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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 44, 2014 - Issue 17
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Original Articles

Oxidative Coupling of o-Phenylenediamine with Arylmethylamines to Synthesize Aryl-Substituted Benzimidazoles Under Catalyst-Free and Solvent-Free Conditions

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Pages 2520-2528 | Received 22 Jan 2014, Published online: 01 Jul 2014
 

Abstract

Solvent-free oxidative synthesis of benzimidazoles from arylmethylamines and o-phenylenediamine has been achieved under catalyst-free conditions. This reaction can use tert-butyl hydroperoxide (TBHP) as the oxidant, and a wide variety of derivatives were obtained in good yields. The reaction mechanism was proposed and this method provides a direct and practical approach for the preparation of substituted benzimidazoles.

GRAPHICAL ABSTRACT

Notes

a Reaction conditions: A mixture of o-phenylenediamine, benzylamine, and TBHP (70% in H2O) was mixed in a three-necked flask, and then stirred rapidly for several hours. The reaction progress was monitored by TLC.

b Isolated yield.

a Reaction conditions: A mixture of 1 mmol diamine, 1.5 mmol aromatic amine, and 4 mmol TBHP (70% in H2O) was mixed in a three-necked flask, and then stirred rapidiy at 100 °C for several hours. The reaction progress was monitored by TLC.

b Isolated yield.

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