R 30 Reaction of 2-amino-4-imino-2-perfluoropentene with ethylenediamine and diethylenetriamine [Electronic resource] / V. I. Saloutin, Z. E. Skryabina, Ya. V. Burgart, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 1993. - Vol. 42, № 10. - P1697-1700 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The transamination of 2-amino-4-imino-2-perfluoropentene with ethylenediamine gives the corresponding 6-fluoro-5,7-bis(trifluoromethyl)-2,3-dihydro-1H-1,4-diazepine. The transamination of 2-amino-4-imino-2-perfluoropentene by diethylenetriamine is accompanied by intramolecular nucleophilic substitution of the ?-fluorine atom to form 1,9-bis(trifluoromethyl)-3,4,6,7-tetrahydro-2H-pyrazino[1,2-a]pyrazine whose structure was established by an X-ray structural investigation. Several salts of this bicyclic compound and its complex with BF3 have been described \\\\Expert2\\nbo\\Russian Chemical Bulletin\\1993, 42 (10), 1697.pdf |
M 81 Mono- and diadducts and bicyclic adducts in reactions of 2,3-dicyano-1-ethylpyrazinium cation with C- and O-nucleophiles [Electronic resource] / P. A. Slepukhin, G. L. Rusinov, V. N. Charushin, V. I. Filyakova, N. S. Karpenko, D. B. Krivolapov, I. A. Litvinov // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2004. - Vol. 53, № 6. - P1272-1278 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Products of diaddition of O- and C-nucleophiles to the 2,3-dicyano-1-ethylpyrazinium cation were isolated for the first time. The tandem AN—AN reactions of 2,3-dicyano-1-ethylpyrazinium tetrafluoroborate with 1,3-diketone enolates or keto esters afforded tetrahydrofuro[2,3-b]pyrazine derivatives, whereas cyclization with ethylene glycol gave tetrahydro-1,4-dioxino[2,3-b]pyrazine. Crystallographic data on the three-dimensional structures of these compounds were reported \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2004, 53 (6), 1272.pdf |
F 98 Fused polycyclic nitrogen-containing heterocycles. 11. 4-Hydroxy-3,5-diphenyl-2-phenyliminothiazolidines as new key compounds in the synthesis of thiazolo[3,4-a]quinoxaline derivatives [Electronic resource] / V. A. Mamedov, I. Z. Nurkhametova, S. K. Kotovskaya, Ya. A. Levin, A. T. Gubaidullin, I. A. Litvinov, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2004. - Vol. 53, № 11. - P2568-2576 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A procedure was developed for the synthesis of thiazolo[3,4-a]quinoxaline derivatives based on a new strategy for construction of the pyrazine ring. The key step of the process involves the reaction of 4-hydroxy-3,5-diphenyl-2-phenyliminothiazolidines with o-phenylenediamines \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2004, 53 (11), 2568.pdf |
I-83 ipso- and tele-Substitution in reactions of 3-chloro-1-ethyl-2-R-pyrazinium salts with C-nucleophiles [Electronic resource] / P. A. Slepukhin, G. L. Rusinov, V. N. Charushin, M. I. Kodess, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2003. - Vol. 52, № 3. - P689-694 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The reactions of 2,3-dichloro- and 3-chloro-1-ethyl-2-morpholinopyrazinium tetrafluoroborates with compounds containing the active methylene group were studied. The reactions with malonodinitrile and cyanoacetic ester afford products of ipso-substitution at position 2, while 1,3-dicarbonyl compounds produce products of tele-substitution of the Cl atom at the C(3) atom due to the attack of a nucleophile to position 6 of the pyrazine cycle \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2003, 52 (3), 689.pdf |
T 82 Transformations of 8-substituted tetrazolo[1,5-a]pyrazines [Electronic resource] / P. A. Slepukhin, G. L. Rusinov, S. Dedeneva, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2007. - Vol. 56, № 2. - P345-350 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The reactions of 8-chlorotetrazolo[1,5-a]pyrazine with N-, O-, and S-nucleophiles involve the ipso substitution of the chlorine atom. Heating of this compound with benzotriazole or phenyltetrazole results in elimination of the nitrogen molecule from one of the tetrazole rings to form new annelated azapentalenes \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2007, 56 (2), 345.pdf |
