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1.
Samaneh Zarei Golzar Komeili Saeed Bahadorikhalili Azadeh Yahya-Meymandi Morteza Karami-Zarandi Bagher Larijani Mahmood Biglar Seyed Esmaeil Sadat Ebrahimi Mohammad Mahdavi 《Journal of heterocyclic chemistry》2020,57(12):4254-4261
In this paper, a novel series of 2-(4-((1-aryl-1H-1,2,3-triazol-4-yl)methoxy)phenyl)2-(2-oxoazetidin-1-yl)acetamide derivatives are synthesized in two steps. The first step involved Ugi multicomponent reaction of β-alanine, o-(propargyl)benzaldehyde and isocyanide derivatives. The product of this step, underwent a click 1,3-dipolar cycloaddition reaction with benzyl azide derivatives. The 2-(4-((1-aryl-1H-1,2,3-triazol-4-yl)methoxy)phenyl)2-(2-oxoazetidin-1-yl)acetamide product was characterized and their antibacterial activities were evaluated against various G-positive (Staphylococcus aureus and Bacillus subtilis) and G-negative (Pseudomonas aeruginosa and Escherichia coli) bacteria, using minimal inhibition concentration. The compounds showed very good antimicrobial activity and a number of products have been more active than ciprofloxacin. 相似文献
2.
N. T. Pokhodylo R. D. Savka V. S. Matiichuk N. D. Obushak 《Russian Journal of General Chemistry》2009,79(2):309-314
By cycloaddition of arylazides to acetylacetone are obtained derivatives of 1,2,3-triazole. In the reaction of 1-[5-methyl-1-(R-phenyl)-1H-1,2,3-triazol-4-yl] ethanones (IIa–IIe) and 1-[4-(4-R-5-methyl-1H-1,2,3-triazol-1-yl)phenyl] ethanones (VIIa-VIIe) with isatin are obtained 2-[1-(R-phenyl)-5-methyl-1H-1,2,3-triazol-4-yl]-4-quinolinecarboxylic acids (IIIa–IIIe) and 2-[4-(4-R-5-methyl-1H-1,2,3-triazol-1-yl)phenyl] -4-quinolinecarboxylic acids (IXa, IXb), respectively. We found that 1-[5-methyl-1-(R-phenyl)-1H-1,2,3-triazol-4-yl] ethanones (IIa–IIe) readily transform into [5-methyl-1-(R-phenyl)-1H-1,2,3-triazol-4-yl] acetic acids (IVa–IVc) by the method of Wilgerodt-Kindler. The (5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)acetic acid reacts with 5-phenyl-4-amino-4H-1,2,4-triazol-3-thiol affording 6-[(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl) methyl]-3-phenyl[1,2,4] triazolo[3,4-b] [1,3,4] thiadiazole (VI).
Original Russian Text ? N.T. Pokhodylo, R.D. Savka, V.S. Matiichuk, N.D. Obushak, 2009, published in Zhurnal Obshchei Khimii,
2009, vol. 79, no. 2, pp. 320–325. 相似文献
3.
Anish Kumar K. S. Madan Kumar 《Phosphorus, sulfur, and silicon and the related elements》2018,193(5):294-299
A new green protocol was developed for the S-alkylation of 2-mercapto-1,3,4-oxadiazole by the reaction of 5-substituted-2-mercapto-1,3,4-oxadiazole with propargyl bromide in sodium bicarbonate in water. The newly synthesized 5-[(substitutedphenoxy)methyl]-2-[(prop-2-yn-1-yl)sulfanyl]-1,3,4-oxadiazole when reacted with azidomethyl coumarins underwent regioselective reaction yielding 4-(((4-((5-((substitutedphenoxy)methyl)-1,3,4-oxadiazol-2-yl)sulfanylmethyl)-1H-1,2,3-triazol-1-yl)methyl)-6-methyl)-2H-chromene-2-one or 1-((4-((5-((substitutedphenoxy)methyl)-1,3,4-oxadiazol-2-yl)sulfanylmethy)-1H-1,2,3-triazol-1-yl-)methyl)-3H-benzo[f]chromene-3-one. Structures of the newly synthesized compounds were confirmed by spectral and analytical data. The compounds were screened for their in-vitro antioxidant property. 相似文献
4.
Research on Chemical Intermediates - A series of novel 3-phenyl-1-(4-(4-((4-(1,4,5-triphenyl-1H-imidazol-2-yl)phenoxy)methyl)-1H-1,2,3-triazol-1-yl)phenyl)prop-2-en-1-one derivatives 6a–j... 相似文献
5.
