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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 17
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Original Articles

Green, One-Pot, Solvent-Free Synthesis of 1,2,4,5-Tetrasubstituted Imidazoles Using a Brønsted Acidic Ionic Liquid as Novel and Reusable Catalyst

, , &
Pages 2588-2597 | Received 15 Jun 2009, Published online: 05 Aug 2010
 

Abstract

3-Methyl-1-(4-sulfonic acid)butylimidazolium hydrogen sulfate [(CH2)4SO3HMIM][HSO4], a Brønsted acidic ionic liquid, has been used as an efficient, green, and reusable catalyst for the synthesis of 1,2,4,5-tetrasubstituted imidazoles using benzil, an aromatic aldehyde, and a primary amine in the presence of ammonium acetate under solvent-free conditions. The catalyst could be recycled and reused several times without noticeably decreasing the catalytic activity.

Notes

a 2 mmol benzil, 2 mmol 4-methyl benzaldehyde, 2 mmol aniline, and 2 mmol ammonium acetate at 140 °C.

b Isolated yields.

a Isolated yields.

a Isolated yields.

a All the products were characterized by 1H NMR and IR spectral data and comparision of their melting points with those of authentic samples.

b Isolated yields.

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