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1.
Инвентарный номер: нет.
   


   
    1,3,7-triazapyrene-based ortho-carborane fluorophores: convenient synthesis, theoretical studies, and aggregation-induced emission properties / L. A. Smyshliaeva, M. V. Varaksin, E. I. Fomina [et al.] // Organometallics. - 2021. - Vol. 40, № 16. - P2792-2807
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: A convenient transition-metal-free approach, based on nucleophilic substitution of hydrogen (SNH), for consecutive regioselective C–H functionalization of 1,3,7-triazapyrene scaffolds with carboranyllithium and phenyllithium is reported. The theoretical calculations disclosed highlight key features in the regioselectivity and mechanism of the investigated SNH transformations. The novel 1,3,7-triazapyrene-based ortho-carboranes obtained have large potential in the field of molecular electronics as organic luminophores, which are characterized by the aggregation-induced emission and dual-emission effects.

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2.
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   A 10


   
    A new route towards dithienoquinazoline and benzo[f]thieno[3,2-h]quinazoline systems using Pd-catalyzed intramolecular cyclization under microwave irradiation [Electronic resource] / E. V. Verbitskiy, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin // ARKIVOC. - 2016. - № 4. - С. 204-216
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
PYRIMIDINES -- INTRAMOLECULAR CYCLIZATIONS -- FUSED RING SYSTEMS -- THIENOACENES
Аннотация: A novel synthetic route to novel thienoacene systems bearing a fused pyrimidine ring is proposed. The commercially available 5-bromopyrimidine is used as the starting material to obtain various dithienoquinazoline and benzo[f]thieno[3,2-h] quinazoline systems through the Suzuki cross-coupling, nucleophilic aromatic substitution of hydrogen (the S-N(H) reaction), and finally palladium-catalyzed intramolecular cyclization under microwave irradiation. Redox properties of some of the new compounds have been investigated. The data obtained show that these systems have plausible potential for use in organic electronic applications.

\\\\expert2\\NBO\\ARKIVOC\\2016, p.204-216.pdf
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3.
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    Abnormal push-pull benzo[4,5]imidazo[1,2-a][1,2,3]triazolo[4,5-e]pyrimidine fluorophores in planarized intramolecular charge transfer (PLICT) state: Synthesis, photophysical studies and theoretical calculations / O. S. Taniya, V. V. Fedotov, L. K. Sadieva [et al.] // Dyes and Pigments. - 2022. - Vol. 204. - Ст. 110405
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: The combination of excellent luminescence with high solvent polarity effect and aggregation induced emission (AIE) is an ideal combination for creating fluorophores/probes with high microenvironmental sensitivity. However, many push-pull chromophores of the D−A type in common intramolecular charge transfer (ICT) state with a significant solvatochromic effect and AIE activity, have poor luminescent properties. Herein, to overcome this problem by using reactions of nucleophilic aromatic hydrogen substitution (SNH), we have designed a series of novel 4-heteroaryl-substituted 2-aryl-2H-benzo[4,5]imidazo[1,2-a][1,2,3]triazolo[4,5-e]pyrimidine fluorophores possessing a planarized intramolecular charge transfer (PLICT) state. All these fluorophores exhibited high luminescence quantum yields (up to 60%) and large Stokes shift values of up to 7459 cm−1. Among them, the fluorophore 4h was found to exhibit the most pronounced positive solvatochromic effect and the probe 4f exhibited the most pronounced aggregation induced emission characteristics. This AIE behavior was further confirmed by means of time-resolved fluorescence lifetime measurements as well as DFT-assisted geometry optimization studies. In the presence of trifluoroacetic acid (TFA) compound 4h exhibited a well-pronounced acidochromism via visible color change from yellow-green to orange which returned to the original yellow-green solution after the addition of triethylamine (TEA). The Stern-Volmer constant for the probe 4h towards TFA was 38 M−1. Finally, for the compounds 4f, g, h theoretical calculations in the ground and excited states in different solvents were carried out to confirm the PLICT process. Based on all above the herein reported PLICT fluorophores 4a-h can be successfully applied as biological probes and optical switches.

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4.
Инвентарный номер: нет.
   
