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 …

…, PG Tsoungas, C Potamitis, M Zervou, P Cordopatis

Index: Gardikis, Yiannis; Tsoungas, Petros G.; Potamitis, Constantinos; Zervou, Maria; Cordopatis, Paul Heterocycles, 2011 , vol. 83, # 5 p. 1077 - 1091

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Citation Number: 12

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 (1) H NMR spectra indicate an intramolecular H-bonding engaging phenol OH and the isoxazole ring N atom.