Simple, Efficient, and Applicable Route for Synthesis of 2-Aryl(Heteroaryl)-Benzimidazoles at Room Temperature Using Copper Nanoparticles on Activated Carbon as a Reusable Heterogeneous Catalyst

Abstract

A series of 2-(hetero)arylbenzimidazoles were synthesized by the catalytic condensation of (hetero)aryl aldehydes with 1,2-phenylenediamine derivatives at room temperature in the presence of air as the oxidant. Copper nanoparticles on charcoal was employed as an efficient and mild catalyst for this methodology.

Design and synthesis of 2‐phenyl benzimidazole derivatives as VEGFR‐2 inhibitors with anti‐breast cancer activity

“…Benzimidazole nucleus is considered to be a distinctive synthon for building up versatile biologically active molecules. In the last decade, many efforts were devoted for synthesis of various benzimidazole derivatives (Chen et al, 2013;Sharghi, Khalifeh, Mansouri, Aberi, & Eskandari, 2011). The most commonly used synthetic approach typically involves the condensation of o-arylenediamines with carbonyl compounds, like aldehydes, carboxylic acids, or their derivatives, which often requires strong acidic conditions, using elevated temperature or microwave irradiation (Du & Luo, 2010;Lin & Yang, 2005;Salehi, Dabiri, Zolfigol, Otokesh, & Baghbanzadeh, 2006;Tempest et al, 2001).…”

Synthesis of novel benzimidazoles and benzothiazoles via furan‐2‐carboxaldehydes, o‐phenylenediamines, and 2‐aminothiophenol using Cu(II) Schiff‐base@SiO2 as a nanocatalyst

“…One of the most common methods for synthesizing benzimidazole and benzothiazole derivatives is through oxidative cyclization reaction between o ‐phenylenediamines and 2‐aminothiophenol with benzaldehyde. In recent years, the syntheses of benzimidazoles and benzothiazoles were reported using a plethora of catalysts, such as metal–organic framework (MOF) MIL‐101(Cr), [ 24 ] NH 2 ‐MIL‐125(Ti), [ 25 ] MgCl 2 , [ 26 ] Ce(NO 3 ) 3 .6H 2 O, [ 27 ] copper metallovesicles (CuMVs), [ 28 ] Ni‐MCM‐41, [ 29 ] Yb(OTf) 3 , [ 30 ] H 2 O 2 /Fe(NO 3 ) 3 , [ 31 ] vanadium–salen nanoparticles supported on silica, [ 32 ] cobalt–salen complex supported on activated carbon, [ 33 ] copper nanoparticles on charcoal, [ 34 ] Co 2+ complex of [7‐hydroxy‐4‐methyl‐8‐coumarinyl]glycine ([Co(MCG)(H 2 O) 3 ]), [ 35 ] iron‐doped multi‐walled carbon nanotubes (Fe/MWCNTs), [ 36 ] chromium (III)–salen complex nanoparticles on AlPO 4 , [ 37 ] CoFe 2 O 4 @SiO 2 @PAF‐IL, [ 38 ] and 2,6‐dimethyl‐1‐nitropyridin‐1‐ium trinitromethanide [2,6‐DMPy‐NO 2 ]C(NO 2 ) 3. [ 39 ]…”

Highly Active and Reusable Cu/C Catalyst for Synthesis of 5-Substituted 1H-Tetrazoles Starting from Aromatic Aldehydes

“…Previously, we have reported on copper nanoparticles on charcoal (Cu/C) as an excellent heterogeneous cat-alyst for the synthesis of triazole, 38 propargylamine, 39 benzimidazole, 40 2-amino-3-cyanopyridine, 41 indazole 42 and imidazole derivatives. 43 In continuation of our studies on the synthesis of heterocycles and the use of heterogeneous catalysts in organic reactions, [44][45][46][47][48][49][50][51][52][53][54][55][56] we describe here a new strategy for the preparation of tetrazole derivatives.…”