Intramolecular cyclization of phenol derivatives bearing aminoquinones using a hypervalent iodine reagent

The hypervalent iodine oxidation of phenol derivatives bearing aminoquinones at the ortho (9) or meta positions (19) in 2,2,2-trifluoroethanol was investigated with the aim of preparing novel antitumor compounds. Azacarbocyclic spirodienone derivatives (13) or phenol derivatives containing the 2,3-dihydro-1H-azepine systems (17, 20) were selectively obtained by the reaction of these phenol derivatives and the hypervalent io dine reagent, phenyliodine(III) bis(trifluoro acetate). The application of this reaction to phenol derivatives bearing aminoquinones (10-12) is also described.