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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.
Инвентарный номер: нет.
   
   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.
Инвентарный номер: нет.
   
   A 53


   
    An unusual aromatisation of dihydropyrimidines facilitated by reduction of the nitro group [Electronic resource] / G. L. Rusinov, E. B. Gorbunov, V. N. Charushin, O. N. Chupakhin // Tetrahedron Letters. - 2007. - Vol. 48, № 33. - P5873-5876
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: An unusual aromatisation of the dihydropyrimidine fragment in 6-nitro-7-substituted-4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidines has first been found to occur in parallel with reduction of the nitro group using a number of reducing agents.

\\\\Expert2\\nbo\\Tetrahedron Letters\\2007, v. 48, p.5873.pdf
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4.
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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5.
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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6.
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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7.
Инвентарный номер: нет.
   
   C 75


   
    Consecutive SNH and Pd-catalyzed coupling reactions – an efficient synthetic strategy to pyrimidines bearing electron-rich heterocyclic fragments / V. N. Charushin, O. N. Chupakhin, G. L. Rusinov, E. V. Verbitskiy, E. M. Cherprakova // 18th European Symposium on Organic Chemistry ESOC-2013, Marseille, France, 7-12 July 2013 : book of abstracts. - 2013. - 158 (P1-089)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
SYNTHESIS -- Pd-CATALYZED -- HETEROCYCLIC FRAGMENTS

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8.
Инвентарный номер: нет.
   


   
    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.

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9.
Инвентарный номер: нет.
   
   D 47


   
    Detection of nitroaromatic explosives by new D-π-A sensing fluorophores on the basis of the pyrimidine scaffold [Electronic resource] / E. V. Verbitskiy, A. A. Baranova, K. I. Ludovik, M. Z. Shafikov, K. O. Khokhlov, E. M. Cheprakova, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin // Analytical and Bioanalytical Chemistry. - 2016. - Ahead of Print
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
NITROAROMATIC EXPLOSIVES -- PYRIMIDINE SCAFFOLD
Аннотация: A series of D-​π-​A- type dyes based on pyrimidines, bearing various thiophene linkers, have been studied as sensing fluorophores. Fluorescence studies have demonstrated that the emission of all derivs. is sensitive to the presence of nitroarom. explosives, such as 2,​4,​6-​trinitrophenol (PA)​, 2,​4,​6-​trinitrotoluene (TNT)​, and 2,​4-​dinitrotoluene (DNT)​, in their acetonitrile solns. The detection limits of fluorophores to PA, TNT, and DNT proved to be in the range from 5.83 × 10-​6 to 2.38 × 10-​7 mol​/L, 1.70 × 10-​4 to 8.40 × 10-​6 mol​/L, and 8.39 × 10-​5 to 6.87 × 10-​6 mol​/L, resp. The theor. investigation into the quenching mechanism in the presence of fluorophore has been performed. All compds. have shown a good efficiency as sensor materials when tested as elements of the original device <> for detecting nitro-​contg. explosives in vapor phase

\\\\expert2\\nbo\\Analytical and Bioanalytical Chemistry\\2016, Ahead Print.pdf
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10.
Инвентарный номер: нет.
   
   D 62


   
    Direct Modification of Quercetin by 6-Nitroazolo[1,5-a]Pyrimidines [Electronic resource] / E. B. Gorbunov, G. L. Rusinov, E. N. Ulomskii, O. S. Eltsov, V. L. Rusinov, V. G. Kartsev, V. N. Charushin, I. A. Khalymbadzha, O. N. Chupakhin // Chemistry of Natural Compounds. - 2016. - Vol. 52, № 4. - С. 708-710
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
DERIVATIVES -- INHIBITORS -- ANALOGS

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