V. G. Kasradze

Ozonolysis of Unsaturated Carbonyl Compounds and Alcohols

Mechanisms of ozonolysis of unsaturated carbonyl compounds and alcohols were considered, and the effects of the substrate structure and reaction conditions on the product composition were analyzed.

Novel synthesis of Planococcus citri pheromone

An effective method was proposed for synthesizing (+)-cis-1R-acetoxymethyl-3-isopropenyl-2,2-dimethylcyclobutane, a pheromone of the citrus mealybug, based on ozonolysis of verbenone that led in one step to the key synthon 1R,3S-3-acetyl-2,2-dimethylcyclobutanecarboxylic acid.

Synthesis of Biologically Active Substances Based on Phenoxyethanol Derivatives

By reaction of phenoxyethanol with diverse structure acyl chlorides phenoxyethanol esters were synthesized containing in the molecule fragments of undecene acid and also of some ketocarboxylic acids. The latter acids were obtained by ozonation of alkylcyclenes.

Oxidative halogenation of 6-methyluracil

An efficient method has been developed for the preparation of halo derivatives of 6-methyluracil by employing oxidative halogenation. Elemental halogens and potassium halides were used as the halogenating agents, while NaNO3 and H2O2 were used as the oxidizing agents. Iodination of 6-methyl-uracil leads to 5-iodo-6-methyluracil as the single reaction product, while bromination or chlorination lead to 5-halo-6-methyluracil, 5,5-dihalo-6-hydroxy-6-methyl-5,6-dihydrouracil, or their mixture depending on the acidity of the medium and the ratio of the substrate and reagents. Bromination of 5-chloro-6-methyluracil leads to 5-bromo-5-chloro-6-hydroxy-6-methyl-5,6-dihydrouracil, while chlorination of 6-methyl-, 5-bromo-6-methyl-, and 5-chloro-6-methyluracils using gaseous chlorine yields 5,5-dichloro-6-hydroxy-6-methyl-5,6-dihydrouracil.

Insect pheromones and their analogs LIX. A new method for the synthesis of components of the sex pheromones of insects of the genusMalacosoma

A new method has been developed for the synthesis of the main components of the sex pheromones of insects of theMalacasoma genus that is based on the selective transformation of the product of the partial ozonolysis of cyclohexa-1,4-diene — methyl 6-oxohex-4E-enoate.

Ozonolysis of (1R,cis)-4,7,7-Trimethyl-3-oxabicyclo[4.1.0]hept-4-en-2-one

The structure of peroxides forming in ozonolysis of enololactone and their further transformations are determined by the structure of the initial substrate and by effect of solvent used for ozonolysis.

Oxidative transformations of polyprenols

Oxidative transformationsinvolving the hydroxylsand ω-methylsof polyprenolsisolated from birch greenery (7-9 isoprene units in the chain) were used to produce α,ω-diols, diesters, aldehydoalcohols, and hydroxyacids. The products are of interest as potential anti-inflammatory, antiulcer, hepatoprotective, and cardio-active preparations.

Synthesis of aryl-containing isoprenoids from 1,5-dimethylcycloocta-1,5-diene

A procedure has been developed for the synthesis of Pro-Drone homo analogs from the ozonolysis products of 1,5-dimethylcycloocta-1,5-diene and 1,5-dimethylcyclooctene.

Synthesis of dicyclopropanes from 4,7,7-Trimethyl-3-oxabicyclo[4.1.0]hept-4-en-2-one

New optically active dicyclopropanes were synthesized on the basis of transformation products of 4,7,7-trimethyl-3-oxabicyclo[4.1.0]hept-4-en-2-one using dichlorocarbene or sulfoxonium ylide in the key cyclopropanation stages.

Reactions of (1S, 3S)-3-acetoxymethyl-1-(2-acetoxyvinyl)-2,2-dimethylcyclopropane with haloforms under conditions of phase-transfer catalysis

Heating of (1S,3S)-3-acetoxymethyl-1-(2-acetoxyvinyl)-2,2-dimethylcyclopropane with bromoform under phase-transfer catalysis affords dibromocyclopropane viaaddition of dibromocarbene to the double bond. In an analogous reaction with chloroform, the trichloromethyl anion adds to the double bond in the α-position with respect to the acetoxy group.