Rajitha Deshineni Ravibabu Velpula Suneetha Koppu Jyothi Pilli Gyanakumari Chellamella 《Journal of heterocyclic chemistry》2020,57(3):1361-1367
A novel series of ethyl-2-(3-((2-(4-(4-aryl)thiazol-2-yl)hydrazono)methyl)-4-hydroxy/isobutoxyphenyl)-4-methylthiazole-5-carboxylate derivatives ( 4a-f and 5a-f ) were synthesized by employing one-pot multi-component approach involving ethyl 2-(3-formyl-4-oxy/isobutoxyphenyl)-4-methylthiazole-5-carboxylate, thiosemicarbazide and various phenacyl bromides/3-(2-bromoacetyl)-2H-chromen-2-one/2-(2-bromoacetyl)-3H-benzo[f]chromen-3-onein ethanol in the presence of catalytic amount of acetic acid. The structures of all the synthesized compounds were confirmed with spectral analysis, ie, IR, 1H NMR, 13C NMR and mass spectrometry, and all the compounds were screened for their in vitro antimicrobial activity. 相似文献
6.
Nazariy T. Pokhodylo Roman D. Savka Olga Ya. Shyyka Mykola D. Obushak 《Journal of heterocyclic chemistry》2020,57(7):2969-2976
The one-pot CuAAC synthesis of (1H-1,2,3-triazol-1-yl)methyl-1,3,4-oxadiazole and (1H-1,2,3-triazol-1-yl)methyl-1,2,4-oxadiazole derivatives via three-component reaction of consequent nucleophilic substitution of chlorine, with azide, and its further “click” reaction, with alkynes, in the presence of CuI was studied. The utility of newly synthesized 2-(azidomethyl)-1,3,4/1,2,4-oxadiazoles and chloromethyl-1,3,4/1,2,4-oxadiazole derivatives was explored, and their limitations were determined. Novel 5-([4-aryl-1H-1,2,3-triazol-1-yl]methyl)-3-(aryl)-1,2,4-oxadiazoles, 2-([4-aryl-1H-1,2,3-triazol-1-yl]methyl)-5-(aryl)-1,3,4-oxadiazoles were obtained in good yields. 相似文献
7.
Ishani I. Sahay 《合成通讯》2017,47(8):825-834
One pot click chemistry is used to link triazole and benzimidazole pharmacophore to get N-((1-((1H-benzo[d]imidazol-2-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl)aniline and its derivatives. Flexible linkages in the form of –CH2–R or –O–R/–N–R were designed during synthesis. All the newly synthesized compounds were characterized by FT-IR and NMR spectroscopy as well as high-resolution mass spectrometry. Selected compounds were screened for in vitro anti-proliferative activity using National Cancer Institute (NCI)-60 human tumor cell line screening program. The most potent structure N-((1-((1H-benzo[d]imidazol-2-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl)-4-chloroaniline 7e showed 40% growth inhibition in renal cancer cell line (UO-31) at 10?µM concentration. 相似文献
8.
N. T. Pokhodylo O. Ya. Shiika V. S. Matiichuk N. D. Obushak 《Russian Journal of Organic Chemistry》2010,46(3):417-421
2-, 3-, and 4-[5-(1-Aryl-5-R-1H-1,2,3-triazol-4-yl)-1,3,4-oxadiazol-2-yl]pyridines were synthesized from the corresponding 1-aryl-5-R-1H-1,2,3-triazole-4-carbonyl chlorides and 2-, 3-, and 4-(1H-tetrazol-5-yl)-pyridines. 相似文献
9.
B. A. Shainyan V. I. Meshcheryakov I. V. Sterkhova 《Russian Journal of Organic Chemistry》2016,52(7):1032-1035
Three-component heterocyclizations of trifluoro-N-(prop-2-yn-1-yl)methanesulfonamide, trifluoro-N-pheny-N-(prop-2-yn-1-yl)methanesulfonamide, and trifluoro-N,N-di(prop-2-yn-1-yl)methanesulfonamide with formaldehyde and sodium azide afforded N-{[2-(hydroxymethyl)-2H-1,2,3-triazol-4-yl]methyl}-, N-{[2-(hydroxymethyl)-2H-1,2,3-triazol-4-yl]methyl}-N-phenyl-, and N,N-bis{[2-(hydroxymethyl)-2H-1,2,3-triazol-4-yl]methyl}trifluoromethanesulfonamides as the major products together with minor 1-(hydroxymethyl)-1H-1,2,3-triazole isomers. 相似文献
10.
