24786-40-1Relevant articles and documents
Synthesis of a new class of triazole-linked benzoheterocycles via 1,3-dipolar cycloaddition
Barbosa, Fernanda C. G.,De Oliveira, Ronaldo N.
, p. 592 - 597 (2011)
A new series of 1,2,3-triazole derivatives have been synthesized from phthalimides and terminal alkynes in the presence of a catalytic amount of CuI. The present protocol affords 1,2,3-triazoles in moderate to good yields (44-89percent).
One-Pot Three-Component Synthesis of New Mono- and Bis-1,2,3-triazole Derivatives of 2-Benzimidazolethiol with a Promising Inhibitory Activity against Acidic Corrosion of Steel
Cruz-Gonzalez, Deysi Y.,Gonzalez-Olvera, Rodrigo,Negron-Silva, Guillermo E.,Lomas-Romero, Leticia,Gutierrez-Carrillo, Atilano,Palomar-Pardave, Manuel E.,Romero-Romo, Mario A.,Santillan, Rosa,Uruchurtu, Jorge
, p. 1217 - 1233 (2014)
A series of new mono- and bis-1,2,3-triazole derivatives of 2-benzimidazolethiol were synthesized by three-component copper(I)-catalyzed 1,3-dipolar cycloaddition. The desired heterocycles were obtained in good yields and fully characterized. The corrosion inhibition efficiency of new heterocyclic compounds was investigated on steel grade API 5L X52 in 1 M HCl using electrochemical impedance spectroscopy. The results revealed that these new organic compounds show promising inhibition properties for the corrosion of steel in acidic media. Georg Thieme Verlag Stuttgart New York.
Cyclization of Thiopropargyl Benzimidazoles by Combining Iron(III) Chloride and Diorganyl Diselenides
Goulart, Tales A.C.,Kazmirski, Jo?o A.G.,Back, Davi F.,Zeni, Gilson
, p. 14113 - 14126 (2019)
A practical synthetic approach to the synthesis of 3-(organoselenyl)-imidazothiazines was developed. The methodology involved the regioselective 6-endo-dig cyclization of thiopropargyl benzimidazoles promoted by diorganyl diselenides and iron(III) chloride. The investigation to determine the best reaction conditions indicated the use of thiopropargyl benzimidazoles (0.25 mmol) with diorganyl diselenides (1.0 equiv) and iron(III) chloride (2.0 equiv) in dichloromethane at 40 °C for 30 min to be optimal. Under these conditions, the scope of the substrates was evaluated varying the structures of thiopropargyl benzimidazoles and diorganyl diselenides giving 28 3-(organoselenyl)-imidazothiazines in moderate to good yields. The reaction conditions were also applicable to diorganyl ditellurides; however, they did not work for diorganyl disulfides. The mechanism studies were carried out indicating that the cyclization proceeds via a cooperative action of diorganyl diselenides and iron(III) chloride, but a direct electrophilic cyclization, promoted by the in situ formed electrophilic organoselenium species, cannot be ruled out.
A Palladium Iodide-Catalyzed Cyclocarbonylation Approach to Thiadiazafluorenones
Veltri, Lucia,Paladino, Veronica,Plastina, Pierluigi,Gabriele, Bartolo
, p. 6106 - 6111 (2016)
The first example of an additive cyclocarbonylation process leading to 1-thia-4a,9-diazafluoren-4-ones is reported. This process is based on the reaction of readily available 2-(propynylthio)benzimidazoles with carbon monoxide carried out in EtOH at 100 °C under a 5/2 mixture of CO-CO2 at 70 atm in the presence of the PdI2/KI catalytic system. Experimental evidence suggests a mechanistic pathway involving N-palladation of the substrate followed by CO insertion, triple bond insertion, protonolysis, and isomerization.
Design, Synthesis, Spectroscopic Characterisation and In Vitro Cytostatic Evaluation of Novel Bis(coumarin-1,2,3-triazolyl)benzenes and Hybrid Coumarin-1,2,3-triazolyl-aryl Derivatives
Pr?ir, Kristina,Horak, Ema,Kralj, Marijeta,Uzelac, Lidija,Liekens, Sandra,Steinberg, Ivana Murkovi?,Kri?tafor, Svjetlana
, (2022/01/24)
In this work, a series of novel 1,2,3-triazolyl-coumarin hybrid systems were designed as potential antitumour agents. The structural modification of the coumarin ring was carried out by Cu(I)-catalysed Huisgen 1,3-dipolar cycloaddition of 7-azido-4-methylcoumarin and terminal aromatic alkynes to obtain 1,4-disubstituted 1,2,3-triazolyl-coumarin conjugates 2a–g, bis(1,2,3triazolyl-coumarin)benzenes 2h–i and coumarin-1,2,3-triazolyl-benzazole hybrids 4a–b. The newly synthesised hybrid molecules were investigated for in vitro antitumour activity against five human cancer cell lines, colon carcinoma HCT116, breast carcinoma MCF-7, lung carcinoma H 460, human T-lymphocyte cells CEM, cervix carcinoma cells HeLa, as well as human dermal microvascular endothelial cells (HMEC-1). Most of these compounds showed moderate to pronounced cytotoxic activity, especially towards MCF-7 cell lines with IC50 = 0.3–32 μM. In addition, compounds 2a–i and 4a–b were studied by UV-Vis absorption and fluorescence spectroscopy and their basic photophysical parameters were determined.