S 10 S-N(H) reactions of pyrazine N-oxides and 1,2,4-triazine 4-oxides with CH-active compounds [Electronic resource] / D. N. Kozhevnikov, I. S. Kovalev, A. M. Prokhorov, V. L. Rusinov, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2003. - Vol. 52, № 7. - P1588-1594 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Nucleophilic substitution of hydrogen in pyrazine N-oxides under the action of CH-active compounds requires activation with acylating agents. This activation facilitates aromatization of intermediate H adducts via elimination of the acid residue to form substituted pyrazines. More electrophilic 1,2,4-triazine 4-oxides react with carbanions derived from CH-active compounds without additional activation according to a scheme, which has previously been unknown for azine N-oxides. This scheme involves aromatization of H adducts through elimination of water by the E1cb mechanism. The reaction products occur in DMSO-d6 solutions predominantly as 6-methylene-1,6-dihydropyrazines and 5-methylene-4,5-dihydro-1,2,4-triazines.??nucleophilic substitution of hydrogen - 1,2,4-triazine 4-oxide - pyrazine 1-oxide - carbanion - CH-active compounds?? \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2003, 52 (7), 1588.pdf |
S 10 S-N(H) reactions of 1,2,4-triazine N-oxides, pyrazine N-oxides, and pterin N-oxides with arenethiols [Electronic resource] / D. N. Kozhevnikov, I. S. Kovalev, V. L. Rusinov, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2001. - Vol. 50, № 6. - P1068-1071 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: 1,2,4-Triazine 4-oxides were found to enter into the reactions of nucleophilic substitution of hydrogen with S-nucleophiles (arenethiols) in the presence of acylating agents and trifluoroacetic acid. The reactions proceeded with loss of the N-oxide function to form 5-arylthio-1,2,4-triazines. 2-Amino-3-ethoxycarbonylpyrazine 1-oxides and 2-amino-4-oxopterin 8-oxides react with arenethiol analogously \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2001, 50 (6), 1068.pdf |
R 30 Reactions of sigma(H)-adducts of 1-ethyl-1,4-diazinium salts with arylalkynes as a one-step approach to pyrrolo[1,2-a]pyrazine derivatives [Electronic resource] / E. V. Verbitskiy, P. A. Slepukhin, M. A. Ezhikova, M. I. Kodess, G. L. Rusinov, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2009. - Vol. 58, № 6. - P1291-1293 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The O- and C-adducts of 5-aryl and 5-hetaryl-2,3-dicyano-1-ethylpyrazinium salts are hidden sources of ylides, which can be used for the cyclization with arylacetylenes giving rise to pyrrolo[1,2-a]pyrazines \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2009, 58 (6), 1291-1293.pdf |
F 42 Ferro- and antiferromagnetic interactions in polymeric and molecular complexes of Cu(hfac)2 with 1-oxoazin-2-yl-substituted nitronyl nitroxides [Text] / O. N. Chupakhin, E. V. Tretyakov, I. A. Utepova, M. V. Varaksin, G. V. Romanenko, A. S. Bogomyakov, S. L. Veber, V. Ovcharenko // Polyhedron. - 2011. - Vol. 30, № 4. - P647-653. - Bibliogr. : p. 653 (9 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Solid heterospin compounds based on Cu(hfac)2 complexes with a new group of nitronyl nitroxides bearing different azine-N-oxide substituents at position 2 of the 2-imidazoline ring (Ln) were studied. The major factor responsible for the change in the magnetic characteristics of the [Cu(hfac)2L1] complex with triazine nitronyl nitroxide with temperature was shown to be the specific pairwise packing of heterospin molecules with the dominant antiferromagnetic exchange between the radical fragments of adjacent molecules. For complexes of Cu(hfac)2 with 1-oxoazin-2-yl-substituted nitronyl nitroxides L2 and L4, 7-membered metallocycles were obtained, although they form rarely. It was shown that polymer chains formed in the solid complex with spin-labeled pyrazine-N-oxide [(Cu(hfac)2)3(L3)2] due to the cross-linking of {(Cu(hfac)2)2(L3)2} binuclear fragments via the bridging [Cu(hfac)2].???? \\\\Expert2\\nbo\\Polyhedron\\2011. v.30. p.647.pdf |
