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The reaction of 2-chloropyridine-3,4-dicarbonitrile with anilines in propan-2-ol in the presence of N,N- diisopropylethylamine (DIPEA) in a sealed vial at 120°С involves the nucleophilic substitution of chlorine and yields 2-(arylamino)pyridin-3,4-dicarbonitriles.

The article considers possibilities for increasing competitiveness of Russian industrial enterprises during the development of resource effective industrial policy. The authors discuss the meaning and interpretation of “sustainable development” and “competitiveness” used in national and international scientific publications. The article traces current trends in the external environment that can contribute to organization's competitive advantages or cause the stability loss. The most significant changes include: the strengthening of industrial policy at national and international levels; broadening the understanding of essence and geographic scope of regulation based on the principles of best available techniques; promoting resource efficient and low-carbon technologies and formulating new international marketing segment for such technologies; establishing approaches for circular economy and links to resource efficient and low-carbon development; developing responsible investment system supporting activities related to meeting sustainable development goals.The authors analyse the basic principles of Environment Social Governance (ESG) and Business Charter for Sustainable Development and demonstrate their impact on the development of new competition rules.The paper presents results of case studies carried out in pulp and paper production and mining industry: environmental and technological modernizationprojects of JSC “Kovdor Mining and Benefication Plant” and JSC “Mondi Syktyvkar” and compares these projects with theESG investment principles. The procedure for excluding Russian installations from the list of environmental “hot spots” of the Barents Euro-Arctic Region is analysed and project assessment results meeting requirements of Best Available Techniques and responsible investment are considered. The paper concludes with the statement that in order to increase the level of international competitiveness of Russian industries it is necessary to take into account sustainable development principles and ESG principles while developing environmental and technological modernization programmes of Russian enterprises.

Heating of 2-halopyridine-3,4-dicarboxylic acids in propionic anhydride led to the formation of 4-halofuro[3,4-c]pyridine-1,3-diones as a result of intramolecular dehydration of the vicinal carboxy groups. The subsequent reduction of 4-halofuro[3,4-c]pyridine-1,3-diones with sodium tetrahydridoborate in THF at room temperature afforded 4-halofuro[3,4-c]pyridin-3(1H)-ones as the major products.

The goal of our work is to develop a synthesis of tetracyanoethylene suitable for scaling and to design a technological scheme of the process based on it. To achieve this goal, a tetracyanoethylene synthesis method was originally developed, which consists of the following stages: obtaining sodium cyanodithioformate based on carbon disulfide and sodium cyanide using N, N-dimethylformamide as a solvent; obtaining tetracyano-1,4-dithiine by treating sodium cyanodithioformate with chlorine; obtaining tetracyanoethylene from tetracyano-1,4-dithiine by sequential interaction with sodium cyanide and chlorine. The developed method was tested in the laboratory, where it showed its suitability. Therefore, further on the base of this method, a technological scheme of the process was designed. A description of the scheme and the necessary sequence of operations are compiled. The interaction takes place in the reactors R-1, R-2, R-3. Pumps N-1–4 provided the pumping the reaction mass. Also, in the technological scheme there is an F-1 Nutsche filter for separation of the suspension. To isolate and purify the obtained tetracyanoethylene, an I-1 vacuum evaporator and a SA-1 sublimation apparatus are used. The necessary equipment was selected for the technological scheme: Р-1 reactor made of Teflon with a volume of 200 l with a stirrer and a jacket; two reactors Р-2 and Р-3 made of glass with a volume of 200 l with a stirrer and a jacket; Ф-1 Nutsche filter made of thick-walled polypropylene pipes; sublimation apparatus CA-1 continuous. The selection of the main and auxiliary equipment was carried out on the base of the chemical and physico-chemical characteristics of the reagents, technological conditions and the characteristics of the process. This method of obtaining compares favorably with the use of simple and cheap raw materials common in the chemical industry and the use of standard processing equipment.

