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ACS Omega ; 7(26): 22839-22849, 2022 Jul 05.
Article in English | MEDLINE | ID: mdl-35811927

ABSTRACT

An eco-friendly green bio-organic catalyst and low-cost 3,4-dihydropyrimidin-2(1H)-ones/thione derivatives 4-7 have been synthesized using a high-yield, synthetic method via a one-pot, three-component process between 4-formylphenyl-4-methylbenzenesulfonate (1), thiourea, or urea and ethyl acetoacetate or acetylacetone under microwave irradiation in aqueous media of water and ethanol (3:1 ratio) as a green solvent in the presence of cysteine as a new green bio-organic catalyst. The reaction between compound 1, 4-(carbamothioylhydrazono) methyl]phenyl 4-methyl benzenesulfonate (3c), and ethyl acetoacetate or acetylacetone under the same condition afforded novel pyrimidines. Similarly, compound 1 was allowed to react with a mixture of 4-(carbamothioylhydrazono)methyl]phenyl 4-methyl benzenesulfonate (3c) and ethyl acetoacetate or acetylacetone under the same condition to afford pyrimidine derivatives 8 and 9. Excellent yields (90-98%) were obtained within short reaction times, and problems associated with the toxic solvents used (cost, safety, and pollution) were avoided. The structures of the new compounds were elucidated by elemental and spectral analyses. All compounds were studied using molecular docking, and their antifungal activity was investigated.

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