Kulikov O. Synthesis, structure and properties of 2-aminobenzophenones oximes and their derivatives

Українська версія

Thesis for the degree of Candidate of Sciences (CSc)

State registration number

0405U004409

Applicant for

Specialization

  • 02.00.03 - Органічна хімія

27-10-2005

Specialized Academic Board

Д 41.219.02

Essay

Object of investigation: 2-aminobenzophenones oximes and their derivatives, 16- and 18-membered dibenzodioxatetraazamacroheterocycles (DDТМH). Aim of investigation: development of synthetic methods, investigation of structure, physico-chemical properties and biological activity of 2-aminobenzophenones oximes and their derivatives (6-substituted 1,2-dihydro-4-phenylquinazolines, 16- and 18-membered DDТМH). Methods of investigation and equipment: 1H NMR-, IR-, UV-, luminescent spectroscopy, mass-spectrometry, X-ray and element analysis, pharmacolo-gical screening and organic synthesis. Theoretical results and their novelty: It was found that when acylation of syn-isomers of 2-aminobenzo-phenones oximes by chloroacetylchloride and ?-сhloropropionylchloride in the absence of bases accompanied by the isomerisation, the acylation of oximes with chloroacetylchloride under Shotten-Baumann conditions occurred without change of initial oxime configuration. It was found that syn- and аnti-isomers of 2-aminobenzophenone oximes and their acylated derivatives form intermolecular hydrogen bonds, moreover аnti-isomers form intramolecular H-bond between a proton of the NH-group and the imine nitrogen atom. The 16-and 18-membered macrocycles are formed without configuration change of corresponding 2-aminobenzophenones oximes. Practical results and their novelty: 5-Substituted 2-aminobenzophenones oximes were synthesized. It was found, that syn-isomers of 5-substituted 2-aminobenzophenones oximes and 2,2-dimethyl-1,2-dihydroquinazoline-3-oxides possess antiaggregative activity. Some new compounds from 16-membered DDTMH were prepared. It was found, that 16-membered DDTMH when treated with N-nucleophiles (hydroxylamine, hydrazine, semicarbazide, and thiosemicarbazide) gave corresponding derivatives of 4-phenylquinazoline-2-carbaldehydes (oximes, hydrazones, semicarbazones, and thiosemicar-bazones). The method for the preparation of 18-membered DDTMH has been developed, crystal and molecular structures of one of compounds synthesized have been studied by X-ray analysis. Complexing properties of 16- and 18-membered macrocycles with Eu3+ and Yb3+ ions have been investigated. Subject and the degree of introduction: publications, reports at the scientific conferences, using the results of work in the scientific practice of Scientific Research Institutes of Ukraine. Efficiency of introduction is ensured by the development of the synthetic methods for the preparation of 16- and 18-membered macrocycles and their derivatives. Sphere of use: chemistry.

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