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Paper | Regular issue | Vol 83, No. 6, 2011, pp.1291-1302
Published online, 1st April, 2011
DOI: 10.3987/COM-11-12168
Xanthones in Heterocyclic Synthesis. An Efficient and General Route for the Synthesis of Regioselectively Substituted Phthalazines

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

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

Abstract

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 1H NMR spectra indicate and intramolecular H-bonding engaging phenol OH and phthalazine N-3 atom.