Svitlychna N. Synthesis and chemical transformations oxo derivatives of imidazo-, pyrazolo-, 1,2,4-triazolo- and tetrazoloazines

Українська версія

Thesis for the degree of Candidate of Sciences (CSc)

State registration number

0413U004053

Applicant for

Specialization

  • 02.00.03 - Органічна хімія

25-04-2013

Specialized Academic Board

Д 64.051.14

V.N. Karazin Kharkiv National University

Essay

The object of the research is: dihydro and tetrahydro derivatives of pyrrolo[1,2-e]imidazol-5-ones, imidazo[1,5-b]pyridazinones, imidazo[1,5-b]cinnolin-9-ones and 1,2,4-triazolo[1,5-a]pyrimidinones, pyrimidо[1,2-a]benzimidazoles. The purpose of the research is: definition of the formation regularities of partially hydrogenated oxo derivatives of imidazo-, pyrazolo-, 1,2,4-triazolo- and tetrazoloazines in reactions of cyclocondensation of corresponding -amino- or 1,2-diaminoazoles with carbonyl bielectrophyles and their synthetic predecessors, elucidation of the subtle structure peculiarities and chemical properties of received compounds. The methods employed are: organic synthesis; physical chemical and spectral methods of researches (individuality of the compounds was carried out by chromathography in subtle layer; composition of the compounds was defined using element analysis; IR spectroscopy, NMR of great precision, mass spectrometry and X-ray researches were applied for definition of new compounds structure). The theoretical and practical value of the research: the cyclocondensation reactions of 2-amino-4-arylimidazoles, 1,2-diamino-4-phenylimidazole, 5-amino-3-methylpyrazole, 5-amino-4-carbethoxypyrazole, 5-aminopyrazole-4-carbonitrile and aminotetrazole with derivatives of , -unsaturated acids and ketones (аrylmethyliden derivatives of Meldrum's acid and 1,3-cyclohexandiones, methylcinnamates and аrylmethyliden derivatives of malonic acid), and their synthetic predecessors and equivalents were studied too; methods of the synthesis of dihydro and tetrahydroimidazopyridazinones and -cinnolinones, pyrrolo[1,2-e]imidazol-5-ones, pyrazolo[3,4-b]quinolinones and -[5,1-b]quinazolinones, tetrazolo[1,5-a]pyrimidinones which were not described earlier in multicomponent condensations and which are high regioselective were worked out; chemical transformations oxo(hydroxy) derivatives azoloazines in reactions with reagents of dehydratation, alkylation, acylation and oxidation have been investigated. The novelty: preparative procedures of the purposeful synthesis of poorly accessible dihydro and tetrahydro derivatives of pyrrolo[1,2-e]imidazolones, imidazo-, pyrazolo-, triazoloazines and routes of the chemical modification of them have been proposed. Implantation: none. Region of application: synthesis of new potential biologically active compounds, and also for preparation of educational text-books, laboratory and lecture courses for the students of chemical specialities.

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