118468-98-7Relevant articles and documents
Palladium(II) complexes with benzimidazolin-2-ylidene and phosphane ligands and their catalytic activity in Mizoroki-Heck coupling reactions
Tuerkmen, Hayati,Pape, Tania,Hahn, F. Ekkehardt,Cetinkaya, Bekir
, p. 285 - 294 (2009)
Symmetrically and unsymmetrically substituted benzimidazolium bromides (1a-d = NHC·HBr) were synthesized, incorporating bulky benzyl and/or methoxyethyl substituents (a: R = pentamethylbenzyl, R′ = 2-methoxyethyl; b: R = 2,3,5,6-tetramethylbenzyl, R′ = methoxyethyl; c: R, R′ = pentamethylbenzyl; d: R, R′ = 2,3,5,6-tetramethylbenzyl). The salts were used to prepare NHC palladium complexes. Reaction of 1a-d with Pd(OAc) 2 and NaBr in a 1:1:3 ratio in dmso gave mono or dinuclear, bromide-bridged complexes of type 2. Complexes of type 2 react with monodentate or bidentate phosphanes in CH2Cl2 to afford the mixed benzimidazolin-2-ylidene-phosphane complexes 3-6. Reaction of salts 1a-d with Pd(OAc)2 in a 1:2 ratio, in the absence of NaBr, gave complexes trans-[PdBr2(NHC)2] (7). All compounds were fully characterized by NMR spectroscopy, mass spectrometry (MALDI), and elemental analysis. In addition, the molecular structures of 2c, 3c, 3d, and 5b were determined by X-ray diffraction. The catalytic activities of 2-7 in Mizoroki-Heck C-C coupling reactions of aryl halides with n-butyl acrylate are described and compared. Wiley-VCH Verlag GmbH & Co. KGaA, 2009.
Efficient in situ N-heterocyclic carbene palladium(ii) generated from Pd(OAc)2 catalysts for carbonylative Suzuki coupling reactions of arylboronic acids with 2-bromopyridine under inert conditions leading to unsymmetrical arylpyridine ketones: synthesis, characterization and cytotoxic activities
Touj, Nedra,Al-Ayed, Abdullah S.,Sauthier, Mathieu,Mansour, Lamjed,Harrath, Abdel Halim,Al-Tamimi, Jamil,?zdemir, Ismail,Ya?ar, Sedat,Hamdi, Naceur
, p. 40000 - 40015 (2018)
N,N-Substituted benzimidazole salts were successfully synthesized and characterized by 1H-NMR, 13C {1H} NMR and IR techniques, which support the proposed structures. Catalysts generated in situ were efficiently used for the carbonylative cross-coupling reaction of 2 bromopyridine with various boronic acids. The reaction was carried out in THF at 110 °C in the presence of K2CO3 under inert conditions and yields unsymmetrical arylpyridine ketones. All N,N-substituted benzimidazole salts 2a-i and 4a-i studied in this work were screened for their cytotoxic activities against human cancer cell lines such us MDA-MB-231, MCF-7 and T47D. The N,N-substituted benzimidazoles 2e and 2f exhibited the most cytotoxic effect with promising cytotoxic activity with IC50 values of 4.45 μg mL?1 against MDA-MB-231 and 4.85 μg mL?1 against MCF7 respectively.
Ether and coumarin–functionalized (benz)imidazolium salts and their silver(I)–N–heterocyclic carbene complexes: Synthesis, characterization, crystal structures and antimicrobial studies
Achar, Gautam,Agarwal, Purvika,Brinda,Ma?ecki, Jan Grzegorz,Keri, Rangappa S.,Budagumpi, Srinivasa
, p. 64 - 75 (2018)
To explore the impact of different coumarin substituted N–heterocyclic carbene (NHC) ligand backbones on the biological applications of corresponding silver(I) complexes, a series of structurally related ether–functionalized imidazolium (3–5) and benzimidazolium (6–8) hexafluorophosphate salts bearing 6–methylcoumarin, 6–chlorocoumarin and 5,6–benzannulated coumarin substituents, have been reported. These salts have been employed to react with silver(I) oxide at mild reaction conditions to obtain corresponding ionic, bis–NHC coordinated silver(I) hexafluorophosphate complexes (9–14) in excellent yields following in situ deprotonation method. Further, the bromide counterparts of the salts have been treated with silver(I) oxide in dichloromethane to afford neutral mono–NHC coordinated bromido silver(I) complexes (15–20). Both, azolium salts and their silver(I)–NHC complexes, have been thoroughly characterized by 1H and 13C NMR, ATR–IR and elemental analyses. The structure of a benzannulated coumarin substituted imidazolium hexafluorophosphate salt 5 and a silver complex 12 of benzimidazole–based NHC bearing methylcoumarin substituent have been studied through single crystal X–ray diffraction technique. In the case of complex 12, the metal center lies at the inversion center adopting linear coordination geometry with anti– arrangement of the NHC ligands. Feeble π–π stacking interactions between adjacent coumarin rings have been evident in the extended complex structure along with the hydrogen bonding interactions. In the preliminary antibacterial evaluations, silver complexes displayed promising activity with the MIC values in the range 8–64 μg/mL against Staphylococcus aureus, Bacillus subtilis, Escherichia coli and Salmonella typhi, while azolium salts displayed almost no activity.
