Description
Main areas of research
Development of synthesis methods, study of the structure, reactivity, stereochemistry and chemical transformation of nitrogen-containing heterocycles: diaziridines, azetidines, 2,4,6,8-tetraazabicyclo [3.3.0] octane-3,7-diones (bicyclic bromides), their type and heteroanalogs, imidazotriazines, 1,2,5-oxadiazoles (furazans) and their N-oxides (furoxans), triazoles, pyrazines, tetrazines, etc.
Creating new, effective, low-stage, environmentally attractive methods for the synthesis of the most promising structures based on the principles of "green chemistry" - carrying out multi-stage processes in one-pot version without isolating intermediate products and using ionic liquids as alternative solvents.
Search for new biologically active compounds (neuro-and cardiotropic, nitric oxide donors, structures with cytoxic, antimicrobial and antifungal activity, etc.) based on the above-mentioned nitrogenous heterocycles.
Creation of new energy-intensive compounds - components of pyrotechnic compositions for various purposes (including compositions for car safety bags), powders, rocket fuels, explosives and other new high-energy materials.
Main results
Two new classes of compounds have been identified - diaziridines and bicyclic bromoureas (BBM) - targeting the central nervous system. One of the representatives of the BBM, 2,4,6,8-tetramethyl-2,4,6,8-tetraazabicyclo [3.3.0] octane-3,7-dione (Mebicar), was introduced into medical practice as an effective daily tranquilizer. Found new types of nitric oxide donors - derivatives of furazano (furoxano) pyridazin-N, N-dioxides and (1,2,3-triazol-1-yl) furasanes.
Simple approaches have been developed to obtain a wide range of functional derivatives of furazan, furoxan, diaziridine, azetidine, and a series of nitrogen-oxygen-containing heterocyclic systems with a unique set of properties has been synthesized.
A number of new rearrangements have been discovered in the series of non-condensed furoxan derivatives (including cascade) and imidazo [4,5-e] thiazolo [3,2-b] -1,2,4-triazines, which made it possible to develop new alternative methods for the synthesis of derivatives 4 -amino-5-nitro-1,2,3-triazoles, 1,2,3-triazole-1-oxides and 1-nitroalkyl substituted 1,2,3-triazoles, 1,2,4-triazoles and 1,2, 4-thiadiazoles and imidazo [4,5-e] thiazolo [2,3-c] -1,2,4-triazines.
Based on diastereoselective cyclocondensation of 4,5-dihydroxy-imidazolidin-2-ones with chiral ureido acids or 1-alkylimidazolones and imidazooxazolonas (R) -1- (1-phenylethyl) urea, we developed preparative methods for the preparation of enantiomerically pure bicycles and tri-syntheses, in accordance with syntheses, and tri-syntheses. .
New directions were discovered for the expansion of the diaziridine cycle in the interaction of trans- and cis-diaziridines with a wide range of dipolarophiles, which formed the basis for the development of new alternative methods for the synthesis of imidazolidin-4-ones, substituted pyrazolines, 1,5-diazabicyclo [3.3.0] octanes and new heterocyclic systems annelated with a triazoline, thiodiazolidine, pyrazolinam and pyrazolium heterocycles, containing as substituents reactive functional groups and pharmacophoric heterocycles.
It has been shown that ionic liquids (IL) are promising, substrate-specific, regenerable solvents, promoters and catalysts for a wide range of classical organic reactions: 1,3-dipolar cycloaddition, Bischler-Napiralski, Henri, Mannich, Schmidt and Chapman rearrangements, nucleophilic aromatic cine-substitution, cycloreversion, etc. On the basis of the conducted research, new, effective, low-stage (intermediates are generated in situ) ecologically attractive methods of obtaining Yenia as well as new and nitrogen-containing heterocyclic structures and a number of aromatic and high-energy compounds.
Four new methods have been developed for the preparation of glycoluril thioanalogs - new pharmacologically active substances with a wide spectrum of action (anxiolytic, cytotoxic, antibacterial), based on two approaches: 1) narrowing of the triazine cycle in imidazo [4,5-e] -1,2,4-triazines under the action of aromatic aldehydes or sodium nitrite in an acidic medium and 2) cyclocondensation of 4,5-dihydroxy-imidazolidin-3-ones (thiones) with monosubstituted ureas or potassium thiocyanate in an acidic medium.
An efficient methodology has been developed for the synthesis of energy-intensive polyazo-secondary secondary amines, derivatives of s-tetrazine and azolo [b] -s-tetrazines, from a single readily available starting compound - 3,6-bis (3,5-dimethylpyrazol-1-yl) -s-tetrazine. In the annelated tetrazine [1,2,4] triazolo [4,3-b] -s-tetrazine formed at the first stage, the dimethylpyrazole cycle is replaced by energy-intensive hetarylamines. The developed methodology is the first example of using the principles of combinatorial chemistry in the field of energy-intensive compounds. More than a hundred compounds of this type have been obtained.
