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A synthetic route to novel 3-substituted-2,1-benzisoxazoles from 5-(2-nitrobenzylidene)(thio)barbiturates
- 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).
- Subjects :
- Barbituric acid
Bicyclic molecule
010405 organic chemistry
General Chemical Engineering
Benzisoxazole
Thio
General Chemistry
010402 general chemistry
Ring (chemistry)
01 natural sciences
0104 chemical sciences
chemistry.chemical_compound
chemistry
Organic chemistry
Organic synthesis
Isoxazole
Xanthine oxidase
Subjects
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