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Microwave-Assisted Synthesis of N-Tetra-O-Acetyl-β-DGlucopyranosyl- N'-(4',6'-Diarylpyrimidine-2'-yl)thioureas
Published: 30 October 2009 by MDPI in The 13th International Electronic Conference on Synthetic Organic Chemistry session Symposium on Microwave Assisted Synthesis
Abstract: Some 2-amino-4,6-diarylpyrimidines 2 have been prepared from substituted benzylideneacetophenones and guanidine hydrochloride in presence of alkali by conventional heating in alcoholic medium and microwave heating in solvent-free conditions. N-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-N'-(4',6'-diarylpyrimidine-2'-yl)thioureas 4 have been synthesized by reaction of per-O-acetylated glucopyranosyl isothiocyanate 1 and substituted 2-amino-4,6-diarylpyrimidines 2. Two different methods have been used, namely refluxing in anhydrous dioxane and solvent-free microwave-assisted coupling. The second procedure afforded higher yields in much shorter reaction times. The compounds 2 and 4 were tested for their antibacterial and antifungal activities in vitro against Staphylococcus epidermidis, Enterobacter aerogenes and Candida albicans by disc diffusion method.
Keywords: pyrimidine; glucopyranosyl thiourea; glucopyranosyl isothiocyanate; microwaveassisted method