P. Venkateshwarlu M. V. S. R. K. Chaitanya P. K. Dubey 《Phosphorus, sulfur, and silicon and the related elements》2013,188(6):711-721
Abstract of 1,4-dihydro-4-oxo-1,8-naphthyridine-3-carbohydrazide (4) with substituted phenyl isothiocyanates (5) in ethanol under reflux for 30 min gave thiosemicarbazide derivatives 6, which on cyclization in 2N NaOH under refluxing conditions for 1 h resulted in 3-(5-mercapto- 4-phenyl-4H-1,2,4-triazol-3-yl)-1,8-naphthyridin-4(1H)-one (7). Alternatively, 7 could also be prepared from following sequence of reactions, i.e., 4 → 8 → 7. In another sequence of reactions, condensation of 7 with chloroacetic acid in dimethylformamide (DMF) and K2CO3 as a mild base at 120 °C for 2 h resulted in 2-((5-(1,4-dihydro-4-oxo-1,8-naphthyridin-3-yl)-4-phenyl-4H-1,2,4-triazol-3-yl)sulfanyl)acetic acid (10). The latter, on reaction with substituted o-phenylenediamine (11) in 6N HCl for 4 h yielded 3-(5-((1H-benzo[d]imidazol-2-yl)methylthio)-4-phenyl-4H-1,2,4-triazol-3-yl)-1,8-naphthyridin-4(1H)-one (12). Alternatively, 12 could also be prepared by reacting 7 with 13 in DMF and K2CO3 as a mild base at 120 °C for 2 h, followed by oxidation with H2O2 resulting in the corresponding sulfonyl derivatives 14. 相似文献
11.
Boris I. Usachev Sergey A. UsachevGerd-Volker Röschenthaler Vyacheslav Ya. Sosnovskikh 《Tetrahedron letters》2011,52(50):6723-6725
4-Aryl-6-(trifluoromethyl)-2H-pyran-2-ones and ethyl 4-aryl-6-(trifluoromethyl)-2-oxo-2H-pyran-3-carboxylates react with sodium azide to produce highly functionalized CF3-1,2,3-triazoles: 3-[5-(trifluoromethyl)-1,2,3-triazol-4-yl]cinnamic acids and monoethyl esters of [5-(trifluoromethyl)-1,2,3-triazol-4-yl]arylmethylidene malonic acids. 相似文献
12.
Shinde Vikas Mahulikar Pramod Mhaske Pravin C. Nawale Laxman Sarkar Dhiman 《Research on Chemical Intermediates》2018,44(2):1247-1260
Research on Chemical Intermediates - A series of 2-aryl-4-((4-aryl-1H-1,2,3-triazol-1-yl)methyl)thiazole derivatives (8a–p) have been synthesized. The structure of the newly synthesized... 相似文献
13.
Some new 4-(2,6-diarylpyridin-4-yl)-2H-chromen-2-one derivatives 5a–l have been synthesized by reacting 4-(3-oxo-3-arylprop-1-enyl)-2H-chromen-2-ones 3a–c with appropriate 1-(2-oxo-2-arylethyl)pyridinium bromide salt 4a–d in the presence of ammonium acetate in refluxing glacial acetic acid. The newly synthesized compounds have been characterized by elemental and spectral analysis. 相似文献
14.
Stereoselective diazotization of (S)-2-amino-2-phenyl acetic acid (L-phenyl glycine) (4) with NaNO2 in 6% H2SO4 in a mixture of acetone and water gave optically pure (S)-2-hydroxy-2-phenyl acetic acid (L-mandelic acid) (5). Esterification, gave (S)-2-hydroxy-2-phenyl acetic acid esters (6). The latter was treated with chloroacetyl chloride in the presence of triethylamine (TEA) in dichloromethane (DCM) to yield (S)-2-chloroacetyloxy phenyl acetic acid ester (2). In another sequence, the reaction of 2-(chloromethyl)-3-arylquinazolin-4(3H)-one (9) treated with N-Boc piperazine, followed by deprotection of the Boc group, to obtain 3-aryl-2-((piperazin-1-yl)methyl) quinazolin-4(3H)-one (3). Reaction of 2 with 3 in the presence of K2CO3 and KI gave the title compound, 2-(2-(4-((3,4-dihydro-4-oxo-3-arylquinazolin-2-yl)methyl)piperazin-1-yl) acetoyloxy)-2-phenyl acetic acid esters (1). The structures of all the new compounds obtained in the present work are supported by spectral and analytical data. 相似文献
15.
