Affiliation:
1. Department of Chemistry, Jawaharlal Nehru College, Wadi, Nagpur-440023, India
2. Department of Chemistry, Mahatma Jyotiba Phule, Educational Campus, Rashtrasant, Tukadoji Maharaj Nagpur University, Nagpur-440033, India
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.
Publisher
Asian Journal of Chemistry
Cited by
2 articles.
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