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Molecules 2016, 21(7), 924; doi:10.3390/molecules21070924

An Expeditious and Greener Synthesis of 2-Aminoimidazoles in Deep Eutectic Solvents

1
Dipartimento di Scienze e Tecnologie Biologiche ed Ambientali, Università del Salento, Prov.le Lecce-Monteroni, Lecce I-73100, Italy
2
Dipartimento di Farmacia-Scienze del Farmaco, Università degli Studi di Bari «Aldo Moro», Consorzio C.I.N.M.P.I.S., Via E. Orabona 4, Bari I-70125, Italy
*
Authors to whom correspondence should be addressed.
Academic Editor: Joaquín García Álvarez
Received: 1 July 2016 / Revised: 11 July 2016 / Accepted: 13 July 2016 / Published: 16 July 2016
(This article belongs to the Special Issue Organic Reaction in Green Solvents)
View Full-Text   |   Download PDF [836 KB, uploaded 16 July 2016]   |  

Abstract

A high-yield one-pot two-step synthesis of 2-aminoimidazoles (2-AI), exploiting an under-air heterocyclodehydration process between α-chloroketones and guanidine derivatives, and using deep eutectic solvents (DESs) as nonconventional, “green” and “innocent” reaction media, has been accomplished successfully. The combination of either glycerol or urea with choline chloride (ChCl) proved to be effective for decreasing the reaction time to about 4–6 h in contrast to the 10–12 h usually required for the same reaction run in toxic and volatile organic solvents and under an argon atmosphere. In addition, the use of the ChCl–urea as a DES also enables the direct isolation of triaryl-substituted 2-AI derivatives by means of a simple work-up procedure consisting in filtration and crystallization, and allows the recycle of the DES mixture. A plausible mechanism highlighting the potential role played by hydrogen bonding catalysis has also been illustrated. View Full-Text
Keywords: 2-aminoimidazoles; deep eutectic solvents; green chemistry; heterocyclization; guanidines; α-chloroketones 2-aminoimidazoles; deep eutectic solvents; green chemistry; heterocyclization; guanidines; α-chloroketones
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Capua, M.; Perrone, S.; Perna, F.M.; Vitale, P.; Troisi, L.; Salomone, A.; Capriati, V. An Expeditious and Greener Synthesis of 2-Aminoimidazoles in Deep Eutectic Solvents. Molecules 2016, 21, 924.

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