A synthetic route to novel 3-substituted-2,1-benzisoxazoles from 5-(2-nitrobenzylidene)(thio)barbiturates

João L. Serrano, Eunice Cavalheiro, Sónia Barroso, Maria J. Romão, Samuel Silvestre, Paulo Almeida

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

2,1-Benzisoxazoles, also called anthranils, are one of the two types of aromatic bicyclic heterocycles having a benzene ring fused with an isoxazole, which are particularly recognized as valuable intermediates in organic synthesis. Nevertheless several methods can be found in the literature to prepare 2,1-benzisoxazoles, we herein report a new, efficient, simple, mild, and alternative procedure to prepare 3-substituted-2,1-benzisoxazoles from 5-(2-nitrobenzylidene)barbiturates in moderate to good yields (51–82%). All the novel benzisoxazoles showed spectral data fully consistent with the assigned structures, which were unequivocally confirmed by single crystal X-ray analysis. A possible mechanism of the reaction is proposed. In addition, a screening of the bioactivity of these benzisoxazoles as xanthine oxidase inhibitors, antioxidants, and cytotoxic compounds was performed. The benzisoxazole formed from barbituric acid revealed moderate xanthine oxidase inhibitory effects (IC50 = 22.10 μM).

Original languageEnglish
Pages (from-to)990-995
Number of pages6
JournalComptes Rendus Chimie
Volume20
Issue number11-12
DOIs
Publication statusPublished - 1 Nov 2017

Keywords

  • 2,1-Benzisoxazoles
  • Anthranils
  • Barbiturates
  • Single crystal X-ray
  • Xanthine oxidase inhibition

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