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.
Synthetic access to 7-CF3-1,4-dihydrobenzo[e][1,2,4]triazin-4-yl radicals containing 4-(6-hydroxyhexyloxy)phenyl, 4-hydroxymethylphenyl or 3,5-bis(hydroxymethyl)phenyl groups at the C(3) position and their conversion to tosylates and phosphates are described. The tosylates were used to obtain disulfides and an azide with good yields. The Blatter radical containing the azido group underwent a copper(I)-catalyzed azide–alkyne cycloaddition with phenylacetylene under mild conditions, giving the [1,2,3]triazole product in 84% yield. This indicates the suitability of the azido derivative for grafting Blatter radical onto other molecular objects via the CuAAC “click” reaction. The presented derivatives are promising for accessing surfaces and macromolecules spin-labeled with the Blatter radical.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.