A series of negative T-type nitrile-rich photochromes containing a hydroxytricyanopyrrole acceptor was synthesized. It was shown that thermal stability of the photoinduced form could be tuned by the replacement of a substituent in para-position to OH-group as well as by the change of a solvent. Ethanol solutions of the synthesized compounds showed significantly shorter half-lives of the reverse dark (thermal) reaction in comparison with solutions in acetonitrile.

Representatives of negative photochromes containing a nitro-substituted 2-vinylphenolic fragment and a tricyanofuran (TCF) acceptor were synthesized. An efficient “turn-off” fluorescence photoswitching with full reversibility was shown for these compounds due to the negative photochromic transformation under irradiation by visible light. The obtained result reveals a new direction in the investigation of fluorescence photoswitching because of the great potential for structural variability of insufficiently studied nitrile-rich photochromes.

The reaction of 4-halo-3-hydroxyfuro[3,4-c]pyridin-1(3H)-ones with acyclic and alicyclic secondary amines in ethyl acetate afforded the corresponding 3-(dialkylamino)-4-halofuro[3,4-c]pyridin-1(3H)-ones in a few minutes.

Previously unknown 3-R-sulfanyl-5-amino-1-phenyl-1H-pyrazole-4-carbonitriles were synthesized by reactions of 2-[bis(alkylsulfanyl)methylidene]malononitriles with phenylhydrazine. A similar reaction with 2-(1,3-dithiolan-2-ylidene)malononitrile afforded 3,3′-{disulfanediylbis[(ethane-2,1-diyl)sulfanediyl]}bis-(5-amino-1-phenyl-1H-pyrazol-4-carbonitrile).

4-Halo-3-hydroxyfuro[3,4-c]pyridin-1(3H)-ones reacted with morpholine and thiomorpholine in ethyl acetate to give in a few minutes 3-(morpholin-4-yl)- and 3-(thiomorpholin-4-yl)-substituted 4-halofuro­[3,4-c]pyridin-1(3H)-ones.

The article discusses a range of economic issues related to the efficient use of the industrial potential of coastal territories (by the example of the Murmansk region) in the development of shelf deposits. A comprehensive analysis of the industrial complex and an objective assessment of conditions for the development of the oil and gas industry in the Murmansk region are given. Considerable attention is paid to the formation of organizational and economic mechanisms for using the industrial potential of regional enterprises in the implementation of oil and gas and large industrial projects in the territory of a new producing area.

The reaction of 4-halo-3-hydroxyfuro[3,4-c]pyridin-1(3H)-ones with propan-2-ol leads to the formation of 4-halo-3-isopropoxyfuro[3,4-c]pyridin-1(3H)-ones. The reaction takes place in the presence of sulfuric acid and 3 A molecular sieves.

The approach to novel group of donor-acceptor chromophores exhibiting solid-state fluorescence based on the reaction of hydroxytricyanopyrrole (HTCP) acceptor with methoxybenzaldehydes has been developed. The presence of a hydroxyl group in the structure of synthesized chromophores allows functionalizing them and tuning their fluorescent properties, varying maxima of emission in a range of 518–617 nm. The developed method is of interest as it is a promising approach to a new group of fluorescent push-pull D-π-A chromophores, which are functionalized analogues of known chromophores based on the tricyanofuran (TCF) acceptor.

