Urea–Zinc Chloride Eutectic Mixture-Mediated One-Pot Synthesis of Imidazoles: Efficient and Ecofriendly Access to Trifenagrel

Natalia López Higuera; Diana Peña-Solórzano; Cristian Ochoa-Puentes

doi:10.1055/s-0037-1610679

Synlett, Table of Contents

Synlett 2019; 30(02): 225-229
DOI: 10.1055/s-0037-1610679

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Urea–Zinc Chloride Eutectic Mixture-Mediated One-Pot Synthesis of Imidazoles: Efficient and Ecofriendly Access to Trifenagrel

Natalia López Higuera

,

Diana Peña-Solórzano

,

Cristian Ochoa-Puentes*

Abstract

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Abstract

The low-melting mixture urea–ZnCl₂ was evaluated as a novel reaction medium for the synthesis of imidazoles. The reaction between a dicarbonyl compound, ammonium acetate, and an aromatic aldehyde is efficiently catalyzed by the eutectic solvent, yielding a wide variety of triaryl-1H-imidazoles or 2-aryl-1H-phenanthro[9,10-d]imidazoles in good to excellent yields. In addition, the eutectic solvent was reused in five cycles without loss of its catalytic activity. This protocol was further explored for the synthesis of the drug trifenagrel, giving an excellent yield.

Key words

imidazoles - deep eutectic solvent - multicomponent reaction - trifenagrel - phenanthroimidazoles

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References

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