   A 23


   
    Aerobic oxidative C-H/C-H coupling of azaaromatics with indoles and pyrroles in the presence of TiO2 as a photocatalyst [Electronic resource] / I. A. Utepova, M. A. Trestsova, O. N. Chupakhin, V. N. Charushin, A. A. Rempel // Green Chemistry. - 2015. - Vol. 17, № 8. - С. 4401-4410. - Bibliogr. : p. 4409-4410 (30 ref.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
BOND ACTIVATION -- INHIBITORS -- HYDROGEN
Аннотация: In this paper we wish to report a highly selective and benign method for the double C-H/C-H coupling of azaaromatics with indoles or pyrrole in the presence of air oxygen/TiO2, as an effective photocatalytic oxidative system. It has been shown that this versatile approach can be applied for direct C-H functionalisation of a variety of azaaromatic systems, such as mono-, di- and triazines, substituted and unsubstituted azines and their benzo-annelated analogues.

\\\\expert2\\nbo\\Green Chemistry\\2015, v.17, N 8, p.4401-4410.pdf
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5.
Инвентарный номер: нет.
   
   A 67


   
    Application of 1H and 13C NMR to the structural elucidation of tetrahydroquinoxalines condensed with five-membered heterocycles [Electronic resource] / V. N. Charushin, A. I. Chernyshev, N. N. Sorokin, O. N. Chupakhin // Organic Magnetic Resonance. - 1984. - Vol. 22, № 12. - P775-778. - Bibliogr. : p. 778 (22 ref.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
N-METHYLTETRAHYDROQUINOXALINES -- PYRROLE -- IMIDAZOLE
Аннотация: 1H and 13C NMR spectral data for 21 N-methyltetrahydroquinoxalines annelated with furan, pyrrole, imidazole or thiazole rings are reported. Unambiguous assignments of the ring junction 13C resonances were made on the basis of selective decoupling experiments and with the aid of one-bond and long-range 13C–1H coupling constants. The effects of five-membered heterocycles on the 1H and 13C chemical shifts of the ring junction hydrogen and carbon atoms are considered. Values of one-bond 1J(CH) and vicinal 3J(HH) coupling constants between the ring junction protons are also discussed as a diagnostic means for structural elucidation of tetrahydroquinoxalines condensed with five-membered heterocycles.

\\\\expert2\\nbo\\Organic Magnetic Resonance\\1984. V. 22, N 12. P. 775.pdf
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6.
Инвентарный номер: нет.
   
   B 62


   
    Bis(1,1,1,3,5,5,5-heptafluoro-4-iminopent-2-ene-2-aminato)copper(ii) — a new metal-containing matrix in the design of heterospin systems [Electronic resource] / S. V. Fokin, V. Ovcharenko, G. V. Romanenko, E. V. Tretyakov, A. S. Bogomyakov, V. I. Saloutin, T. I. Filyakova, L. V. Saloutina, V. N. Charushin, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2011. - Vol.60, №5. - С. 816-823. - Bibliogr. : p. 823 (11 ref.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
COPPER(II) -- BISCHELATES -- NITROXIDES
Аннотация: The first heterospin compounds based on bis(1,1,1,3,5,5,5 heptafluoro 4 iminopent 2 ene 2 aminato)copper(II) (CuL2) and nitronyl nitroxide radicals, 2 R 4,4,5,5 tetramethyl 4,5 dihydro 1H imidazole 3 oxide 1 oxyls (NIT R, where R = H, Me, Ph, and 1 methyl pyrazol 4 yl), were synthesized and structurally characterized. An important peculiarity of the structure of synthesized solid phases is the formation of a supramolecular structure due to hydrogen bonds between the oxygen atoms of the nitronyl nitroxide fragments of NIT R and the hydrogen atoms of the NH groups of CuL2

\\\\expert2\\NBO\\Russian Chemical Bulletin\\2011, 60 (5), 816-823.pdf
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7.
Инвентарный номер: нет.
   
