Anthrapyridone syntheses: Electronic effects, part II

CHED 796

Joseph S. Clements, Eva Csuhai, Gerald L. Seebach, and Stephen E. Nybo. Division of Natural Sciences and Mathematics, Transylvania University, 300 North Broadway, Lexington, KY 40508
Anthraquinones and anthrapyridones have many applications as dye materials. A series of anthraquinones are synthesized and converted to the corresponding anthrapyridones by a reaction with diethyl malonate (DEM). A 50-80 nm hypsochromic shift is observed in the ultraviolet-visible spectra as a result of the reaction from the anthraquinone to the anthrapyridone. Utilizing nucleophilic aromatic substitution on bromaminic acid, using amines, such as isopropyl amine, (+-)-1-amino-cis cyclopentane-1,3-dicarboxylic acid, and 2-azabicyclo[2.2.1]hept-5-en-3-one, a variety of anthraquinones were produced, which were then converted into the corresponding anthrapyridones. Some of the anthraquinones do not form the corresponding anthrapyridones. This conversion is investigated to determine whether it is an activation problem or a steric concern.