Nikishin O. 4,4-Disubstituted functionalized pyridinechalcogenones: synthesis, structure and properties

Українська версія

Thesis for the degree of Candidate of Sciences (CSc)

State registration number

0412U000814

Applicant for

Specialization

  • 02.00.03 - Органічна хімія

15-03-2012

Specialized Academic Board

Д 64.051.14

V.N. Karazin Kharkiv National University

Essay

Investigation objects: 4,4-disubstituted functionalized pirydynhalkohenony and their derivatives. Aim: Synthesis of 4,4-disubstituted functionalized pirydynhalkohenoniv based activated olefins and CH-acids by the reaction of Michael, establishing the structure of the obtained compounds and study their properties. Methods and apparatus: synthesis, physico-chemical analysis involving IR, 1H NMR spectroscopy, NMR 13 C spectroscopy, mass spectrometry, elemental and X-ray analysis, thin layer chromatography, virtual biological screening using a computer program PASS (Prediction of Activity Spectra for Substances) and biological screening. Theoretical and practical results: developed convenient preparative methods of synthesis of previously unknown 4,4-disubstituted partially hydrogenated pirydynhalkohenoniv, based on these derivatives obtained selenazolo [3,2-a] pyridine, thiazolo [3,2-a] pyridines and pyrido [3,2-e] [1,3] thiazine; increased availability of synthetic 4,4-disubstituted pirydynhalkohenoniv - potentially bioactive compounds, the results of biological screening of the compounds obtained have shown antioxidant, antibacterial and fungicidal properties. Novelty: studied methods of synthesis of 4,4-disubstituted functionalized pirydynhalkohenoniv by Michael reaction and possible ways of further chemical transformations. It is possible to develop new, regioselectively, simple and convenient methods for synthesis of functionally substituted, potentially bioactive partially hydrogenated 4,4-disubstituted pirydynhalkohenoniv and their derivatives, containing the third position karbonitrylnyy, amide, thioamide, or etoksykarbonilnyy thiazole fragments. It is proved that dytioamid unlike monotiodiamidu malonic acid can be used as bildynh-block for the synthesis of 4,4-disubstituted pirydynhalkohenoniv with thioamide fragment in the third position due to elimination of hydrogen sulfide. Zaprovanovani efficient methods of synthesis of previously unknown obtained on a "Domino" and 1-ethyl-5 ,5-dimethyl-3 ,7-diokso-1 ,2-diazepanu based ethyl ester izopropilidentsianootstovoyi acid and its hydrazides. Thanks to its chemical transformations of the obtained compounds revealed their basic nucleophilic (sulfur atom and amide nitrogen atom) and electrophilic (tsianohruppy in regulations 3.5 and C5-H position) reaction centers. In a reaction Mannich 's first received Conducted pre-clinical testing of the synthesized compounds and found that some of them have antibacterial, fungicidal and antioxidant activity. Degree of implementation: None. Field (field) use: Laboratory and Department of various educational and research units which conducts research on topics close to facilities and research centers to identify and study of biologically active compounds.

Files

Similar theses