   B 68


   
    Blue-light-promoted radical c-h azolation of cyclic nitrones enabled by selectfluor® / A. A. Akulov, M. V. Varaksin, A. N. Tsmokalyuk [et al.] // Green Chemistry. - 2021. - Vol. 23, № 5. - P2049-2057
ББК Г
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: An original approach to achieve the C(sp2)–H azolation of cyclic aldonitrones mediated by Selectfluor® has first been employed. By exploiting a metal-free, visible-light-promoted cross-dehydrogenative C–N coupling reaction between model aldonitrones, 2H-imidazole 1-oxides, and NH-containing azoles, a series of novel azaheterocyclic derivatives have been obtained in yields up to 94%. The elaborated protocol has proved to be appropriate for gram-scale processes and displayed potential for utilization in the synthesis of novel structural analogues of lanabecestat. Besides, mechanistic studies have revealed that this coupling reaction is likely to proceed via a nitroxide-involving radical pathway, encompassing a chain of electron transfer events, such as hydrogen atom transfer (HAT) and single electron transfer (SET).

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8.
Инвентарный номер: нет.
   
   C 10


   
    C-H functionalization of triazolo[a]-annulated 8-azapurines [Electronic resource] / E. B. Gorbunov, G. L. Rusinov, E. N. Ulomskii, V. L. Rusinov, V. N. Charushin, O. N. Chupakhin // Tetrahedron Letters. - 2016. - Vol. 57, № 21. - С. 2303-2305
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
FUSED PYRIMIDINES -- C-H FUNCTIONALIZATION -- 8-AZAPURINES
Аннотация: Direct C-H functionalization of triazolo[a]-annulated 8-azapurines with phenol ethers or thiophene has been performed using the oxidative nucleophilic displacement of a hydrogen on the pyrimidine ring, proceeding through the intermediacy of the corresponding sigma(H)-adducts.

\\\\expert2\\NBO\\Tetrahedron Letters\\2016, v. 57, p. 2303.pdf
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9.
Инвентарный номер: нет.
   
   C 45


   
    Changes in the vibrational characteristics of substituted 1,2,4,5-tetrazines after complexation with 1,2,3-benzotriazole: A theoretical study [Electronic resource] / N. N. Ivshina, E. V. Bartashevich, V. A. Potemkin, M. A. Grishina, R. I. Ishmetova, G. L. Rusinov, N. I. Latosh, P. A. Slepukhin, V. N. Charushin // Journal of Structural Chemistry. - 2009. - Vol. 50, № 6. - P1053-1058
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: The complexation of 3,6-substituted 1,2,4,5-tetrazines with benzotriazole was studied theoretically based on the vibrational spectra. For model complexes, the energy was minimized by the geometrical parameters, and the spectral characteristics were calculated by the PM3 method. The shift of the bond vibration frequencies of the atoms involved in complexation after the formation of different various intermolecular contacts was determined. This made it possible to determine the type of intermolecular interaction and suggest the structures of the complexes

\\\\Expert2\\nbo\\Journal of Structural Chemistry\\2009, V. 50, N 6, p.1053.pdf
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10.
Инвентарный номер: нет.
   


    Charushin, V. N.
    Chemical elements in medicine / V. N. Charushin, Y. A. Titova, E. R. Milaeva // Herald of the Russian academy of sciences. - 2020. - Vol. 90, № 2. - P229-238
Кл.слова (ненормированные):
BETA-LACTAM ANTIBIOTICS -- BORON NEUTRON CAPTURE THERAPY -- FLUOROQUINOLONES -- HETEROCYCLES
Аннотация: A brief review of chemical elements, compounds from which find application in medicine, ranging from the commonly occurring organogenic elements (carbon, hydrogen, nitrogen, oxygen, sulfur, and phosphorus), composing the structure of proteins and nucleic acids of the cells of living organisms and determining the genetic transmission, to native rarely encountered organic fluorine compounds, synthetic derivatives of which have become firmly ingrained in the arsenal of modern pharmaceutical drugs, is given. Strong emphasis is put on metalloproteins, which play a significant role in the biochemistry of vitally essential processes, as well as metal compounds that are widely used in medicine. Of particular importance are the chemical elements and the isotopes, compounds of which are employed in nuclear medicine for diagnostics and treatment of a wide range of diseases, oncological and cardiovascular in particular.

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11.
Инвентарный номер: нет.
   
