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Paper | Regular issue | Vol 83, No. 5, 2011, pp.1077-1091
Published online, 10th March, 2011
DOI: 10.3987/COM-11-12162
Xanthones in Heterocyclic Synthesis. An Efficient Route for the Synthesis of C-3 o-Hydroxyaryl Substituted 1,2-Benzisoxazoles and Their N-Oxides, Potential Scaffolds for Angiotensin(II) Antagonist Hybrid Peptides

Yiannis Gardikis, Petros G. Tsoungas,* Constantinos Potamitis, Maria Zervou, and Paul Cordopatis*

*Research & Technology, Ministry of Education, 14-18 Messogeion Ave., Athens, GR-115 10, Greece

Abstract

Regioselective substitution of xanthone and its nucleophilic cleavage allow the synthesis of C-3 o-hydroxyaryl substituted 1,2-benzisoxazoles or their N-oxides by cyclodehydration or oxidative cyclization of their corresponding ketoxime precursors, respectively. Molecular modeling analysis and 1H NMR spectra indicate an intramolecular H-bonding engaging phenol OH and the isoxazole ring N atom.