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    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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   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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   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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   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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   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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   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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   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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    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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   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.

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   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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11.

Инвентарный номер: нет.

   D 64


    Dithienoquinazolines – A Convenient Synthesis by the Oxidative Photocyclization of 4,5-Dithienyl-Substituted Pyrimidines and Their Photophysical Properties [Electronic resource] / E. V. Verbitskiy, P. A. Slepukhin, M. S. Valova, E. M. Cherprakova, A. V. Schepochkin, G. L. Rusinov, V. N. Charushin // European Journal of Organic Chemistry. - 2014. - № 36. - С. 8133-8141

ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
DITHIENOQUINAZOLINES -- PYRIMIDINES -- PHOTOPHYSICAl PROPERTIES
Аннотация: A convenient route to a new class of thienoacene systems bearing a fused pyrimidine ring is presented along with their optoelectronic properties. The photophysical and electrochemical properties of these newly developed thieno-aza-acenes have been investigated by UV/Vis absorption and photoluminescence spectrophotometry and cyclic voltammetry, and some crystal structures have also been determined.

\\\\expert2\\nbo\\European Journal of Organic Chemistry\\2014, № 36. p.8133-8141.pdf
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12.

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   F 70


    Fluoro-containing Heterocycles: V. Cyclization of 3-Azolylamino-2-polyfluorobenzoylacrylates [Electronic resource] / G. N. Lipunova, E. V. Nosova, M. I. Kodess, V. N. Charushin, Yu. A. Rozin, O. M. Chasovskikh // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2001. - Vol. 37, № 4. - P570-576

ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: The heating of ethyl 3-azolylamino-2-polyfluorobenzoylacrylates in acetonitrile in the presence of KF gave rise to derivatives of 1-azolyl-substituted quinolones or azolo[1,5-a]pyrimidines??

\\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2001, 37 (4), 570.pdf
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13.

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   H 62


    Heteroacenes Bearing the Pyrimidine Scaffold: Synthesis, Photophysical and Electrochemical Properties / E. V. Verbitskiy [и др.] // European Journal of Organic Chemistry. - 2016. - Vol. 1260, № 7. - С. 1420-1428. - Bibliogr. : p. 1427-1428 (17 ref.)

ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
PYRIMIDINES -- SYNTHESIS -- ELECTROCHEMICAL PROPERTIES

\\\\expert2\\NBO\\European Journal of Organic Chemistry\\2016, v. 2016, p. 1420.pdf
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14.

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   M 65


    Microwave-assisted palladium-catalyzed C–C coupling versus nucleophilic aromatic substitution of hydrogen (SNH) in 5-bromopyrimidine by action of bithiophene and its analogues [Электронный ресурс] / E. V. Verbitskiy, E. M. Cheprakova, E. F. Zhilina, M. I. Kodess, M. A. Ezhikova, M. G. Pervova, P. A. Slepukhin, V. N. Charushin // Tetrahedron. - 2013. - Vol.69, №25. - P5164-5172

ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
C–H BOND ACTIVATIONS -- PYRIMIDINES -- PALLADIUM
Аннотация: 5-Bromopyrimidine reacts with 2,2′-bithiophene, [2,2′:5′,2″]terthiophene and 2-phenylthiophene in the presence of a palladium catalyst to give 5-(het)aryl substituted pyrimidines due to the palladium-catalyzed aryl–aryl C–C coupling. However 5-bromo-4-(het)aryl-pyrimidines have been prepared from the same starting materials through the SNH-reaction catalyzed by a Lewis acid. Conditions for both types of reactions were optimized. All components of the reaction mixtures, including by-products, have been elucidated by gas–liquid chromatography/mass-spectrometry. Evidence for the structure of 4- and 5-bithiophenyl-substituted pyrimidines has first been obtained by means of X-ray crystallography analysis. Molecular orbital calculations (TDDFT), as well as the redox and optical measurements for all new compounds have also been performed

\\\\Expert2\\NBO\\Tetrahedron\\2013, v. 68, p. 5164.pdf
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15.

Инвентарный номер: нет.

   M 65


    Microwave-assisted synthesis and evaluation of antibacterial activity of novel 6-fluoroaryl-[1,2,4]triazolo[1,5-a]pyrimidines. / E. V. Verbitskiy [и др.] // ARKIVOC. - 2016. - Vol. V. - С. 268-278. - Bibliogr. : p. 276-278 (28 ref.)

ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
SYNTHESIS -- PYRIMIDINES -- ANTIBACTERIAL ACTIVITY

\\\\expert2\\NBO\\ARKIVOC\\2016, p.268-278.pdf
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16.

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   N 52


    New 2H-[1,2,3]triazolo[4,5-e][1,2,4]triazolo[1,5-a]pyrimidine derivatives as luminescent fluorophores for detection of nitroaromatic explosives [Electronic resource] / E. V. Verbitskiy, E. B. Gorbunov, A. A. Baranova, K. I. Ludovik, K. O. Khokhlov, E. M. Cheprakova, G. A. Kim, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin // Tetrahedron. - 2016. - Vol. 72, № 32. - С. 4954-4961

ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
CARBAZOLE -- NITROAROMATIC EXPLOSIVES -- TRIPHENYLAMINE
Аннотация: A number of D-pi-A type dyes on the basis of new 2H[1,2,3]triazolo[4,5-e][1,2,4]triazolo[1,5-a]pyrimidines, bearing various electron-donating carbazole and triphenylamine fragments, have been studied as sensing fluorophores. Fluorescence studies have demonstrated that emission spectra of these compounds in acetonitrile are sensitive to the presence of nitroaromatic explosives, such as 2,4-dinitroanisole (DNAN), picric acid (PA), styphnic acid (SA), 1,3,5-triethoxy-2,4,6-trinitrobenzene (TETNB), 2,4-dinitrotoluene (DNT), 2,4,6-trinitrotoluene (TNT) and nitrobenzene (NB). Detection limits of fluorophores for DNAN, PA, SA, TETNB, DNT and TNT proved to be in the range from 4.82x10(-1) to 2.96x10(-3) mol/L, 2.10x10(-3) to 5.98x10(-5) mol/L, 1.26x10(-1) to 2.02x10(-4) mol/L, 1.58 x 10(-1) to 1.62x10(-3) mol/L, 1.26x10(-1) to 5.61x10(-4) mol/L and 9.01x10(-2) to 2.77x10(-3) mol/L, respectively. Selective fluorescence quenching response, including a sharp color change under UV irradiation (especially for PA, SA and DNT), makes these compounds promising fluorescence chemosensors for nitroaromatic explosives

\\\\expert2\\NBO\\Tetrahedron\\2016, v. 72 , p. 4954-4961.pdf
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17.

Инвентарный номер: нет.

   N 52


    New 4,5-di(hetero)arylpyrimidines as sensing elements for detection of nitroaromatic explosives in vapor phase / E. V. Verbitskiy, A. A. Baranova, K. I. Lugovik, K. O. Khokhlov, E. M. Cheprakova, M. Z. Shafikov, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin // Dyes and Pigments. - 2017. - Vol. 137. - P360-371

ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
FLUORESCENCE QUENCHING -- NITROAROMATIC EXPLOSIVES -- TRIPHENYLAMINES -- CARBAZOLES -- PYRIMIDINES
Аннотация: A series of D–π–A–π–D type dyes based on pyrimidines, bearing thiophene linkers, have been studied as sensing fluorophores. Fluorescence studies have demonstrated that the emission of all derivatives is sensitive to the presence of 2,4,6-trinitrotoluene (TNT) and other nitroaromatic compounds (NACs), in their acetonitrile solutions. The detection limits of fluorophores to NACs proved to be in the range from 10−4 to 10−6 mol/L. The time-resolved fluorescence measurements and theoretical investigation into the quenching mechanism in the presence of fluorophore has been performed. The two types of sensor prototypes for handheld sniffer «Nitroscan» (Plant «Promautomatika», Ekaterinburg, Russia) on the basis of non-woven dry wipe and spunlace non-woven fabric with various quantities of the most sensitive fluorophore have been fabricated. The reusable, reversible and sensitive response of the designed prototypes to NACs enables one to qualify these compounds as promising fluorescent sensory materials for detection of NACs.

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18.

ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
4,5-DI(HETERO)ARYLPYRIMIDINES -- NITROAROMATIC EXPLOSIVES -- VAPOR PHASE
Аннотация: A series of D–π–A–π–D type dyes based on pyrimidines, bearing thiophene linkers, have been studied as sensing fluorophores. Fluorescence studies have demonstrated that the emission of all derivatives is sensitive to the presence of 2,4,6-trinitrotoluene (TNT) and other nitroaromatic compounds (NACs), in their acetonitrile solutions. The detection limits of fluorophores to NACs proved to be in the range from 10−4 to 10−6 mol/L. The time-resolved fluorescence measurements and theoretical investigation into the quenching mechanism in the presence of fluorophore has been performed. The two types of sensor prototypes for handheld sniffer «Nitroscan» (Plant «Promautomatika», Ekaterinburg, Russia) on the basis of non-woven dry wipe and spunlace non-woven fabric with various quantities of the most sensitive fluorophore have been fabricated. The reusable, reversible and sensitive response of the designed prototypes to NACs enables one to qualify these compounds as promising fluorescent sensory materials for detection of NACs.

\\\\expert2\\nbo\\Dyes and Pigments\\2016, v. 137, p.360-371.pdf
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19.

Инвентарный номер: нет.

   N 52


    New V-shaped push-pull systems based on 4,5-di(hetero)aryl substituted pyrimidines: their synthesis and application to the detection of nitroaromatic explosives. / E. V. Verbitskiy, A. A. Baranova, K. I. Lugovik, K. O. Khokhlov, E. M. Cheprakova, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin // ARKIVOC. - 2016. - Vol. III. - С. 360-373. - Bibliogr. : p. 370-373 (50 ref.)

ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
PYRIMIDINES -- SYNTHESIS -- NITROAROMATIC EXPLOSIVES

\\\\expert2\\NBO\\ARKIVOC\\2016, p.360-373.pdf
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20.

Инвентарный номер: нет.

   O-57


    One-pot synthesis of 6H-pyrrolo[2,3-e[1,2,4]triazolo[1,5-a]pyrimidines on the basis of delta H-adducts of 6-Nitro[1,2,4]triazolo[1,5-a]pyrimidine with carbonyl compounds [Electronic resource] / E. B. Gorbunov, G. L. Rusinov, R. I. Ishmetova, V. N. Charushin, O. N. Chupakhin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2008. - Vol. 44, № 1. - P128-132

ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: Aromatic, heteroaromatic, and aliphatic carbonyl compounds reacted with 6-nitro[1,2,4]triazolo[1,5-a]pyrimidine in the presence of a base to give stable ?H-adducts at C7. Reduction of the nitro group in the latter is accompanied by tandem autoaromatization of the azine ring and intramolecular cyclocondensation with formation of the corresponding 6H-pyrrolo[2,3-e][1,2,4]triazolo[1,5-a]pyrimidines

\\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2008, 44 (1), 128.pdf
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