Zamigajlo L. Enonic systems are based on heterocyclic CH-acids in reactions with ureas, thioureas and 1,2-diaminobenzoles

Українська версія

Thesis for the degree of Candidate of Sciences (CSc)

State registration number

0409U002843

Applicant for

Specialization

  • 02.00.03 - Органічна хімія

12-06-2009

Specialized Academic Board

Д 64.051.14

V.N. Karazin Kharkiv National University

Essay

Investigation objects: heterocyclic and alicyclic CH-acids (1,3-dimethylbarbituric and thiobarbituric acids, 4-hydroxycoumarine, dimedone), arylglioxals, ureas, thioureas and thioamides. Objectives: synthesis of condensed and uncondensed of heterocyclic systems (pyrimidinones, imidazolin-2-ones, thiazoles) are based on new enonic systems made from arylglioxals and cyclic beta-dicarbonyl compounds. Methods: organic synthesis, NMR 1Н and 13С, IR-, UV-spectroscopies, mass-spectrometry, X-ray analysis, thin layer chromatography, elemental analysis, virtual biological screening (program PASS). In work were developed and described the methods of synthesis of new enonic systems at involvement of 1,3-dimethylbarbituric or thiobarbituric acids and arylglioxals, their reactivity in relation to ureas, thioureas, thiamides of acids and 1,2-phenylenediamines are researched. Simple paths of the formation of spiropyrimidinones, imidazolin-2-ones, the 2-substituted thiazoles in conditions of the one-pot condensation were proposed. The common character of three-component condensation of CH acids, arylglioxals, ureas, thioureas or thiamides with formation of imidazolin-2-ones and thiazoles was confirmed also on an example of 4-hydroxycoumarine and dimedone. It was studied the regioselectivity of interactions of enonic systems with binucleophilic reagents depending on a structure of nucleophilic agent. Interactions an aroyl-bis-(4-hydroxycoumarinyl-3)methanes with 1,2-phenylenediamines in the various solvents were researched. It was received and described more than 100 new compounds.

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