C-acylation of 5-trifluoromethyl-1,3-cyclohexanedione with substituted unactivated carboxylic acids and benzoyl chlorides
The cyclic â-triketone moiety is part of the skeleton of diverse natural compounds with a wide range of biological activities, including antibiotic, antibacterial, and anticancer properties. Moreover, several patents describe herbicides containing the â- triketone framework, such as 2-[2-nitro-4-(triflouromethyl)benzoyl]-1,3- cyclohexanedione (NTBC) and commercially available sethoxydim and trialkoxydim herbicides. Sethoxydim is a commercially available cyclohexanedione class herbicides, that shows moderate inhibition of 4-hydroxyphenylpyruvate Dioxygenase (4-HPPD), a key enzyme in the biosynthesis of tocopherol and plastoquinones in plants. In line with our interest in the chemistry of cyclic â-triketone, we reported the synthesis of 5- trifluoromethyl-1,3-cyclohexanedione in a previous publication. The long-term goal of this study is to develop a facile route to novel trifluoromethylated cyclic triketones as potential inhibitors of 4-HPPD. The primary objectives are the synthesis and characterization of fluorinated cyclic triketones from substituted benzoyl chlorides and unactivated carboxylic acids. In this research, we successfully synthesized and confirmed the structures of 10 novel fluorinated cyclic triketones.
Shondra N Gipson,
"C-acylation of 5-trifluoromethyl-1,3-cyclohexanedione with substituted unactivated carboxylic acids and benzoyl chlorides"
ETD Collection for Tennessee State University.