2-Acylcycloalkane-1,3-diones. Occurrence in nature, biological activity, biogenesis, chemical synthesis

Synthesis of exo- and endocyclic enamino derivatives of 2-(3-arylprop-2-enoyl)cyclohexane-1,3-diones

“…The spectra contained a downfield signal at δ 18.4-18.6 ppm due to intermolecularly chelated proton. Such signal is typical of all cyclic β-triketones, and it appears in a weaker field (by 0.2-0.3 ppm) relative to the corresponding signal of β-triketones I with a saturated acyl side chain [16,17], indicating stronger intramolecular hydrogen bond in 2-(3-arylprop-2-enoyl)cyclohexane-1,3-diones IIa-IIf.…”

“…The position of the latter absorption band was very sensitive to conjugation parameters, and its frequency was lower by 20-30 cm -1 as compared to analogous absorption band in the spectra of 2-alkanoylcyclohexane-1,3-diones [16,17].…”

Chemistry of 2-Acylcycloalkane-1,3-diones

“…Alternatively, thia triketones ( 78 ) have been obtained by the reaction of β-chloro enones ( 80 ) with thiourea followed by alkaline hydrolysis of the intermediate thiuronium salts ( 81 ). Careful treatment of salts such as 81 with 1 equiv of base followed by refluxing in anhydrous methanol provides a way to benzothiazinones ( 82 ), which can also be formed by the direct interaction of enol methyl ethers ( 26 ) with thiourea . In this work some of the chemical properties of thia triketones ( 78 ) have been studied.…”

Utilization of CO2 for the Production of Cyclic β-Triketone Type Insecticides

“…To incorporate CO 2 into the insecticide territory, we attempted to synthesize 2-acylcycloalkane-1,3-dione (cyclic β-triketone) type products with CO 2 , since cyclic β-tricarbonyls are known as the main structural feature of the β-tricarbonyl polyfunctional group that forms a part of the skeleton of many biologically active natural products . In addition, cyclic β-triketones are used widely in herbicides, antibiotics, bactericides, anthelmintics, antimalarials, antidiabetics, and medicine as well as a number of modern plant growth regulators. − When one examines the general structure of cyclic β-triketones (Scheme ), it can be divided into a diketone skeleton and substituents including a carbonyl group in the meta-position, which may be obtained via a carboxyl originating from CO 2 .…”