6123-63-3Relevant academic research and scientific papers
Regio- and stereoselective synthesis of spiro-heterocycles bearing the pyrazole scaffold via [3+2] cycloaddition reaction
Islam, Mohammad Shahidul,Haukka, Matti,Soliman, Saied M.,Al-Majid, Abdullah Mohammed,Rahman, A.F.M. Motiur,Bari, Ahmed,Barakat, Assem
, (2021/10/27)
Herein we reported the utility of one-pot multicomponent based [3+2] cycloaddition reaction transformation to prepare a new two hybrids of spirooxindoles engrafted with pyrazole skeleton. Upon treatment of the electron-deficient olefins based pyrazole motif with in situ the generated azomethine ylides (AY) of sarcosine with the 6-chloro-isatin afforded spiroadducts. To enlighten the regio- and diastereo-selectivity of these spiroheterocycles, single crystal X-ray diffraction analysis was presented. Using Hirshfeld calculations, many short distance contacts such as O…H, Cl…H, N…H, H…C, C…C and Cl…S have a great impact on the molecular packing and the crystal stability of 8a and 8b. The latter showed some Cl…Cl inter halogen interactions (Cl1…Cl3; 3.358 ?). In addition, DFT calculations were used to compute the electronic properties as well as the 1H- and 13C-NMR spectra of the studied systems. Both compounds are polar where 8b (3.995 Debye) has higher dipole moment than 8a (3.414 Debye). The NMR chemical shifts were calculated and found in excellent correlations between the calculated and experimental data were obtained (R2 = 0.94–0.98).
Reactivity and Anticancer Assessment of 4-Hydroxyquinoline Derivatives
El-Metwally, S. A.,Regal, M. K. A.,Shabana, S. S.
, p. 307 - 314 (2020/04/17)
Abstract: Ethyl 4-hydroxy-7-(trifluoromethyl)quinoline-3-carboxylate (1) exhibits a moderate cytotoxic activity against the MCF-7 mammary gland cancer cell line and HePG2 hepatocellular carcinoma cell line and a weak activity against the HCT-116 human colorectal carcinoma cell line. In order to enhance the cytotoxic activity of this compound, it was modified by changing the side-chain substituent and/or forming a new heterocyclic ring fused to the pyridine ring. Heating compound 1 with chloroacetyl chloride gave a mixture of two isomeric O-acylation products ethyl 4-(2-chloroacetoxy)-7-(trifluoromethyl)-quinoline-3-carboxylate and 3-chloro-8-(trifluoromethyl)-2H-pyrano[3,2-c]quinoline-2,4(3H)-dione, whereas the reaction with acetyl chloride in NaOH formed an N-acylation product 1-acetyl-4-oxo-7-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylic acid. The reactions of compound 1 with urea, thiourea, hydrazine hydrate, hydroxylamine, o-phenylenediamine, phenyl isothiocyanate, and ethyl acetoacetate yielded the corresponding condensation products 1-[4-oxo-7-(trifluoromethyl)-3,4-dihydroquinoline-3-carbonyl)]urea, 1-[4-oxo-7-(trifluoromethyl)-3,4-dihydroquinoline-3-carbonyl)]thiourea, 7-(trifluoromethyl)-1,2-dihydropyrazolo[4,3-c]quinolin-3-one, 7-(trifluoromethyl)isoxazolo[4,5-c]quinolin-3(2H)-one, 3-(trifluoromethyl)-13H-benzo[2,3][1,4]diazepino[6,5-c]quinolin-7-ol, 3-phenyl-2-thioxo-8-(trifluoromethyl)-2,3-dihydro-4H-[1,3]oxazino[5,6-c]quinolin-4-one and ethyl 8-(trifluoromethyl)-2-methyl-4-oxo-4H-pyrano[3,2-c]quinolone 3-carboxylate, respectively. The structures of the synthesized compounds were confirmed by elemental analysis and spectral data.
N → N acyl group migration in N-acylpyrazoles: Isomerization of 1,4-diacyl-5-methyl-1H-pyrazoles to 1,4-diacyl-3-methyl-1H-pyrazoles
Petrov,Pakal’nis,Zerov,Yakimovich
, p. 381 - 392 (2017/05/10)
1,4-Diacyl-5-methyl-1H-pyrazoles on heating in toluene undergo isomerization to 1,4-diacyl-3-methyl-1H-pyrazoles via intermolecular N → N acyl group migration. 1,4,5-Trisubstituted pyrazoles obtained by reaction of 2-ethoxymethylidene derivatives of 1,3-diketones with 1,3-benzothiazol-2-ylhydrazine or phenylhydrazine failed to isomerize to 1,3,4-trisubstituted pyrazoles.
2-Bromo-1-(1H-pyrazol-4-yl)ethanone: Versatile Precursor for Novel Mono- and Bis[pyrazolylthiazoles]
Salem, Mostafa E.,Darweesh, Ahmed F.,Mekky, Ahmed E. M.,Farag, Ahmad M.,Elwahy, Ahmed H. M.
