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1.
Инвентарный номер: нет.
   


   
    15N chemical shifts and Jnn-couplings as diagnostic tools for determination of the azide-tetrazole equilibrium in tetrazoloazines / S. L. Deev, T. S. Shestakova, Z. O. Shenkarev [et al.] // Journal of Organic Chemistry. - 2022. - Vol. 87, № 1. - P211–222
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: Selectively 15N-labeled tetrazolo[1,5-b][1,2,4]triazines and tetrazolo[1,5-a]pyrimidines bearing one, two, or three 15N labels were synthesized. The synthesized compounds were studied by 1H, 13C, and 15N NMR spectroscopy in DMSO and TFA solutions, where the azide–tetrazole equilibrium can lead to the formation of two tetrazole (T, T′) isomers and one azide (A) isomer for each compound. Incorporation of the 15N-label(s) leads to the appearance of 15N–15N coupling constants (JNN), which can be easily measured via simple 1D 15N NMR spectra, even at natural abundance between labeled and unlabeled 15N atoms. The chemical shifts for the 15N nuclei in the azole moiety are very sensitive to the ring opening and azide formation, thus providing information about the azido–tetrazole equilibrium. At the same time, the 1–2JNN couplings between 15N-labeled atoms in the azole and azine fragments unambiguously determine the fusion type between tetrazole and azine rings in the cyclic isomers T and T′. Thus, combined analysis of 15N chemical shifts and JNN values in selectively isotope-enriched compounds provides an effective diagnostic tool for direct structural determination of tetrazole isomers and azide form in solution. This method was found to be the most simple and efficient way to study the azido–tetrazole equilibrium.

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2.
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    1H and 13C NMR spectra of tetrahydroquinoxalines condensed with six-membered heterocycles [Electronic resource] / V. N. Charushin, N. N. Sorokin, A. I. Chernyshev, V. G. Baklykov, M. G. Ponizovskii, O. N. Chupakhin // Magnetic Resonance in Chemistry. - 1986. - Vol. 24, № 9. - С. 777-782. - Bibliogr. : p. 782 (16 ref.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
1H NMR -- 13C NMR -- CONDENSED TETRAHYDROQUINOXALINES
Аннотация: The 1H and 13C NMR spectra of tetrahydroquinoxalines condensed with pyridazine, pyrazine, oxazine, oxadiazine, thiadiazine or triazine rings have been measured in DMSO-d6 solution. The effects of six-membered heterocycles on 1H and 13C chemical shifts and the values of one-bond 1J(CH) and vicinal 3J(HH) coupling constants for the ring junction fragment are considered. The differences between the 1H and 13C spectral parameters of tetrahydroquinoxalines annelated with five- or six-membered heterocycles with the same set of heteroatoms attached to the ring junction carbons are also discussed.

\\\\expert2\\nbo\\Magnetic Resonance in Chemistry\\1986, v.24, N 9, p.777.pdf
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3.
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    2-Aminooxazoles as novel dienophiles in the inverse demand Diels–Alder reaction with 1,2,4-triazines / A. P. Krinochkin, G. Mallikarjuna Reddy, D. S. Kopchuk [et al.] // Mendeleev Communications. - 2021. - Vol. 31, № 4. - P542-544
ББК Г
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
1,2,4-TRIAZINES -- OXAZOL-2-AMINES -- DIELS–ALDER REACTION -- 2,2'-BIPYRIDIN-3-OLS
Аннотация: High temperature coupling of 6-aryl-5-cyano-3-(pyridin-2-yl)-1,2,4-triazines with 2-amino-4-aryloxazoles proceeds as the inverse demand Diels–Alder reaction between the oxazole moiety as dienophile and the 1,2,4-triazine moiety as diene to construct new 4,5-diaryl-6-cyano-3-hydroxypyridin-2-yl fragment. A reaction mechanism is proposed, and the structure of the key-product is proved by the X-ray diffraction analysis.

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4.
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    A BF3-mediated C–H/C–Li coupling of 1,3,7-triazapyrene with 2-thienyllithium in the design of push–pull fluorophores and chemosensors for nitroaromatics / I. A. Lavrinchenko, T. D. Moseev, M. V. Varaksin [et al.] // New Journal of Chemistry. - 2022. - Vol. 46, № 11. - P5121-5128
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: Mono- and bis-2-thienyl-substituted 1,3,7-triazapyrenes have been synthesized for the first time via BF3-mediated C–H/C–Li coupling of 1,3,7-triazapyrene with 2-thienyllithium in 33 and 51% yields, respectively. The photophysical properties of these polycyclic azaaromatics have been studied, with emission in the range of 450–500 nm and fluorescence quantum yields of up to 99% in methanol solutions being revealed. The turn-off chemosensing properties of 2-thienyl-substituted 1,3,7-triazapyrenes for the selective detection of nitroaromatics have also been assessed; in particular, the quenching constants according to the Stern–Volmer model, the quenching sphere radius according to the Perrin model, the detection limit and the quenching efficiency have been determined. In particular, 6,8-bis-(thiopen-2-yl)-1,3,7-triazapyrene, characterized by 10 times the quenching constant and limit of detection (LOD) compared to the mono-substituted analog, can be considered as the most promising chemosensor for determining nitroaromatic compounds. DFT calculations confirm the presence of intramolecular charge transfer (ICT) effects in the case of the obtained fluorophores and clarify the quenching mechanism for nitroaromatics.

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5.
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   A 10


   
    A facile, metal-free, oxidative coupling of new 6-(hetero)aryl-[1,2,5]oxadiazolo[3,4-b]pyrazines with pyrroles, indoles and carbazoles. / Yu. A. Kvashnin, N. A. Kazin, E. V. Verbitskiy, T. S. Svalova, A. V. Ivanova, A. Kozitsina, P. A. Slepukhin, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin // ARKIVOC. - 2016. - Vol. V. - С. 279-300. - Bibliogr. : p. 297-300 (45 ref.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
PYRAZINES -- PYRROLES -- INDOLES

\\\\expert2\\NBO\\ARKIVOC\\2016, p.279-300.pdf
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6.
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   A 10


   
    A new approach to 4-arylstyrenes: microwave-assisted synthesis and photophysical properties / M. Z. Eddin, M. G. Pervova, E. F. Zhilina [et al.] // Russian chemical bulletin. - 2021. - Vol. 70, № 11. - P2139-2144
ББК Г
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
STYRENE -- 4-VINYLBIPHENYL DERIVATIVES -- SUZUKi—MIYAURA CROSS-COUPLING -- FLUORESCENCE

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7.
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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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8.
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   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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9.
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   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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10.
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    Assembly of annulated 1,3-diazapyrenes by consecutive cross-coupling and cyclodehydrogenation of (het)arene moieties / E. V. Verbitskiy, E. M. Dinastiya, O. S. Eltsov [et al.] // Mendeleev communications. - 2020. - Vol. 30, № 2. - P142-144
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: Di(het)areno[e,l][1,3]diazapyrene core was constructed by FeCl3-mediated intramolecular oxidative cyclodehydrogenation of 5-[2,6-di(het)arylphenyl]pyrimidine precursors, which in turn were obtained by the Suzuki cross-coupling of 5-(2,6-dibromophenyl)pyrimidine derivative with the corresponding (het)arylboronic acids. Molecular orbital calculations as well as redox and photophysical measurements show that the fused products are promising for organic electronic application.

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