Description
Main results (2007-2012)
In the Laboratory of Heterocyclic Compounds (LGS), studies are being carried out related to the production of photoactive substances for optical memory. Compounds based on chromones that undergo rearrangement under UV irradiation with the formation of fluorescent products were created. The process is used to obtain photosensitive media for archival optical memory.
Scheme 1
Methods of synthesis have been developed and the photochemical properties of an extensive range of reversible photochromic compounds have been studied based on thermally irreversible digetaryl ethenes containing thiophene and benzothiophene cycles linked by cyclopentenic, perfluorocyclopentene, maleimide, and other heterocyclic bridges.
Scheme 2
Digetarilethenes are synthesized with sulfur-containing functions, which ensure their effective binding with the nanoparticles of noble metals.
An optical device has been created on the basis of chromones and digetaryletenes, which provides layer-by-layer recording, erasing, storing, and reproducing rewritable and archival optical information in multilayer (up to 10 layers) recording medium.
The interaction of thiophene-based fulgides with various amines yielded a wide range of different fulgimides, among which are fluorescent substances, their photochromic properties were studied and it was shown that these products are close in reactivity and photochromic properties to digetril ethenes and can be used in optical memory devices.
Scheme 3
A systematic study of the Fisher reaction for thiophene derivatives made it possible to synthesize previously practically inaccessible thienopyrroles and thienopyrrolenines, on the basis of which a new type of unique photochromic spiropyrans, spirooxazines and merocyanine dyes was created.
Scheme 4
The study of the S-functionalization of organic compounds by elemental sulfur was carried out, which made it possible to significantly expand the possibilities of heterocyclic synthesis based on simple and available starting materials. Methods have been developed for the synthesis of a wide range of monothioxamides, oxamic acid thiohydrazides, as well as their derivatives with aromatic and heteroaromatic fragments, on the basis of which various antibacterial compounds have been obtained, including biologically active, low-toxic substances that inhibit type III secretion system in pathogenic bacteria.
Scheme 5
An approach to the synthesis of new condensed heterocyclic systems containing a dihydropyridinone moiety based on three-component condensation of the corresponding amino heterocycles with aldehydes and Meldrum acid has been developed. Based on the calculations performed using the PASS program for synthesized dihydropyridines, their psychotropic, antineurotic, nootropic and antipsychotic activities were predicted.
Scheme 6
The methods of synthesis at atmospheric and high pressure (10–14 kbar) of derivatives of nitrogen-containing aromatic heterocycles — furazan, furoxan, 1,2,4, and 1,3,4-oxadiazoles, tetrazole, etc. — have been developed, on the basis of which energy-intensive polyazone products were obtained . The reactions of 1,3-dipolar cycloaddition were investigated, original methods for the synthesis of stable aromatic nitrile oxides were created, which formed the basis of the pioneering, environmentally friendly technology of low-temperature vulcanization of rubbers, which has found practical application both in Russia and abroad.
Scheme 7
The laboratory has extensive experience in the synthesis of additives for the tire industry. A domestic technology has been developed for the preparation of the antistorble drug SANTOGARD PVI, and a wide range of sulfenimides has been obtained.
Scheme 8
LGS IOC RAS successfully cooperates with the largest companies in the world, such as MICHELIN, DOW CHEMICAL, INTEL, DUPON, SAMSUNG, LANXESS, etc.
