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Preparation of new cycloalkenyl sulfo-containing isoxasozole derivatives by ring closing metathesis reactions


Presented V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the National Academy of Sciences of Ukraine

Pavliuk O.V.

 The study of the possibilities of obtaining and synthesis of new practically useful substances from available chemical raw materials is one of the most important tasks of modern synthetic organic chemistry. Olefin metathesis reactions are a modern, unique means of synthesizing complex organic molecules in the hands of scientists, which allows, with the help of metal-carbon catalysts, to redistribute the unsaturated bonds of the carbon skeleton in a new way, with the formation of new unsaturated compounds. This research is devoted to the study of the possibilities of obtaining and developing convenient preparative methods for the synthesis of new cycloalkenyl sulfo-containing derivatives of isoxazole by ring closing metathesis reactions, which may have a number of practically useful properties.
Several methods have been developed for the production of sulfonyl chlorides of the isoxazole series, in particular as a result of the interaction of isoxazole-containing salts of sulfinic acids with phosphorus pentachloride and as a result of oxidative chlorination of the corresponding isoxazole-containing isothiuronium salts 3-aryl-5-aryl alkoxy-aryl) -isoxazolyl-5-yl methanesulfonyl chlorides and 3- (3,5-dichloro-4-alkoxy-aryl)) -isoxazolyl-5-yl methanesulfonyl chlorides, were obtained respectively. The possibility of obtaining a number of 5-arylsulfomethyl-3-aryl-isoxazoles with an active methylene group as a result of the interaction of 5-bromomethyl-3-arylisoxazoles with sodium salts of arylsulfonic acids was considered. Several convenient synthetic strategies for obtaining diamidosulfones of the isoxazole series have been developed and worked out. As a result of the conducted researches, convenient ways of obtaining a number of new diallyl-containing sulfoderivatives of isoxazole - precursors of cycloalkenyl derivatives have been found and worked out. The obtained dialkenyl derivatives are converted into new cyclo- and heterocycloalkenyl isoxazole derivatives by ring closing metathesis reactions with high yields.Thus, as a result of this study, convenient synthetic sequences were found and tested to obtain a wide range of three types of new isoxazole derivatives, such as pyrroline-containing sulfonylamides of aryl isoxazoles, cyclopentane derivatives of arylsulfonyl isoxazole series, aryl isoxazole-containing derivatives of thiadiazepine-1,1- dioxide. The structure of the synthesized compounds was confirmed by elemental analysis, 1H, 13C NMR spectroscopy, and chromato-mass spectrometry. Some of the synthesized diallyl-containing derivatives of the isoxazole series may be promising, as anti-wear and extreme pressure additives to aviation oils based on pentaerythritol ester and synthetic fatty acids. As a result of primary biological tests, compounds with antifungal and antitumor activities have been identified among the synthesized substances.

Number of publications: 6 articles (including 3 - in foreign journals), 1 patent for a utility model, 1 patent for an invention and 14 theses. The total number of publications of the authors is 22.