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Synthesis and Biological activities of 1,2-Benzisoxazoles and their N-Glucosides

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Author Affiliations

  • 1Department of Chemistry, Mahatma Jyotiba Phule, Educational Campus, Rashtrasant Tukadoji Maharaj Nagpur University, Nagpur-440 033, INDIA
  • 2Department of Chemistry, Jawaharlal Nehru College, Wadi, Nagpur-440 023, INDIA

Res.J.chem.sci., Volume 6, Issue (1), Pages 61-68, January,18 (2016)

Abstract

2-oximinoacetyl-4-acetyl phenol 2 was prepared by the interaction of 2,4-diacetyl phenol 1 with hydroxylamine hydrochloride using suitable solvent. Cyclization of product 2 with acetic anhydride using N,N-Dimethylformamide afforded 3-methyl-5-acetyl-1,2-benzisoxazole 3. Nitration of compound 3 with nitrating mixture produces 3-methyl-5-acetyl-7-nitro-1,2-benzisoxazole 4. 3-Methyl-5-acetyl-7-amine-1,2-benzisoxazole 5 was prepared by the reduction of product 4 using tin and hydrochloric acid. Different 3-methyl-5-(3¨-aryl prop-2¨-enoyl)-7-amine-1,2-benzisoxazoles 6a-j have been synthesized by the interaction of appropriate 3-methyl-5-acetyl-7-amine-1,2-benzisoxazole 5 with different aromatic aldehydes using piperidine. The reaction of 3-methyl-5-(3-aryl prop-2-enoyl)-7-amine-1,2-benzisoxazoles 6a-j with hydrazine hydrate in alcoholic KOH to obtained 3-methyl-5-(3-aryl-1H- pyrazol-5¨-yl)-7-amine-1,2-benzisoxazoles 7a-j. Condensation of tetra-O-acetyl-±-D-glucopyranosyl bromide with compounds 7a-j furnishes 3-methyl-5-(3¨-aryl-1H-pyrazol-5¨-yl)-7-amine-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1,2-benzisoxazoles 8a-j which on deprotection to get 3-methyl-5-(3¨-aryl-1H- pyrazol-5¨-yl)-7-amine-(β-D-glucopyranosyl)-1,2-benzisoxazoles 9a-j. The synthesized compounds were characterized on the basis of IR, 1H NMR, 13C NMR and Mass Spectroscopy, Elemental analysis, TLC, chemical properties and Polarographic studies. All compounds have been screened for antimicrobial activities and some compounds show potent activities.

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