   C 73


   
    Combination of the Suzuki–Miyaura cross-coupling and nucleophilic aromatic substitution of hydrogen (HSN) reactions as a versatile route to pyrimidines bearing thiophene fragments / E. V. Verbitskiy, E. M. Cherprakova, P. A. Slepukhin, M. I. Kodess, M. A. Ezhikova, M. G. Pervova, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin // Tetrahedron. - 2012. - Vol.68, №27-28. - С. 5445-5452
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
SUZUKI–MIYAURA -- CROSS-COUPLING -- PYRIMIDINES
Аннотация: It has been shown that combination of the Suzuki–Miyaura cross-coupling and nucleophilic aromatic substitution of hydrogen is a versatile method for the synthesis of 4-(thiophen-2-yl)-, 5-(thiophen-2-yl)-, and 4,5-di(thiophen-2-yl) substituted pyrimidines from the commercially available 5-bromopyrimidine. The HSN (AE)- and HSN (AO)-reactions of 5-bromopyrimidine with thiophene and 2-bromothiophene have been studied by gas–liquid chromatography/mass-spectrometry. The structures of intermediate σH-adducts, as well as thiophene-(thiophenyl)pyrimidine and bithiophene-(thiophenyl)pyrimidine dyads have first been established by X-ray crystallography analysis

\\\\Expert2\\nbo\\Tetrahedron\\2012, v. 68, p. 5445.pdf
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12.
Инвентарный номер: нет.
   
   C 75


   
    Consecutive S-N(H) and Suzuki–Miyaura Cross-Coupling Reactions – an Efficient Synthetic Strategy to Pyrimidines Bearing Pyrrole and Indole Fragments / E. V. Verbitskiy, G. L. Rusinov, V. N. Charushin, O. N. Chupakhin, E. M. Cheprakova, P. A. Slepukhin, M. G. Pervova, M. I. Kodess // European Journal of Organic Chemistry. - 2012. - Vol. 2012, №33. - С. 6612-6621
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
SYNTHETIC METHODS -- CROSS-COU­PLING -- NITROGEN HETEROCYCLES
Аннотация: The combination of the Suzuki–Miyaura cross-coupling and nucleophilic aromatic substitution of hydrogen reactions is a versatile tool for the syntheses of 4-(1R-pyrrol-2-yl)- and 4-(1R-indol-3-yl)-5-(hetero)aryl-substituted pyrimidines from commercially available 5-bromopyrimidine. The SNH [AE, (addition–elimination)] and SNH [AO, (addition–oxidation)] reactions of 5-bromopyrimidine with pyrroles and indoles were studied by gas chromatography–mass spectrometry. The structures of the intermediate σH adducts as well as the pyrrole-(hetero)arylpyrimidine and indole-(hetero)arylpyrimidine dyads were established for the first time by X-ray crystal structure analysis

\\\\Expert2\\nbo\\European Journal of Organic Chemistry\\2012, p.6612.pdf
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13.
Инвентарный номер: нет.
   
   P 49


    Pestov, A. V.
    Copper and nickel chelate complexes with polydentate N,O-ligands: structure and magnetic properties of polynuclear complexes [Electronic resource] / A. V. Pestov, P. A. Slepukhin, V. N. Charushin // Russian Chemical Reviews. - 2015. - Vol. 84, № 3. - С. 310-333. - Bibliogr. : p. 331-333(182 ref.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
HYDROGEN-BONDED BRIDGES -- RAY CRYSTAL-STRUCTURE -- SCHIFF-BASE LIGAND
Аннотация: A comparative analysis of the structures of copper(II) and nickel(II) chelate complexes with N-substituted 2-aminoethanols, 3-aminopropan- 1 -ols, glycines and beta-alanines is performed. It is shown that tetradentate ligands based on 3-aminopropan- 1 -ol and P-alanine, sterically hindered 2-aminoethanol derivatives and tridentate enamino ketone derivatives tend to form oligonuclear copper(II) and nickel(II) complexes. Glycine derivatives do not provide the formation of oligonuclear copper(II) and nickel(II) complexes. The magnetic properties of a number of polynuclear complexes are compared.

\\\\expert2\\nbo\\Russian Chemical Reviews\\2015, V.84, N38, p. 310-333.pdf
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14.
Инвентарный номер: нет.
   