N 50 Neutral tetranuclear Cu(II) complex of 2,6-di(5-trifluoromethylpyrazol-3-yl)pyridine: Synthesis, characterization and its transformation with selected aza-ligands [Электронный ресурс] / E. F. Zhilina, D. L. Chizhov, A. A. Sidorov, G. G. Aleksandrov, M. Kiskin, P. A. Slepukhin, M. Fedin, V. N. Charushin // Polyhedron. - 2013. - Vol.53. - P122-131 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): COPPER (II) COMPLEX -- X-RAY -- MAGNETIC PROPERTIES Аннотация: New tetranuclear Cu(II) complex [Cu4(L)4]·MeCN (1) with 2,6-di(5-trifluoromethyl-1H-pyrazol-3-yl)pyridine (H2L) was synthesized. It has been shown that treatment of 1 with selected aza-ligands (pyridine, 2,2′- and 4,4′-bipyridyl, 2,3,5,6-tetra-(pyridine-2-yl)pyrazine, 2,2′;6′,2″-terpyridine and 1,4-diazabicyclo[2.2.2]octane) leads to formation of other Cu(II) complexes with different nuclearity: [Cu(L)py2] (2), [Cu(L)(2,2′-bpy)] (3), [Cu(L)2(tppz)]·THF (5), [Cu(L)tpy]·C6H5CN (4), {[Cu2(L)2(4,4′-bpy)2]·(C6H5CH3)·MeCN}n (6) and {[Cu(L)DABCO]·2MeCN}n (7). Obtained compounds were characterized by IR spectroscopy, X-ray crystallography data, EPR and SQUID magnetic measurements. -------------------------------------------------------------------------------- \\\\Expert2\\NBO\\Polyhedron\\2013. v.53. p.122.pdf |
D 47 Detection of nitroaromatic explosives by 2-amino-3-ethoxycarbonyl-6-(1-methylindol-3-yl)-5-(4-chlorophenyl)-pyrazine and its derivatives / O. S. Taniya, L. K. Sadieva, I. S. Kovalev, G. V. Zyryanov, D. S. Kopchuk, V. L. Rusinov, O. N. Chupakhin // Современные синтетические методологии для создания лекарственных препаратов и функциональных материалов (MOSM2018): вторая международная научно-практическая конференция : материалы и доклады. - Екатеринбург, 2019. - С. 211 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
Synthesis and characterization of linear 1,4-diazine-triphenylamine–based selective chemosensors for recognition of nitroaromatic compounds and aliphatic amines / E. V. Verbitskiy, Y. A. Kvashnin, E. F. Zhilina [et al.] // Dyes and pigments. - 2020. - Vol. 178. - P108344 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): ALIPHATIC AMINES -- FLUORESCENCE QUENCHING -- NITROAROMATIC COMPOUNDS -- PYRAZINE -- QUINOXALINE -- SOLVATOCHROMISM Аннотация: Novel 1,4-diazine-based dyes of the D–π–A type, possessing triphenylamine as an electron-donating group, have been developed. Fluorescence studies have demonstrated that emission of these fluorophores is sensitive towards different nitroaromatic compounds and aliphatic amines, both in solutions and in a vapor phase. Moreover, these compounds can be considered as “naked-eye” fluorescent probes for solution polarity because they possess pronounced solvatochromic properties. Therefore, these compounds have to be regarded as potential multifunctional chemosensors for monitoring hazardous organic substances. |
Design of fluorescent sensors based on azaheterocyclic push-pull systems towards nitroaromatic explosives and related compounds: a review / E. V. Verbitskiy, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin // Dyes and pigments. - 2020. - Vol. 180. - P108414 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): NITROAROMATIC EXPLOSIVES -- FLUORESCENCE QUENCHING -- PYRIDINES -- PYRAZINE -- PYRIMIDINES -- TRIAZINES Аннотация: Highly sensitive and selective detection of nitro containing high energy organic compounds such as picric acid (PA), 2,4,6-trinitrotoluene (TNT) and 2,4-dinitrotoluene (DNT) has become a challenging task due to concerns over national security, criminal investigations and environment protections. Among various known detection methods, fluorescence sensors have gained special attention in recent time. The family of fluorescent sensors based on push-pull systems that incorporate nitrogen heterocycles as an electron-withdrawing group have a growing interest due to their high sensitivity, selectivity and easy tuning. The fluorescent sensors discussed in this review are classified and organized according to used azaheterocyclic scaffold, their functionality and their ability to detect of nitroaromatics by fluorescence quenching. |