Synthesis, characterization and tyrosinase inhibitory properties of benzimidazole derivatives
Karatas, Mert Olgun,Alici, Bulent,Cetinkaya, Engin,Bilen, Cigdem,Gencer, Nahit,Arslan, Oktay
, p. 461 - 466 (2014/08/18)
1-Alkylbenzimidazole and 1,3-dialkyl benzimidazolium salts were synthesized and characterized by the data of IR, 1H NMR, 13C NMR spectra and elemental analyses. These compounds were investigated as tyrosinase inhibitors. Tyrosinase h
N-heterocyclic carbene (NHC) palladium(II) complexes bearing chiral oxazoline ligands and their catalytic activities in allylic alkylation reactions
Denizalti, Serpil,Türkmen, Hayati,etinkaya, Bekir
, p. 679 - 685 (2014/12/10)
NHC-Pd(II) complexes bearing a chiral oxazoline ligand (IIIa-f) were synthesized by cleavage of dimeric palladium complexes with the oxazoline ligand. They were fully characterized by 1H and 13C NMR and elemental analyses. The catalytic activity of the complexes (IIIa-f) in allylic alkylation reactions was evaluated. The complex IIIa was found to be the most active catalyst. Very low ee values indicate that the oxazoline is dissociated from the active catalytic species.
RUTHENIUM-BASED COMPLEX CATALYSTS
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Page/Page column 41; 42, (2013/03/26)
The present invention provides novel Ruthenium-based transition metal complex catalysts comprising specific ligands, their preparation and their use in hydrogenation processes. Such complex catalysts are inexpensive, thermally robust, and olefin selective.
Transfer hydrogenation of ketones by ruthenium complexes bearing benzimidazol-2-ylidene ligands
Guerbue, Nevin,Yasar, Sedat,Ozean, Emine Ozge,Ozdemir, Ismail,Cetinkaya, Bekir
scheme or table, p. 3051 - 3056 (2011/01/07)
A series of benzimidazolium ligand precursors were metalated with [RuCl2(p-cymene)]2 to give ruthenium(II) N-heterocyclic carbene complexes. All compounds were fully characterized by elemental analyses, 1H NMR, 13/su
One-pot desulfonylative alkylation of N-sulfonyl azacycles using alkoxides generated by phase-transfer catalysis
Denton, Justin R.
experimental part, p. 775 - 782 (2010/09/11)
Sulfonamide heterocycles, specifically 3-acylindoles, undergo a deprotection/alkylation sequence in the presence of an appropriate alcohol when cesium carbonate or potassium carbonate and a phase-transfer catalyst are utilized. The outcome of the one-pot protocol was found to be significantly dependent on both the alcohol and sulfonamide heterocycle employed. Strictly anhydrous conditions are not necessary for this protocol. Georg Thieme Verlag Stuttgart · New York.
Nitrogen-containing organic compound, resist composition and patterning process
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, (2008/06/13)
Resist compositions comprising nitrogen-containing organic compounds having a benzimidazole structure and a specific ether chain moiety have an excellent resolution, form precisely configured patterns with minimized roughness of sidewalls and are useful in microfabrication using electron beams or deep-UV light.
Synthesis of some benzimidazole derivatives and their antibacterial and antifungal activities
Kuecuekbay, Hasan,Durmaz, Riza,Gueven, Mine,Guenal, Selami
, p. 420 - 424 (2007/10/03)
A number of new benzimidazole derivatives were synthesized by the reaction of benzimidazole with appropriate alkyl halides. The compounds synthesized were intentified by 1H-NMR, Fourier Transformation Infrared (FT-IR) and micro analysis. All new and related compounds studied in this work were screened for their in vitro antimicrobial activities against the standard strains: Enterococcus faecalis (ATCC 29212), Staphylococcus aureus (ATCC 29213), Escherichia coli (ATCC 25922), Pseudomonas aeruginosa (ATCC 27853) and the yeasts Candida albicans and Candida tropicalis. Eleven of the compounds were found effective to inhibit the growth of Gram-positive bacteria (E. faecalis and S. aureus) at MIC values between 12.5-400 μg/ml. None of the compounds exhibited antimicrobial activity against Gram-negative bacteria (E. coli and P. aeruginosa) at the concentrations studied (6.25-800 μg/ml). All compounds (except compound 3) were significantly effective against C. tropicalis with MIC values of 6.25-400 μg/ml. Eight of the tested compounds showed an antifungal activity against C. albicans with a range of the MICs between 50 and 400 μg/ml.