   D 46


   
    Design and antioxidant properties of bifunctional 2H-imidazole-derived phenolic compounds-a new family of effective inhibitors for oxidative stress-associated destructive processes / E. L. Gerasimova, E. R. Gazizullina, M. V. Borisova [et al.] // Molecules. - 2021. - Vol. 26, № 21. - Ст. 6534
ББК Г
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
2H-IMIDAZOLE -- POLYPHENOLS -- ANTIOXIDANT CAPACITY -- ANTIRADICAL CAPACITY
Аннотация: The synthesis of inhibitors for oxidative stress-associated destructive processes based on 2H-imidazole-derived phenolic compounds affording the bifunctional 2H-imidazole-derived phenolic compounds in good-to-excellent yields was reported. In particular, a series of bifunctional organic molecules of the 5-aryl-2H-imidazole family of various architectures bearing both electron-donating and electron-withdrawing substituents in the aryl fragment along with the different arrangements of the hydroxy groups in the polyphenol moiety, namely derivatives of phloroglucinol, pyrogallol, hydroxyquinol, including previously unknown water-soluble molecules, were studied. The structural and antioxidant properties of these bifunctional 5-aryl-2H-imidazoles were comprehensively studied. The redox transformations of the synthesized compounds were carried out. The integrated approach based on single and mixed mechanisms of antioxidant action, namely the AOC, ARC, Folin, and DPPH assays, were applied to estimate antioxidant activities. The relationship “structure-antioxidant properties” was established for each of the antioxidant action mechanisms. The conjugation effect was shown to result in a decrease in the mobility of the hydrogen atom, thus complicating the process of electron transfer in nearly all cases. On the contrary, the conjugation in imidazolyl substituted phloroglucinols was found to enhance their activity through the hydrogen transfer mechanism. Imidazole-derived polyphenolic compounds bearing the most electron-withdrawing functionality, namely the nitro group, were established to possess the higher values for both antioxidant and antiradical capacities. It was demonstrated that in the case of phloroglucinol derivatives, the conjugation effect resulted in a significant increase in the antiradical capacity (ARC) for a whole family of the considered 2H-imidazole-derived phenolic compounds in comparison with the corresponding unsubstituted phenols. Particularly, conjugation of the polyphenolic subunit with 2,2-dimethyl-5-(4-nitrophenyl)-2H-imidazol-4-yl fragment was shown to increase ARC from 2.26 to 5.16 (104 mol-eq/L). This means that the considered family of compounds is capable of exhibiting an antioxidant activity via transferring a hydrogen atom, exceeding the activity of known natural polyphenolic compounds.

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15.
Инвентарный номер: нет.
   
   D 62


   
    Direct arylalkenylation of furazano[3,4-b]pyrazines via a new C-H functionalization protocol [Electronic resource] / N. A. Kazin, Yu. A. Kvashnin, R. A. Irgashev, W. Dehaen, G. L. Rusinov, V. N. Charushin // Tetrahedron Letters. - 2015. - Vol. 56, № 14. - С. 1865-1869. - Bibliogr. : p. 1869 (20 ref.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
NUCLEOPHILIC-SUBSTITUTION -- DERIVATIVES -- HYDROGEN
Аннотация: 6-Styryl-5-(het)arylfurazano[3,4-b]pyrazines have been obtained by novel C-H functionalization, which is a particular case of the nucleophilic substitution of hydrogen (S-N(H)). The process is initiated by the Michael addition of morpholine at the C=C double bond of beta-nitrostyrenes, and the subsequent addition of the generated carbanion to C-6 of 5-(het)arylfurazano[3,4-b]pyrazines, followed by elimination of nitrous acid and morpholine. It has been shown that in this case, only beta-nitrostyrenes bearing electron-rich substituents on the aromatic ring are involved in arylalkenylation of furazano[3,4-b]pyrazines

\\\\expert2\\nbo\\Tetrahedron Letters\\2015, v. 56, p. 1865.pdf
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16.
Инвентарный номер: нет.
   


   
    Direct c-li/c-h coupling of c6f5li with azines and azoles n-oxides as efficient approach toward to polyfloorinated azaheterocycles / T. D. Moseev, M. V. Varaksin, E. A. Virlova [et al.] // Actual problems of organic chemistry and biotechnology. - Екатеринбург, 2020. - P276-277
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
C-C COUPLING -- NUCLEOPHILIC SUBSTITUTION OF HYDROGEN -- FLUORINE -- FLUORARENES

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17.
Инвентарный номер: нет.
   
