1,3-Bis(carboxymethyl)imidazolium Chloride as a Sustainable, Recyclable, and Metal-Free Ionic Catalyst for the Biginelli Multicomponent Reaction in Neat Condition

ACS Omega. 2021 Oct 1;6(40):26035-26047. doi: 10.1021/acsomega.1c02976. eCollection 2021 Oct 12.

ABSTRACT

A simple and novel methodology has been developed for the synthesis of 1,3-bis(carboxymethyl)imidazolium chloride [BCMIM][Cl] salt. The ionic salt [BCMIM][Cl] catalyzed the reaction among arylaldehydes; the substituted 1,3-dicarbonyl compounds and urea/thiourea at 80 °C with 5 mol % under neat condition provided the substituted dihydropyrimidin-2(1H)-one/thiones in the synthesis step with yields of up to 96%. In addition, we synthesized the commercially available drug Monastrol by employing this methodology. The new synthesis method employs the benefits of a broad substrate scope, short reaction time, and high atom economy along with low catalyst loading in neat conditions, and is devoid of chromatographic purification. The ionic salt [BCMIM][Cl] was recycled and reused up to six cycles without substantial damage of its catalytic efficiency.

PMID:34660965 | PMC:PMC8515400 | DOI:10.1021/acsomega.1c02976

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