One of the major challenges of the modern world is the problem of global warming, the solution of which requires the implementation of a set of strategic projects in the field of transition of the energy sector to the path of environmentally balanced development. One of the ways to implement this transition is the development of technologies for capturing and storage of technogenic carbon dioxide, which is recognized as the main one of greenhouse gases. At the same time, in the Russian context, the most expedient is the implementation of technological chains for capturing and storing CO 2 which are aimed at enhanced oil recovery, the effectiveness of which has been proven by world practice. Implementation of these projects requires consolidation of efforts of many parties, including government agencies, enterprises-issuers (power generating facilities and energy-intensive industry), oil-producing enterprises, non-state environmental organizations, media and public. World practice has many examples when uncoordinated actions of one of the stakeholders led to the closure of such a project, and therefore it is necessary to develop a mechanism of interaction between them, taking into account the specifics of Russian conditions. One of the least studied and controversial aspects of this interaction is to involve the public in the implementation of national carbon intensity programs and the local population in the implementation of a specific project. Research in this field has been conducted in the world over the past 14 years, which allowed the current research base to be used to develop fundamental principles for the development and promotion of CO 2 capture and storage technologies in Russia. Key factors affecting the perception of such projects by public were also analyzed and systematized. The research identified the main arguments for and against the development of CO 2 capture and storage technologies. The analysis made it possible to formulate key principles that should be considered when developing a strategy for the development of these technologies in Russia.

An approach to the synthesis of novel group of negative photochromes has been developed based on the interaction of the tricycanofuran TCF or hydroxytricyanopyrrole HTCP acceptors with methoxy-substituted 2-hydroxybenzaldehydes in ethanol in the presence of ammonium acetate. An essential part of the obtained photochromes is a combination of a phenol fragment and a butadienetricarbonitrile BDTC acceptor connected via a vinylene bridge. The synthesized compounds are sensitive to visible light T-type photochromes. A transformation degree of the initial form, as well as the rate of the reverse dark reaction, can be varied by changing both the position of a methoxy group at aromatic ring and the type of the heterocycle with the BDTC fragment.

Various negative photochromes containing a nitrile-rich acceptor with tunable absorption properties and thermal stability of the photo-induced form were synthesized and characterized. High photoswitching contrast due to the contribution of an intensely colored quinoid form of the chromophores of this series was shown for the first time. The obtained results discovered a new direction in the investigation of negative photochromes.

The first representatives of D–π–A chromophores containing a hydroxytricyanopyrrole (HTCP) acceptor and N,N-disubstituted aminophenyl donor were synthesized. The obtained molecules include reactive NH- and OH-fragments allowing the photophysical properties of the chromophores to be tuned, which is not possible for the well-known chromophores of the tricyanofuran (TCF) and tricyanopyrrole (TCP) series. The absorption properties of the synthesized HTCP-chromophores with a p-aminophenyl electron donor substituent were thoroughly studied.

Two new approaches to the synthesis of functionalized pyridoxine derivatives with hydroxymethyl groups at positions 3 and 4 of the pyridine ring have been implemented based on the transformations of 2-halopyridine-3,4-dicarbonitriles. The first path involves obtaining target compounds with a halogen atom in the 2-position of pyridine by reduction of intermediate pyridine-3,4-dicarboxylates with sodium borohydride. The second approach is based on the reduction of annelated furo[3,4-c]pyridin-3(1H)-ones and allows obtaining both 2-halogen- and 2-alkylamino-substituted pyridoxine derivatives.

Synthetic approaches for modification of negative photochromes of hydroxytricyanopyrrole (HTCP) series were described for the first time. The first and fifth positions of the pyrrole ring were directly functionalized but hydroxyl group of the 2-vinyl-phenol fragment and the butadienetricarbonitrile (BDTC) moiety, which are necessary for the photochromic reaction were untouched. These results are the starting point for wide research in the field of directed synthesis of nitrile rich negative photochromes with tunable physicochemical characteristics.

An unusual example of the selective hydrolysis of a cyano group to the corresponding carboxyl group under mild reaction conditions in the presence of a carboxamide group is reported. The reaction resulted in the formation of a rare combination of vicinal carboxamide and carboxyl groups on a pyridone ring. The structure of the synthesized products was thoroughly studied using one- and two-dimensional NMR experiments and the reaction pathway was monitored fluorometrically.

