Solventless synthesis of 2-aryl-1-arylmethyl-1H-1,3-benzimidazoles catalyzed by Fe(ClO4)3 at room temperature

“…The proposed mechanism is based on Heravi's report for the synthesis of 1,2-disubstituted bzim [14]. At first there is the formation of a double Schiff base via condensation (Scheme 2a), this is followed by protonation of the imine nitrogen (wet solvent is the source of protons), then a nucleophilic attack of the non-protonated nitrogen atom to the adjacent sp 2 carbon gives a reaction intermediate (Scheme 2b) that could suffer a hydride 1,3-transposition to generate the bzim ligand (Scheme 2c).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and characterization of new types of aluminum and gallium complexes stabilized by bifunctional ligands

Vengoechea-Gómez

Cortés-Llamas

Muñoz‐Hernández

2014

Main Group Chemistry

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Novel mononuclear metal complexes with the general formula {[(NC 4 H 3 ) 2 CH 2 -CNNC 6 H 2 (R 2 )]MMe 2 } (M=Ga, R=H (1); M=Al, R=Me (2)) and {[(OC 4 H 2 CH 3 ) 2 CH 2 -CNNC 6 H 4 ]MMe 3 } (M=Ga (3); M=Al (4)) results when benzimidazole derivatives ligands are mixed with trimethylaluminum and trimethylgallium. The X-ray crystal structures of 1 and 4 are described.The structural data revealed that 1 is a mononuclear gallium compound with the pendant pyrrol moiety coordinated to the metal center, while 4 is a mononuclear aluminum complex that does not show any kind of interaction between the pendant furan moiety and the aluminum center. F.A. Vengoechea-Gómez et al. / Synthesis and characterization of new types of aluminum and gallium complexesScheme 1. Bifunctional catalysts (ii-iii) and ligand (iv) previously reported.

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“…The Heravi group developed the synthesis of 2‐aryl‐1‐ arylmethyl‐benzimidazoles in good yields by the reaction of o ‐phenylenediamine derivatives with various aromatic aldehydes in the presence of ferric perchlorate, without use of solvent at ambient temperature. The reported method tolerates several functional groups such as methyl, methoxy, nitro, and halogroups 68…”

Section: Sustainable Methodsmentioning

confidence: 99%

Developments Towards Regioselective Synthesis of 1,2‐Disubstituted Benzimidazoles

Carvalho

Fernandes

Marques

2011

Chemistry A European J

141

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1,2-Disubstituted benzimidazoles play an important role in several areas and particularly as drug discovery targets. Herein, several methods to assemble these structures are reviewed, from the classical approaches to the more recently developed metal-catalyzed intramolecular amination process, the cascade arylamination/condensation reaction and polymer-supported benzimidazole assembly under microwave conditions.

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Solventless synthesis of 2-aryl-1-arylmethyl-1H-1,3-benzimidazoles catalyzed by Fe(ClO4)3 at room temperature

Cited by 33 publications

References 42 publications

Selective Synthesis of 2‐Aryl‐1‐benzylated‐1H‐benzimidazoles

Selective Synthesis of 2‐Aryl‐1‐benzylated‐1H‐benzimidazoles

Synthesis and characterization of new types of aluminum and gallium complexes stabilized by bifunctional ligands

Developments Towards Regioselective Synthesis of 1,2‐Disubstituted Benzimidazoles

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