Type: Article

Selective synthesis of thiadiazolo-2H-chromen-2-ones and chromeno-thiadiazolo-pyrimidines under thermal conditions and microwave irradiation catalyzed by calixarene-based ionic liquid immobilized on magnetic nanoparticles

Journal: Journal of Molecular Liquids (18733166)Year: 1 March 2024Volume: 397Issue:

Khalili A.Mohammadpoor Baltork I.^aMirkhani V.^aMoghadam M.^aTangestaninejad S.^a Notash B.Sabzyan H.^a

a :University of Isfahan - IRAN(IR) - Isfahan

DOI:10.1016/j.molliq.2024.124118Language: English

Abstract

In this research, a calixarene-based acidic ionic liquid immobilized on Fe3O4 magnetic nanoparticles coated with epoxy-functionalized silica (Calix-AIL-MN) was successfully synthesized and characterized by various spectroscopic and analytical techniques such as FT-IR, VSM, TEM, SEM, EDX, elemental-mapping, TGA, ICP and elemental analysis. This catalytic system showed excellent activity in the selective synthesis of 4-amino-1,3,4-thiadiazolo-2-yl-2H-chromen-2-ones and 6H,7H-chromeno[4,3-d][1,3,4]thiadiazolo[3,2-a]pyrimidines through the one-pot three-component reaction of 4-aminocoumarin, aldehydes, and 2-amino-1,3,4-thiadiazoles under thermal conditions and microwave irradiation, respectively. Short reaction times, high to excellent yields, simple workup, easy recovery and reuse of the catalyst, and solvent-free conditions are the most prominent features of this method, which make it a green and sustainable process for the synthesis of these very important fused heterocycles. © 2024 Elsevier B.V.