A facile synthesis of new coumarin-3, 4-dihydropyrimidin-2(1H)-ones/thiones dyads. Issue 23 (10th June 2015)

• Record Type: Journal Article
• Authors: Benazzouz, Amina; Makhloufi-Chebli, Malika; Khatir-Hamdi, Nejla; Boutemeur-Khedis, Baya; Silva, Artur M.S.; Hamdi, Maamar
• Is Part Of: Tetrahedron. Volume 71:Issue 23(2015)
• Page Start: 3890
• Page End: 3894
• Publication Date: 2015-06-10
• Subjects: Nitrogen heterocycles -- 3-(Acetoacetyl)coumarins -- 3, 4-Dihydropyrimidinone -- 3, 4-Dihydropyrimidinethione -- Biginelli reaction; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2015.04.028
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A new series of 4-aryl-6-methyl-5-(2-oxo-2 H -chromene-3-carbonyl)-3, 4-dihydropyrimidin-2(1 H )-ones/thiones (DHPMs) have been synthesized through multicomponent Biginelli reactions, involving 3-(acetoacetyl)coumarin derivatives, para -substituted benzaldehydes, and urea/thiourea in refluxing acetonitrile, in the presence of a catalytic amount of sulfuric acid. The structure of all newly synthesized compounds has been established by 2D NMR spectroscopic spectra (HSQC, HMBC, and NOESY), elemental analysis, and mass spectrometry. Graphical abstract: