Functional Planar Blatter Radical through Pschorr-Type Cyclization

Abstract

A series of functional 2-phenyl-3H-[1,2,4]triazino[5,6,1-kl]phenoxazin-3-yl (planar Blatter) radicals containing CO2Me, CN, and NO2 groups at the C(10) position and 2-phenyl-3H-pyrido[3,2-b][1,2,4]triazino[1,4]benzoxazin-3-yl have been obtained in yields of 40–80% by using the Pschorr-type cyclization and characterized by spectroscopic (ultraviolet–visible and electron paramagnetic resonance), electrochemical, and density functional theory methods. Two of these groups, CO2Me and NO2, have been transformed into CO2H and NH2, respectively, and conjugated with amino acids. One of the derivatives was analyzed by single-crystal X-ray diffraction methods.