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Synthesis and properties of new derivatives of 1H-imidazole


Author: Şargarovschi Viorica
Degree:doctor of chemistry
Speciality: 02.00.03 - Organic chemistry
Year:2011
Scientific adviser: Fliur Macaev
doctor habilitat, professor, Institute of Chemistry, Academy of Sciences of Moldova
Institution: Institute of Chemistry, Academy of Sciences of Moldova
Scientific council: DH 05-02.00.03
Institute of Chemistry, Academy of Sciences of Moldova

Status

The thesis was presented on the 4 October, 2011
Approved by NCAA on the 22 December, 2011

Abstract

Adobe PDF document0.81 Mb / in romanian

Keywords

organic chemistry, synthesis, 1H-imidazole, ionic liquids, 2-carenes, Econazole and Isoconazol, reactions of Biginelli, Kondakov, Prins, Hofmann and Morita-Baylis-Hillman, antifungus- and antituberculosis activity

Summary

The introduction, 4 chapters, conclusions, the bibliography of 172 references, 105 pages of the main text, 50 pictures and 41 tables. Results are published in 24 scientific papers.

Field of research: organic synthesis.

The aim of the work: the thesis is dedicated to development of effective synthetic routes to a new kind of 1Н- imidazoles and studies their properties.

The research objectives: development of methods of synthesis of new derivatives of 1N-imidazole and to investigation of their reactions for obtaining the practically important substances.

Scientific novelty and originality. It was elaborated a new effective catalytic system as nitrile-functionalized ionic liquid: 4-DMAP for the Morita-Baylis-Hillman reaction. Several kinds of the synthesized carboxy-functionalized imidazolium salt have been employed in order to study the catalytic activity in the Biginelli reaction. When the reaction is carried out solvent-free condition, the expected compounds are isolated in good yields. The Kondakov and Prins reactions of (+)-3-carene has been developed using new functionalized imidazolium salt. This strategy allows for the first time synthesis of the optically active 4-substituted 2-carenes.

Theoretical and application value. The results of this study will expand knowledge in organic chemistry. The synthesis of practically important drugs compounds econazol and isoconazol was carried out for the first time by using the Hofmann’s reaction as a key step of the synthesis. It is shown that addition of methylacrylate to isatines proceeds selectively to form precursors of the substances with anti-HIV activity. It was found that a number of synthesized imidazoles possess a high anti-tuberculosis activity.

The implementation of the scientific results. The results of the thesis can be used as base for further research in the medical chemistry, as well as of the some special courses for students and masters.