The reaction of 2-(3-cyano-5-hydroxy-1,5-dihydro-2H-pyrrol-2-ylidene)malononitriles with an excess of sodium borohydride resulted in diastereoselective formation of 2,3-diaryl-substituted 4,6-diamino-2,3-dihydrofuro[2,3-b]pyridine-5-carbonitriles. This process was accompanied by opening of the pyrrole ring in the starting compounds, followed by a double reduction and tandem closure of furan and pyridine rings.

This study presents a three-component reaction between malononitrile dimer, α-diketone and aliphatic amine that leads to the formation of previously undescribed alkylammonium 4-cyano-5-(dicyanomethylene)-2-hydroxy-2,3-dimethyl-2,5-dihydropyrrol-1-ides. This reaction is a novel approach for modification of donor–acceptor chromophores containing the buta-1,3-diene-1,1,3-tricarbonitrile moiety.

Reactions of 3,3-dialkyl-4-oxoalkane-1,1,2,2-tetracarbonitriles with water in the presence of pyruvic acid are accompanied by selective quasi-hydrolysis of cyano groups in intermediate 6-hydroxypiperidine-3,4,4-tricarbonitriles.

A method was developed for the synthesis of 4-halo-3-(phenylamino)-furo[3,4-c]pyridin-1(3H)-ones by the reaction of 4-halo-3-hydroxyfuro[3,4-c]pyridin-1(3H)-ones with aniline at room temperature.

Reaction with phenylhydrazine of 3Н-pyrroles spirobound to a furan ring, N-acylimino-substituted 2-oxa-7-azaspiro[4.4]nona-3,6,8-trienes, occurs with a diasteroselective formation of previously unknown derivatives of 1,2,4-triazole: 5-amino-3-(5-alkyl-1-phenyl-1H-1,2,4-triazol-3-yl)-2-morpholin-4-yl-3H-pyrrole-4-carbonitriles.

The reaction of 4-amino-8-hydroxy-1,6-dioxo-2,7-diazaspiro[4.4]non-3-ene-4-carbonitriles with Lawesson's reagent proceeded as an iminothiolactone-thiolactam rearrangement, leading to the formation of 4-amino-6-thioxo-3,7,9-triazatricyclo[6.2.1.01,5]undec-4-ene-2,10-diones.

3-Aryl-4-oxoalkane-1,1,2,2-tetracarbonitriles were synthesized by the interaction of 2-aryl ketones with tetracyanoethylene. Directed rearrangement of them in acetic acid in the presence of ammonium acetate led to the formation of 2-(3-cyano-5-hydroxy-1,5-dihydro-2Hpyrrol-2-ylidene)malononitriles containing an aryl substituent in conjugation with the acceptor buta-1,3-diene-1,1,3-tricarbonitrile moiety.

In this microreview, we describe methods for the synthesis of 5-hydroxyfuran-2(5H)-one derivatives, which have been published over the last 5 years. The main routes for the preparation of 5-hydroxyfuran-2(5H)-one derivatives include transformations of 2-oxocarboxylic acids, formylation or carboxylation of functionalized aromatic (heterocyclic) compounds, as well as synthetic modifications of furan derivatives.

Reaction of 2,2′-(disulfanediyl)bis(1H-pyrrole-3-carbonitriles) with alkyl halides in ethanol in the presence of sodium tetrahydridoborate afforded 2-(alkylsulfanyl)-1H-pyrrole-3-carbonitriles.

A method of synthesis of 9-alkyl-8-methyl-8-methoxy-1,3,6-trioxo-2,7-diazaspiro[4.4]nonane-4-carbonitriles consisting in the reaction of 3-amino-8-hydroxy-1,6-dioxo-2,7-diazaspiro[4.4]non-3-ene-4-carbonitriles with methanol in the presence of sulfuric acid was developed.

Several novel pyrrolo[3,4- c ]pyridine derivatives were synthesized in good yields via hydrolysis and intramolecular heterocyclization of vicinal substituents in compounds of pyrid-2-one series. Both synthesized pyrrolo[3,4- c ]pyridine-1,3,4-triones and 1-iminopyrrolo[3,4- c ]pyridine-3,4-diones are fluorescent in various solvents with emission maxima in the blue-green region of the spectrum.