Azaheterocyclic push-pull chromophores: synthesis, photophysical properties and applications as fluorescent sensors / E. V. Verbitskiy, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin // Actual problems of organic chemistry and biotechnology. - Екатеринбург, 2020. - P73-75 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): PYRIMIDINE -- PYRAZINE -- FLUORESCENCE QUENCHING -- PUSH-PULL FLUOROPHORES |
Synthesis, crystal structures and properties of carbazolebased [6]helicenes fused with an azine ring / D. I. Tonkoglazova, A. V. Gulevskaya, O. I. Askalepova, K. A. Chistyakov // Beilstein journal of organic chemistry. - 2021. - Vol. 17. - P11-21 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): AZINE-FUSED HELICENES -- CARBAZOLE-BASED [6]HELICENES -- HELICAL STRUCTURES Аннотация: Novel carbazole-based [6]helicenes fused with an azine ring (pyridine, pyrazine or quinoxaline) have been prepared through a five-step synthetic sequence in good overall yields. Commercially available 2,3-dihaloazines were used as starting materials. To discern the effect of merging an azine moiety within a helical skeleton, the X-ray structures, UV–vis absorption and fluorescence spectra of the helicenes were investigated and compared to that of the parent carbazole-based [6]helicene (7H-phenanthro[3,4-c]carbazole). |
Push–pull derivatives based on 2,4'-biphenylene linker with quinoxaline, [1,2,5]oxadiazolo[3,4-b]pyrazine and [1,2,5]thiadiazolo[3,4-b]pyrazine electron withdrawing parts / E. V. Verbitskiy, Y. A. Kvashnin, G. L. Rusinov [et al.] // Molecules. - 2022. - Vol. 27, № 13. - Ст. 4250 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A series of novel V-shaped quinoxaline, [1,2,5]oxadiazolo[3,4-b]pyrazine and [1,2,5]thiadiazolo[3,4-b]pyrazine push–pull derivatives with 2,4′-biphenylene linker were designed and their electrochemical, photophysical and nonlinear optical properties were investigated. [1,2,5]Oxadiazolo[3,4-b]pyrazine is the stronger electron-withdrawing fragment as shown by electrochemical, and photophysical data. All compounds are emissive in a solid-state (from the cyan to red region of the spectrum) and quinoxaline derivatives are emissions in DCM solution. It has been found that quinoxaline derivatives demonstrate important solvatochromism and extra-large Stokes shifts, characteristic of twisted intramolecular charge transfer excited state as well as aggregation induced emission. The experimental conclusions have been justified by theoretical (TD-)DFT calculations. |
Modification and application of 1,2,5-oxadiazolo[3,4-b]pyrazine derivatives: highlights and perspectives / Yu. A. Kvashnin, E. V. Verbitskiy, G. L. Rusinov, V. N. Charushin // Russian chemical bulletin. - 2022. - Vol. 71, № 7. - P1342-1362 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
Synthesis and properties of azines functionalized graphene with extremely high adsorptive ability to Eu3+ ions / O. N. Chupakhin, A. A Musikhina, I. A. Utepova [et al.] // Flatchem. - 2022. - Vol. 33. - P100348 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: In this work, a versatile synthetic protocol for obtaining of new promising carbon materials based on the C–C coupling of graphenide lithium species with azaaromatic compounds (1,10-phenanthroline, phenyl-1,2,5-oxadiazolo[3,4-b]pyrazine) has been suggested. It was shown that more electrophilic oxadiazolopyrazine gave the product with high degree of graphene functionalization and demonstrated non-isomorphic properties. At the same time, phenanthrolinyl graphene has less functionalization degree due to a lower electrophilicity of azine. However, the large size of pores between organic residues in phenanthrolinyl graphene allows adsorbing almost 10% of Eu3+. The mesurment of adsorption isotherm showed an extremely high affinity of phenanthrolinylgraphene to Eu (III) ions in netural or alkaline conditions, and the obtained hybrid material could work at least 5 sorption/desorption cycles. The structures of azine-graphene dyads were verified by complex of modern physicochemical analyses methods (the Raman spectroscopy, FTIR, XPS, SEM, EDS and TGA analyses). |