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

Authors :
Paulo Almeida
Maria João Romão
Sónia Barroso
Samuel Silvestre
João L. Serrano
Eunice Cavalheiro
Source :
Comptes Rendus Chimie. 20:990-995
Publication Year :
2017
Publisher :
Elsevier BV, 2017.

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).

Details

ISSN :
16310748
Volume :
20
Database :
OpenAIRE
Journal :
Comptes Rendus Chimie
Accession number :
edsair.doi...........ef9079209aa0fcf26420407f14204d86
Full Text :
https://doi.org/10.1016/j.crci.2017.10.002