Synthesis of novel benzimidazole and benzothiazole derivatives bearing a 1,2,3-triazole ring system and their acetylcholinesterase inhibitory activity
Faraji, Laleh,Shahkarami, Shiva,Nadri, Hamid,Moradi, Alireza,Saeedi, Mina,Foroumadi, Alireza,Ramazani, Ali,Haririan, Ismaeil,Ganjali, Mohammad Reza,Shafiee, Abbas,Khoobi, Mehdi
, p. 30 - 35 (2017/02/15)
A series of 20 novel benzimidazole and benzothiazole derivatives linked to a 1,2,3-triazole ring system was synthesised, characterised and evaluated for in vitro acetylcholinesterase (AChE) inhibitory activity. Several copper catalysts and solvents were screened to establish the optimal conditions for the preparation of the target compounds. Three different linkers were used to optimise the enzyme inhibitory effect. Out of the 20 compounds, 13 showed some AChE inhibition. The most potent compound, which showed 84% inhibition at 100 μM, contained a 1-(2-fluorobenzyl)-1,2,3-triazole linked to a benzimidazole group. A docking simulation study showed that the most active compound bound preferentially to the catalytic anionic subsite of the AChE enzyme.
The activity of magnesium/aluminum 'memory effect' reconstructed hydrotalcites in the microwave-assisted synthesis of 2-benzimidazolethiol and its alkylated derivatives
Cruz-Gonzalez, Deysi Y.,González-Olvera, Rodrigo,Angeles-Beltrán, Deyanira,Negrón-Silva, Guillermo E.,Santillan, Rosa
, p. 3281 - 3287 (2013/12/04)
An efficient and practical methodology for the microwave-assisted synthesis of 2-benzimidazolethiol from 1,2-benzenediamine and carbon disulfide using reconstructed hydrotalcite is described. The corresponding mono- and dialkylated derivatives of 2-benzimidazolethiol were obtained generally in good to excellent yields after short reaction times. Reconstructed hydrotalcite proved to be an efficient and reusable heterogeneous base for the alkylation reactions. Georg Thieme Verlag Stuttgart New York.
Ultrasound-assisted synthesis of 1-N-β-D-glucopyranosyl-1H-1,2,3- triazole benzoheterocycles and their anti-inflammatory activities
Da Silva, Gilson B.,Guimara?es, Bruna M.,Assis, Shalom P. O.,Lima, Vera L. M.,De Oliveira, Ronaldo N.
, p. 914 - 921 (2013/08/23)
In this work,the preparation of various glucosyl triazoles from a reaction between 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl azide and terminal alkynes was developed in moderate to excellent yields (63-99percent). Ultrasound energy was applied at each step of the reaction to increase chemical reactivity. In addition,the compounds conjugated with benzoheterocycles moieties revealed potent anti-inflammatory activity.
Interaction of benzimidazole-2-thione with propargyl bromide and 1,3-dibromopropyne
Yaroshenko,Nakhmanovich,Larina,Elokhina,Amosova
experimental part, p. 1129 - 1134 (2009/05/26)
Interaction of benzimidazole-2-thione with propargyl bromide under found conditions permitted the direct synthesis of 2-(2-propynylsulfanyl)-3H-1,3- benzimidazolium bromide, the base 2-(2-propynylsulfanyl)-1H-1,3-benzimidazole, stable crystalline 2-(1,2-propadienylsulfanyl)-1H-1,3-benzimidazole, and 3-methyl[1,3]thiazolo[3,2-a][1,3]benzimidazole. The reaction of benzimidazole-2-thione with 1,3-dibromopropyne in chloroform or absolute methanol gave 2-(3-bromo-2-propynylsulfanyl)-3H-1,3-benzimidazolium bromide, and in absolute methanole in the presence of a twofold excess of sodium methoxide the reaction proceeded stereo-and regioselectively to give 3-[(Z)- bromomethylidene][1,3]thiazolo[3,2-a][1,3]benzimidazole.
A new method of synthesis of triazolobenzimidazole
Zniber, Rachid,Moussaif, Ahmed,Achour, Redouane,Ghoul, Mostafa E.L.,Hakam, Asmae,Souhassou, Mohamed
, p. 157 - 161 (2007/10/03)
Condensation between dipole 1,3 and 2-alkylthiobenzimidazole was studied. We obtained some compounds derived from triazolobenzimidazole. All the molecules were characterized by 1H NMR, IR, mass and X-rays.
