Synthesis, Glucosylation and Polarographic Studies of Benzofused Pyrimidine Derivatives

Abstract

7-Amino-3-methyl-5-(3′-aryl prop-2′-enoyl)-1,2-benzisoxazoles (2a-j) were synthesized by the condensation of 5-acetyl-7-amino-3-methyl-1,2-benzisoxazole (1) with aldehydes. The reaction of products 2a-j with urea produced 7-amino-3-methyl-5-(4′-aryl-2′-pyrimidin-6′-yl)-1,2-benzisoxazole derivatives (3a-j). Glucosylation of 3a-j with 2,3,4,6-tetra-O-acetyl glucuropyranosyl bromide (TAGBr) and tetrabutylammonium bromide (TBAB) gives corresponding glucosylated 7-amino-(β-D-2,3,4,6- tetra-O-acetyl glucopyranosyl)-3-methyl-5-(4′-aryl-2′-pyrimidin-6′-yl)-1,2-benzisoxazoles (4a-j). Glucosylated compounds 4a-j on deacetylation gives target products 7-amino-(β-D-glucopyranosyl)- 3-methyl-5-(4′-aryl-2′-pyrimidin-6′-yl)-1,2-benzisoxazoles (5a-j). Glucosylation and deacetylation reaction carried out by Knenigs-Knorr reaction. All the synthesized products were characterized by elemental analysis, IR, 1H NMR, 13C NMR and mass spectroscopy. The biological and electrochemical activities of all the synthesized compounds were also examined.