2-Aminoprop-1-ene-1,1,3-tricarbonitrile (malononitrile dimer) reacted with 1-arylpropane-1,2-diones in ethanol in the presence of piperidine to give new donor–acceptor chromophores, 2-[4-aryl-3-cyano-5-hydroxy-5-methyl-1H-pyrrole-2(5H)-ylidene]malononitriles.

The rearrangement of 4-oxobutane-1,1,2,2-tetracarbonitriles to give the penta-1,3-diene-1,1,3-tricarbonitrile moiety, accompanied by elongation of the carbon chain via introduction of the cyano group carbon atom to the carbon skeleton, is described. The rearrangement in acetic acid in the presence of ammonium acetate allows the synthesis of 2-(3-cyano-7a-hydroxy-5,6,7,7a-tetrahydro-1H-indol-2(4H)-ylidene)malononitriles, which are structural analogs of practically significant tricyanofuran (TCF) and tricyanopyrrole (TCP) acceptors for donor–acceptor chromophores.

Transformation of 3-amino-8-hydroxy-1,6-dioxo-2,7-diazaspiro[4.4]non-3-en-4-carbonitriles in concentrated hydrohalic acid media leads to the obtaining of two classes of fused heterocycles: 4-halogen-3-hydroxy-1,3-dihydrofuro[3,4-c]pyridin-1-ones and octahydropyrrolo[3,4-c]pyrrole-1,3,4,6-tetraones.

Maleimides containing dithienylethene and azobenzene fragments have been synthesized by reaction of dithienyl-substituted maleic anhydrides with 4-aminoazobenzene in boiling toluene in the presence of triethylamine, and their photosensitivity has been studied.

Convenient procedures have been developed for the synthesis of 2-(1,3-dithiolan-2-ylidene)- malononitriles and 2-cyano-2-(1,3-dithiolan-2-ylidene)acetamides from disodium alk-1-ene-1,1-dithiolates and 1,2-dichloroalkanes, as well as from malononitrile or cyanoacetamide in a one-pot mode.

2-(3-Cyano-5-hydroxy-4,5-dimethyl-1H-pyrrol-2(5H)-ylidene)malononitrile was synthesized by the interaction between malononitrile dimer and diacetyl. It reacts with aldehydes in ethanol in the presence of ammonium acetate at room temperature and results 2-(3-cyano-5-hydroxy-5-methyl-4-vinylene-1H-pyrrol-2(5H)-ylidene)malononitriles in 66–86% yield. The developed method is of interest as a promising approach to a novel group of push–pull chromophores, which are functionalized analogs of widely used chromophores of the tricyanofuran (TCF) series.GRAPHICAL ABSTRACT

5-Oxoalkane-2,2,3,3-tetracarbonitriles have been synthesized by reaction of 4-oxoalkane-1,1,2,2-tetracarbonitriles with methyl iodide in dimethyl sulfoxide.

Transformation of 4-oxoalkane-1,1,2,2-tetracarbonitriles under the action of Lawesson's reagent leads to 2,2′-disulfanediylbis(1H-pyrrole-3-carbonitriles) in good yields. The developed method allowed the synthesis of photochromic 2,2′-disulfanediylbis(4,5-bis(2,5-dimethylthiophen-3-yl)-1H-pyrrole-3-carbonitrile).

Non-catalytic conversion of 4-oxoalkane-1,1,2,2-tetracarbonitriles in the presence of water leads to the formation of a mixture of fluorescent 4-cyano-2-oxo-1,2-dihydropyridine-3-carboxamides and 2-oxo-1,2-dihydropyridine-3,4-dicarbonitriles in equal proportions. This transformation was explained, spectral-luminescence properties were investigated, and fluorescence quantum yield was measured.