   D 62


   
    Direct nucleophilic functionalization of C(sp2)–H-bonds in arenes and hetarenes by electrochemical methods [Electronic resource] / A. V. Shchepochkin, O. N. Chupakhin, V. N. Charushin, V. A. Petrosyan // Russian Chemical Reviews. - 2013. - Vol.82, №8. - С. 747-772. - Bibliogr. : p. 770-772 (133 ref.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
NUCLEOPHILIC FUNCTIONALIZATION -- C(sp2)–H-BONDS -- HETARENES
Аннотация: The data on the main electrochemical methods and approaches used for the direct functionalization of the C(sp2)–H-bond proceeding via the mechanisms of nucleophilic substitution of hydrogen (SNH-reaction) are classified and summarized. The important features of preparative electrochemical processes are considered. A special emphasis is placed on the synthetic potential of the discussed transformations

\\\\expert2\\NBO\\Russian Chemical Reviews\\2013, V.82, N8, p.747.pdf
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18.
Инвентарный номер: нет.
   
   F 70


   
    Fluoro-containing Heterocycles: VI. New Derivatives of 1,3,4-Thiadiazino[6,5,4-i,j]quinoline [Electronic resource] / E. V. Nosova, G. N. Lipunova, L. P. Sidorova, V. N. Charushin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2001. - Vol. 37, № 8. - P1169-1176
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: A series of new tricyclic fluoroquinolones was prepared by replacing fluorine atoms in derivatives of 2-R-8-Y-7-oxo-9,10-difluoro-7H-1,3,4-thiadiazino[6,5,4-i,j]quinoline-6-carboxylic acids. In acids and esters containing a hydrogen atom in position 8 occurred replacement of F10 by amine rests, and in compounds with a fluorine in position 8 was substituted either F8or F10 and F8depending on the amine character

\\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2001, 37 (8), 1169.pdf
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19.
Инвентарный номер: нет.
   
   H 62


   
    Heteroacenes Bearing the Pyrimidine Scaffold: Synthesis, Photophysical and Electrochemical Properties [Electronic resource] / E. V. Verbitskiy [и др.] // European Journal of Organic Chemistry. - 2016. - Vol. 2016, № 7. - С. 1420-1428
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
PYRIMIDINE SCAFFOLD -- PERIMIDINE SYSTEMS -- BORONIC ACIDS
Аннотация: A convenient synthetic route to novel 7-​substituted benzo[f]​thieno[3,​2-​h]​quinazoline and 8-​substituted benzo[g,​h]​dithieno[2,​3-​e:3',​2'-​j]​perimidine systems, bearing the fused pyrimidine ring, has been advanced. A com. available 5-​bromopyrimidine was used as the starting material to obtain various polycyclic systems through the sequence of nucleophilic arom. substitution of hydrogen (the SNH reaction)​, Suzuki cross-​coupling and oxidative photocyclization. Evidence for the structure of benzo[g,​h]​dithieno[2,​3-​e:3',​2'-​j]​perimidines has been obtained by X-​ray crystallog. anal. MO calcns. (DFT)​, as well as redox and optical measurements for all new compds. have been performed. The data show that the reported polycyclic systems have potential for use in org. electronic applications. The synthesis of the target compds. was achieved using 5-​bromo-​4-​(2-​thienyl)​pyrimidine and (phenyl)​boronic acids as starting materials.

\\\\expert2\\NBO\\European Journal of Organic Chemistry\\2016, № 7, p. 1420-1428.pdf
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20.
Инвентарный номер: нет.
   
   I-69


   
    Intramolecular nucleophilic substitution of hydrogen in (quinoxalinyl-2)aminovinyl derivatives as a new approach to pyrrolo- and indolo[2,3-beta]quinoxalines [Text] / S. K. Kotovskaya, V. N. Charushin, N. M. Perova, M. I. Kodess, O. N. Chupakhin // Synthetic Communications. - 2004. - Vol. 34, № 14. - P2531-2537 : ил. - Библиогр.: с. 2537 (10 ref.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
NUCLEOPHILIC SUBSTITUTION -- HYDROGEN -- KETONE
Аннотация: Pyrrolo[2,3-beta]- and indolo[2,3-e]quinoxalines were obtained by the reaction of 2-aminoquinoxalines with ketones followed by the intramolecular displacement of hydrogen at C-3 in (quinoxalinyl-2)aminovinyl derivatives.

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