-2-ylmethyleneamino)-1H-pyrazol-3(2H)-one ( 9 ), (1S,2S,N1,N2)-N1,N2-bis((1H-indol-3-yl)methylene)cyclohexane-1,2-diamine ( 11 ), and (1S,2S,N1,N2)-N1,N2-bis((2-methyl-1H-indol-3-yl)methylene)cyclohexane-1,2-diamine ( 12 ) were synthesized in high yields. Compound 5 displayed a good ABTS•+ activity. Compound 3 revealed the outstanding activity in all assays. Compound 7 has the best-reducing power ability in comparison to other synthesized compounds. Although compounds 5, 11, 12 are new, compounds 3, 7, 9 are known. Due to revealing a good antioxidant activity, the synthesized compounds ( 3, 5, 7 ) have the potential to be used as synthetic antioxidant agents. 相似文献
15.
G. P. Okonnishnikova I. V. Kostyuchenko E. V. Shulishov Yu. V. Tomilov 《Russian Chemical Bulletin》2006,55(12):2233-2237
Cyclopropyldiazonium generated by basic decomposition of N-cyclopropyl-N-nitrosourea easily entered into an azo coupling reaction with 5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one (2) to give the corresponding cyclopropylhydrazone in up to 90% yield. Competitive processes occurring under the conditions
of cyclopropyldiazonium generation by nitrosation of cyclopropylamine with butyl nitrite mainly include nitrosation of the
starting pyrazolone 2. Subsequent transformations of the resulting heterocyclic 3-methyl-1-phenyl-1H-pyrazole-4,5-dione 4-oxime yield 4-[cyclopropyl(oxido)imino]-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2151–2155, December, 2006. 相似文献
16.
A series of 1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one-containing Schiff bases were synthesized, characterized and screened for their antibacterial activities. The structures of the synthesized compounds were established by spectroscopic (FT-IR, 1H-NMR, 13C-NMR, MS) and elemental analyses. The anti-bacterial activities (with MIC values) of compounds were evaluated. The anti-bacterial screening results reveal that among the six compounds screened, four compounds showed moderate to good anti-bacterial activity. Among the tested compounds, the most effective compounds against four bacterial strains, viz. Escherichia coli, Staphylococcus aureus, Salmonella typhimurium and Streptococcus pyogenes, are [(2-chlorobenzylidene)amino]-1,5-dimethyl-2-phenyl-1,2-dihydropyrazol-3-one (4) and [(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-ylimino)methyl]benzonitrile (5) with MIC values of 6.25 μg/mL. 相似文献
17.
The molecular structures of two byproducts 1,1'-diphenyl-3',4'-dihydrodispiro[indole-2,2'-furan-5',2'-indole]-3,3'(1H, 1'H)-dione (3) and 1,5'-diphenyl-4',5'-dihydro-3'H-spiro[indole-2,2'-pyrano[3,2-b]indol]-3(1H)-one (4), which accompanied the rearrangement of 3-hydroxy-3-methyl-1-phenylquinoline-2,4(1H,3H)-dione (1) to 2-hydroxy-2-methyl-1-phenyl-1,2-dihydro-3H-indol-3-one (2), have been elucidated by NMR, MS, and X-ray diffraction. 相似文献
18.
Condensation of 3-benzoyl-4-phenyl-2-pyrazoline with various aryl phosphorodichloridates or trichloromethylphosphonic dichloride in the presence of a base resulted in the formation of arylbis (3-benzoyl-4,5-dihydro-4-phenyl-1H-pyrazol-1-yl)phosphinates and trichloromethyl-bis (3-benzoyl-4,5-dihydro-4-phenyl-1H-pyrazol-1-yl)phosphonate. The structures of the title compounds were confirmed by elemental analyses, IR, 1H, 13C, and 31P NMR spectra. The EI mass spectrum of one member of the family is discussed. These compounds were found to possess good antibacterial and antifungal activity. © 1997 John Wiley & Sons, Inc. 相似文献
19.
Gordon W. Gribble Erin T. Pelkey Wendy M. Simon Hernando A. Trujillo 《Tetrahedron》2000,56(52):10133-10140
The unsymmetrical mesoionic münchnones 13 (3-benzyl-2-methyl-4-phenyl-1,3-oxazolium-5-olate) and 14 (3-benzyl-4-methyl-2-phenyl-1,3-oxazolium-5-olate) react with the N-protected 2- and 3-nitroindoles 1 (ethyl 2-nitroindole-1-carboxylate), 6 (3-nitro-1-(phenylsulfonyl)indole), and 17 (ethyl 3-nitroindole-1-carboxylate) in refluxing THF to afford in good to excellent yields the pyrrolo[3,4-b]indoles 15 (2-benzyl-1-methyl-3-phenyl-4-carboethoxy-2,4-dihydropyrrolo[3,4-b]indole), 16 (2-benzyl-3-methyl-1-phenyl-4-carboethoxy-2,4-dihydropyrrolo[3,4-b]indole), 18 (2-benzyl-1-methyl-3-phenyl-4-(phenylsulfonyl)-2,4-dihydropyrrolo[3,4-b]indole), and 19 (2-benzyl-3-methyl-1-phenyl-4-(phenylsulfonyl)-2,4-dihydropyrrolo[3,4-b]indole). In several cases the regiochemistry, which is opposite to that predicted by FMO theory, is very high and leads essentially to a single pyrrolo[3,4-b]indole; e.g., 6+13→19 in 74% yield. 相似文献
20.
Thirupaiah Bade 《合成通讯》2013,43(20):2350-2354
The synthesis of 3-(2-(5-(benzylideneamino)-3-phenyl-1H-pyrazol-1-yl)thiazol-4-yl)-4-hydroxy-6-methyl-2H-pyran-2-one derivatives was achieved through a one-pot, four-component reaction involving condensation of 3-(2-bromoacetyl)-4-hydroxy-6-methyl-2H-pyran-2-one, thiosemicarbazide, phenacylcyanaide, and various aryl aldehydes in dry alcohol and few drops of acetic acid under reflux condition. This four-component reaction has some advantages such as ease of handling, good yields, and easy workup. All structures of newly prepared compounds were confirmed by analytical and spectral data. 相似文献