One-Pot Efficient Synthesis of 2-Aryl-1-arylmethyl-1H-benzimidazoles and 2,4,5-Triaryl-1H-imidazoles Using Oxalic Acid Catalyst

Nagnnath D. Kokare; Jaiprakash N. Sangshetti; Devanand B. Shinde

doi:10.1055/s-2007-983872

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Synthesis 2007(18): 2829-2834
DOI: 10.1055/s-2007-983872

PAPER

One-Pot Efficient Synthesis of 2-Aryl-1-arylmethyl-1H-benzimidazoles and 2,4,5-Triaryl-1H-imidazoles Using Oxalic Acid Catalyst

Nagnnath D. Kokare^a,b, Jaiprakash N. Sangshetti^a, Devanand B. Shinde^a
^a Department of Chemical Technology, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad-431004 (MS), India
^b New Drug Discovery, Wockhardt Research Centre, Aurangabad-431210 (MS), India
e-Mail: dbschemtech@hotmail.com;

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Publication History

Received 12 March 2007
Publication Date:
29 August 2007 (online)

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Abstract

Oxalic acid was found to be a versatile catalyst for the synthesis of 2-aryl-1-arylmethyl-1H-benzimidazoles and 2-aryl-4,5-diphenyl-1H-imidazoles in moderate to excellent isolated yields. 2-Aryl-1-arylmethyl-1H-benzimidazoles were efficiently synthesized from o-phenylenediamine and various substituted aldehydes using 10 mol% oxalic acid. 2-Aryl-4,5-diphenyl-1H-imidazoles were synthesized from benzil or benzoin, ammonium acetate, and aromatic aldehydes. The advantages of this method are the use of an inexpensive and readily available catalyst, easy workup, and improved yields, and the use of an ethanol-water solvent that is considered to be relatively environmentally benign.

Key words

oxalic acid - 2-aryl-1-arylmethyl-1H-benzimidazole - 2,4,5-triaryl-1H-imidazole - benzoin - benzil - aromatic aldehydes

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