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
Regioselective substitution of xanthone and its nucleophilic cleavage allow the synthesis of C-3 ohydroxyaryl substituted 1, 2-benzisoxazoles or their V-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. The Japan Institute of Heterocyclic Chemistry.
Gardikis, Yiannis,Tsoungas, Petros G.,Potamitis, Constantinos,Zervou, Maria,Cordopatis, Paul
p. 1077 - 1091
(2011/06/19)
Xanthones in heterocyclic synthesis. An efficient and general route for the synthesis of regioselectively substituted phthalazines
Xanthone undergoes regioselective substitution and nucleophically - triggered ring opening to the corresponding ketone. Hydrazone of the latter oxidatively rearranges to ortho-diacylarenes, which, then, with hydrazine gives regioselectively substituted phthalazines. Molecular modeling analysis and 1HNMR spectra indicate an intramolecular H-bonding engaging phenol OH and phthalazine N-3 atom.
Gardikis, Yiannis,Tsoungas, Petros G.,Potamitis, Constantinos,Pairas, George,Zervou, Maria,Cordopatis, Paul
experimental part
p. 1291 - 1302
(2011/06/27)
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