An efficient synthesis of 3-(3-methyl-1-aryl-1H-pyrazol-5-yl)-2H-2-chromen-2-one derivatives by the reaction of salicylaldehydes, 4-hydroxy-6-methyl-2H-pyran-2-one, and arylhydrazine in acetonitrile under reflux condition and in the presence of piperidine is reported. This three-component reaction has some advantages such as ease of handling, good yields, and easy purification. All structures were confirmed by infrared, mass, 1H NMR, and 13C NMR spectroscopy. 相似文献
16.
Vladimir Mironov Gulnara Ivkova Liliya Abdrakhmanova Liliya Burnaeva Kristina Kuzmina 《Phosphorus, sulfur, and silicon and the related elements》2013,188(1-3):162-163
Abstract 2-(5-Methyl-2-phenyl-2Н-1,2,3-diazaphosphol-4-yl)-4H-benzo[d]-1,3,2-dioxaphosphorin-4-one 1 readily reacts with hexafluoroacetone, mesoxalic acid diethyl ester, trifluoropyruvic acid ethyl ester and chloral to give 2-(5-methyl-2-phenyl-2H-1,2,3-dizaphosphole-4-yl)-derivatives of 1,3,2- and 1,4,2-dioxaphosphepines. 相似文献
17.
N. D. Obushak N. T. Pokhodylo N. I. Pidlypnyi V. S. Matiichuk 《Russian Journal of Organic Chemistry》2008,44(10):1522-1527
5-Substituted 2-(1-aryl-5-methyl-1H-1,2,3-triazol-4-yl)-1,3,4-oxadiazoles were synthesized by reaction of 1-aryl-5-methyl-1H-1,2,3-triazole-4-carbonyl chlorides with the corresponding 5-substituted 1H-tetrazoles. 5-Methyl-1-phenyl-1H-1,2,3-triazole-4-carbonyl chloride reacted with N′-hydroxybenzimidamides to give 3-aryl-5-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)-1,2,4-oxadiazoles. Reactions of 4-(5-methyl-1H-1,2,3-triazol-1-yl)benzoic acid with N′-hydroxybenzimidamides resulted in the formation of 3-aryl-5-[4-(5-methyl-1H-1,2,3-triazol-1-yl)phenyl]-1,2,4-oxadiazoles. 相似文献
18.
AbstractA simple, efficient, and metal-free methodology for the preparation of 2-mercaptobenzothiazole and derivatives in excellent yields via microwave-assisted pathway is reported. Our condition provides a convenient protocol for the synthesis of a diverse collection of 2-mercaptobenzothiazoles and 6-(4-substituted-1H-1,2,3-triazol-1-yl)-2-mercaptobenzothiazoles with a very simple purification process. This report provides an alternative protocol for fast access to the wide range of compounds for sequence synthesis and biological studies. 相似文献
19.
Nikolay A. Bumagin Alexey V. Kletskov Sergey K. Petkevich Iryna A. Kolesnik Alexander S. Lyakhov Ludmila S. Ivashkevich Alexander V. Baranovsky Peter V. Kurman Vladimir I. Potkin 《Tetrahedron》2018,74(27):3578-3588
New substituted 3-((1H-1,2,3-triazol-1-yl)methyl)-5-arylisoxazoles (aryl?=?Ph, p-Tol) and 2-(5-phenylisoxazol-3-yl)-5-(2-(1-((5-(p-tolyl)isoxazol-3-yl)methyl)-1H-1,2,3-triazol-4-yl)ethyl)-1,3,4-oxadiazole were synthesized by means of click-chemistry procedures. The obtained compounds were used as ligands in preparation of palladium(II) complexes, and the latter proved to be high-turnover-number catalysts for CC cross-coupling reactions under Green Chemistry conditions. One of the ligands was structurally characterized by single crystal X-ray diffraction, and the structure of complexes was determined by 1H, 13C, 15N NMR spectroscopy and quantum-chemical modeling. 相似文献
20.
1H and13C NMR spectra of 7-diethylamino-4-(1,2,3-triazol-1-yl)-2H-1-benzopyran-2-one derivatives have been studied. The location of the substituent in the 1,2,3-triazole ring was determined by the 2D COLOC method. It was established that the H(3) and H(5) protons in the coumarin moiety experience anisotropic influence of the phenyl subsituent at the C(5) atom in the triazole ring.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1330–1332, July, 1994. 相似文献