, p. 226 - 234 (2017/02/03)
The synthesis of novel bis(thiazoles) 20a, 20b, 20c and 23a, 23b, 23c is reported. Thus, reaction of 2-bromo-1-(5-methyl-1-phenyl-1H-pyrazol-4-yl)ethanone (6) with the corresponding thioamide derivatives 7a,7b, in refluxing EtOH in the presence of triethylamine, afforded 4-pyrazolylthiazoles 8a, 8b in good yields. On the other hand, the novel bis(thiazoles) 20a, 20b, 20c and 23a, 23b, 23c were obtained from the reaction of 6 with the corresponding benzaldehyde thiosemicarbazones 19a, 19b, 19c, 22a, 22b, 22c in refluxing EtOH. Compounds 19a, 19b, 19c and 22a, 22b, 22c were obtained by condensation of the corresponding bis(aldehydes) 18a, 18b, 18c and 21a, 21b, 21c with thiosemicarbazide.
2-Bromo-1-(1H-pyrazol-4-yl)ethanone: Versatile precursors for novel mono-, bis- and poly{6-(1H-pyrazol-4-yl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines}
Salem, Mostafa E.,Darweesh, Ahmed F.,Farag, Ahmad M.,Elwahy, Ahmed H.M.
, p. 712 - 719 (2016/01/15)
A simple synthesis of novel mono-, bis- and poly{6-(1H-pyrazol-4-yl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines} is reported. The formation of the target compounds was achieved by the reaction of 2-bromo-1-(5-methyl-1-phenyl-1H-pyrazol-4-yl)ethanone with the appropriate aminotriazolethiol or by the reaction of 6-pyrazolyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine-3-thiol with the appropriate di- and poly(bromo) compounds. The structures of the newly synthesized compounds were established by spectroscopy and elemental analyses.
Design and regioselective synthesis of trifluoromethylquinolone derivatives as potent antimicrobial agents
Garudachari,Isloor, Arun M.,Satyanarayana,Fun, Hoong-Kun,Pavithra,Kulal, Ananda
, p. 422 - 432 (2013/10/01)
Three series of new trifluoromethyl substituted quinolone derivatives were synthesized (4a-f, 6a-f and 8a-f) from corresponding substituted anilines by multi-step reactions. The regioselective alkylation with different alkyl halides were carried out by approaching two different routes to get the final products in good yield. Newly synthesized compounds were characterized by spectral study and also by C, H, N analyses. Three dimensional structure of 2b and 4b were also confirmed by single crystal X-ray studies. The final compounds (4a-f, 6a-f and 8a-f) were screened for their in-vitro antibacterial and antifungal activity by well plate method (zone of inhibition). The results revealed that, compounds 4a, 6b, 6c and 8e showed significant antibacterial activity as compared to the standard drug Ciprofloxacin. The compound 8a was found to be a potent antifungal agent.
One-pot regioselective synthesis of 1,4,5-trisubstituted pyrazoles under solvent-free conditions without catalyst
Alinezhad, Heshmatollah,Tajbakhsh, Mahmood,Zare, Mahboobeh
experimental part, p. 947 - 950 (2012/08/07)
A fast, one pot method with excellent yield has been developed for preparation of 1,4,5-trisubstituted pyrazoles. Treatment of β-dicarbonyl compounds with N,N-dimethylformamide dimethylacetal and hydrazine derivatives afforded immediately the desired pyrazoles under solvent-free conditions in the absence of catalyst. Springer-Verlag 2012.
Catalyst-free one-pot synthesis of 1,4,5-trisubstituted pyrazoles in 2,2,2-trifluoroethanol
Alinezhad, Heshmatollah,Tajbakhsh, Mahmood,Zare, Mahboobeh
experimental part, p. 995 - 1000 (2011/11/06)
A simple, efficient and three component one-pot synthesis of 1,4,5-trisubstituted pyrazoles by condensation of β-dicarbonyls, N,N-dimethylformamide dimethyl acetal (DMFDMA) and hydrazine derivatives in 2,2,2-trifluoroethanol without using any catalyst and activation, is described.
Synthesis of 1-aryl-5-methyl-4-[4-aryl-6-(3-oxo-1,4-benzothiazin-6-yl) pyrid-2-yl]pyrazoles and 1-aryl-5-methyl-4-[2-amino-4-aryl-pyrimidin-6-yl] pyrazoles as antibacterial agents
Ashok,Pallavi,Jagath Reddy,Srinivasa Rao
, p. 33 - 37 (2008/09/19)
A series of 1-Aryl-5-methyl-4-[4-aryl-6-3-oxo-1,4-benzothiazin-6-yl)pyrid- 2-yl]pyrazoles (6a-g) and 1-Aryl-5-methyl-4-[2-amino-4-arylpyrimidin-6-yl] pyrazoles (7a-d) have been synthesized and tested for their antibacterial activity.
Aqueous one-pot synthesis of pyrazoles, pyrimidines and isoxazoles promoted by microwave irradiation
Molteni, Valentina,Hamilton, Matthew M.,Mao, Long,Crane, Christine M.,Termin, Andreas P.,Wilson, Dean M.
, p. 1669 - 1674 (2007/10/03)
Microwave irradiation promotes the conversion of enaminoketones formed in situ into a variety of heterocycles by reaction with the appropriate bidentate nucleophile. The advantages of the method over previous approaches are short reaction times and facile purification by precipitation of the products in aqueous media. Moreover the convenient one-pot procedure makes these syntheses particularly suitable for library production. Organic reactions in aqueous media have become of great interest as water is not only more environmentally friendly, but also because organic reactions in water often display unique reactivity and selectivity.
