Synthesis and characterization of 1-phenyl-3-alkylbenzimidazol-2-ylidene salts and their catalytic activities in the Heck and Suzuki cross-coupling reactions

Journal of Enzyme Inhibition and Medicinal Chemistry

Akkoç²,

Erdoğan

et al. 2016

A series of new benzimidazolium salts (1a-g) were synthesized from the reaction of 1-(4-vinylbenzyl)benzimidazole with various alkyl halides. These salts were used to synthesize silver N-heterocyclic carbene (Ag-NHC) complexes (2a-f). The thirteen compounds were characterized by FT-IR, NMR ( 1 H and 13 C) spectroscopic methods and an elemental analysis technique. These selected candidates were tested for their in vitro antimicrobial activities. Antibacterial and antifungal results indicated that the new salts, and particularly their silver complexes, were found to be strongly effective against seven Gram (À) bacterial strains, three Gram (+) bacterial strains and one yeast (Candida albicans).

Section: Synthesis Of N-heterocyclic Carbene Precursors and Their Silsupporting

confidence: 78%

“…General preparation of 1-(4-vinylbenzyl)-3-alkylbenzimidazolium salts, (1) The synthesis of benzimidazolium salts were prepared according to literature 1,21 . 1-(4-Vinylbenzyl)benzimidazole was synthesized from 4-vinylbenzyl chloride and benzimidazole in ethyl alcohol.…”

Section: Synthesis Of New Compoundsmentioning

confidence: 99%

In vitro antimicrobial studies of new benzimidazolium salts and silver N-heterocyclic carbene complexes

Journal of Enzyme Inhibition and Medicinal Chemistry

Akkoç²,

Erdoğan

et al. 2016

“…The obtained Nalkylbenzimidazole was purified by crystallization. Subsequently, alkyl halide was added to the DMF solution of synthesised N-alkylbenzimidazole and it was stirred for 24 h at 80 C. Benzimidazolium salts were synthesised and purified by crystallisation in a mixture of ethyl alcohol-diethylether (2:1) 17,[22][23][24] . The Ag(I)-NHC complexes (2-6) were synthesised from N-propylphthalimide and N-methyldioxane substituted benzimidazolium salts (1) (2 mmol) and Ag 2 O (1 mmol) in 20 mL dry dichloromethane (Scheme 1).…”

Section: Synthesis and Characterisation Of Ag-nhc Complexes (2-6)mentioning

confidence: 99%

Benzimidazolium-based novel silver N-heterocyclic carbene complexes: synthesis, characterisation and in vitro antimicrobial activity

Sarı

Akkoç

Journal of Enzyme Inhibition and Medicinal Chemistry

et al. 2016

This study reports the synthesis, characterisation and antimicrobial activity of five novel silver N-heterocyclic carbene (Ag-NHC) complexes obtained by N-propylphthalimide and N-methyldioxane substituted benzimidazolium salts with silver oxide. The reactions were performed at room temperature for 24 h in the absence of light. The obtained complexes were identified and characterised by 1 H and 13 C NMR, FT-IR and elemental analysis techniques. The minimum inhibitory concentration (MIC) of the complexes was determined for E. coli, P. aeruginosa, E. faecalis, S. aureus, C. tropicalis and C. albicans in vitro through agar and broth dilution. The results indicated that these complexes exhibit antimicrobial activity. In particular, complex 3 presented the significant broad spectrum antimicrobial activity.

“…Various 1,3‐dialkylbenzimidazolium salts were synthesized by the quaternization of N ‐alkylbenzimidazole with alkyl halides in DMF according to the method reported in the literature . Silver NHC complexes 1a , 1b , 1c , 1d , 1e , 1f , 1g , 1h were obtained by the reaction of benzimidazolium salts with silver oxide in CH 2 Cl 2 at room temperature for 24 h .…”

Section: Resultsmentioning

confidence: 99%

“…Various 1,3-dialkylbenzimidazolium salts were synthesized by the quaternization of N-alkylbenzimidazole with alkyl halides in DMF according to the method reported in the literature. [8,32,33] Silver NHC complexes 1a-1h were obtained by the reaction of benzimidazolium salts with silver oxide in CH 2 Cl 2 at room temperature for 24 h. [28][29][30] Eight novel Pd-NHC complexes 2a-2h were synthesized using complexes 1a-1h as the carbene transfer reagent with PdCl 2 (PhCN) 2 in the presence of CH 2 Cl 2 at 25°C for 24 h in 79-89% yields (Scheme 1). The obtained Pd-NHC complexes are stable against air and moisture.…”

Section: Synthesis Of Pd-nhc Complexesmentioning

confidence: 99%

Catalytic activities in direct arylation of novel palladiumN‐heterocyclic carbene complexes

Akkoç

2014

Applied Organom Chemis

Eight novel palladium N‐heterocyclic carbene (Pd‐NHC) complexes were synthesized by the reaction of chloro 1,3‐dialkylbenzimidazolin‐2‐ylidene silver(I) complexes with bis(benzonitrile)palladium(II) chloride in dichloromethane. These eight Pd‐NHC complexes are as follows: bis[1‐phenyl‐3‐(2,4,6‐trimethylbenzyl)benzimidazol‐2‐ylidene]dichloropalladium(II), bis[1‐phenyl‐3‐(2,3,5,6‐tetramethylbenzyl)benzimidazol‐2‐ylidene]dichloropalladium(II), bis[1‐phenyl‐3‐(2,3,4,5,6‐pentamethylbenzyl)benzimidazol‐2‐ylidene]dichloropalladium(II), bis[1‐phenyl‐3‐(3,4,5‐trimethoxybenzyl)benzimidazol‐2‐ylidene]dichloropalladium(II), bis[1‐(2‐diethylaminoethyl)‐3‐(3‐methylbenzyl)benzimidazol‐2‐ylidene]dichloropalladium(II), bis[1‐(2‐diethylaminoethyl)‐3‐(2,3,5,6‐tetramethylbenzyl)benzimidazol‐2‐ylidene]dichloropalladium(II), bis[1‐(2‐morpholinoethyl)‐3‐naphthalenomethylbenzimidazol‐2‐ylidene]dichloropalladium(II) and bis[1‐(2‐morpholinoethyl)‐3‐(2‐methylbenzyl)benzimidazol‐2‐ylidene]dichloropalladium(II). Also, these synthesized complexes were fully characterized using Fourier transform infrared, 1H NMR and 13C NMR spectroscopic methods and elemental analysis techniques. These synthesized novel Pd‐NHC complexes were tested as catalysts in the direct arylation of 2‐n‐butylthiophene, 2‐n‐butylfuran and 2‐isopropylthiazole with various aryl bromides at 130°C for 1 h. The complexes showed very good catalytic activities in these reactions. Copyright © 2014 John Wiley & Sons, Ltd.