An 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-1 H -azepine systems ( 17, 20 ) were selectively obtained by the reaction of these phenol derivatives and the hypervalent iodine reagent, phenyliodine(III) bis(trifluoroacetate). The application of this reaction to phenol derivatives bearing aminoquinones ( 10 − 12 ) is also described.