Detistov O. Bis-heterocyclic systems containing 1,2,4-oxadiazole ring: synthesis and reactivity.

The subject of study - heteryl-1,2,4-oxadiazoles. The aim of this work is to develop a general preparative methods for the synthesis of heterocyclic systems containing 1,2,4-oxadiazole cycle, combined with coumarin, pyrazole, and triazole cycles, as well as the study of the reactivity and properties of substances of this class. Research methods and equipment - organic synthesis, thin-layer chromatography, 1H NMR, 13C NMR, 13C NMR DEPT, 2D NOESY, IR, UV spectroscopy, liquid chromatography-mass spectrometry, elemental analysis, and microbiological screening, chemical glass vessels, refrigerators, electric heating furnaces with magnetic stirring, rotary evaporator. Theoretical and practical results. We propose new convenient methods for synthesis of functionally substituted 1,2,4-oxadiazoles - 5-cyanomethyl-1,2,4-oxadiazoles and 5-acetonyl-1,2,4-oxadiazoles. Using these compounds as starting components, new heterocyclic systems were obtained. The antimicrobial and fungicidal activities of 3-[1,2,4-oxadiazol-5-yl]coumarins were studied. 124 undescribed in the literature compounds were synthesized and characterized. Novelty: 2-imino-3-[1,2,4-oxadiazol-5(3)-yl]coumarins have been obtained and characterized for the first time; a new efficient method for the synthesis of derivatives of 5-(5-amino-1H-4-pyrazolyl)-[1,2,4] oxadiazoles has been developed; the synthesis of triazoles by Dimroth reaction was tested on 5-cyanomethyl-1,2,4-oxadiazole and 5-acetone-1,2,4-oxadiazole for the first time. Degree of implementation: results of the thesis is used in carrying out R & D budget of Organic Chemistry and in a writing of diploma theses of students of Chemical Department of the V.N. Karazin Kharkiv National University. Scope (area) of use: organic synthesis, development of new pharmaceuticals (based on data from microbiological screening of 3-[1,2,4-oxadiazol-5-yl]coumarins).