Pavliuk O. Synthesis of new cyclo- and heterocycloalkenyl sulfo-containing derivatives of isoxazole by ring closing metathesis reactions

Ring closing metathesis reactions, sulfo-containing isoxazole derivatives. Development of ways of synthesis and production of new, potentially practically useful cyclo- and heterocycloalkenyl sulfo-containing derivatives of isoxazole by ring closing metathesis reactions (RCM). Chemical synthesis, NMR spectroscopy, elemental analysis, mass spectrometry (establishment of the structure of synthesized compounds), thin layer chromatography (qualitative determination of the course of reactions), column chromatography (purification of reaction products from impurities), experimental biological studies, determination of the effect of dialyl-containing additives on dynamic strength of the test oils according to the ASTM D2783 method (GOST 9490-75) on a four ball friction machine. For the first time, a number of new pyrroline sulfo-containing and cyclopentenyl-containing arylsulfone derivatives of arylisoxazoles were synthesized by RCM reactions. Convenient methods for obtaining new N, N'-diallyl derivatives of bis- (arylisoxazolylamido) sulfones have been found and worked out. For the first time, a number of new arylisoxazolyl-containing thiadiazepine-1,1-dioxide derivatives were synthesized by the RCM reaction. Initial theoretical and experimental studies of antifungal and antitumor activity of synthesized compounds were performed, as a result of which promising biologically active substances have been found. The possibilities of using a number of synthesized substances as antiwear additives to synthetic aviation oils were investigated, as a result of which a compound has been found that is 38% more effective than the industrial additive DF-11. A utility model patent has been obtained. The practical significance of the obtained results lies in the development of effective preparative methods for the synthesis of a number of new, potentially practically useful cycloalkenyl and heterocycloalkenyl sulfo-containing derivatives of arylisoxazoles using the final stage of the RCM reaction. Scope: pharmaceutical industry and production of lubricants.