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Pure Appl. Chem., 2004, Vol. 76, No. 9, pp. 1621-1631

http://dx.doi.org/10.1351/pac200476091621

SNH methodology and new approaches to condensed heterocyclic systems

V. N. Charushin and O. N. Chupakhin

Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, S. Kovalevskaya st. 20, 620219, Ekaterinburg, Russia

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  • Verbitskiy Egor V., Cheprakova Ekaterina M., Subbotina Julia O., Schepochkin Aleksandr V., Slepukhin Pavel A., Rusinov Gennady L., Charushin Valery N., Chupakhin Oleg N., Makarova Nadezhda I., Metelitsa Anatoly V., Minkin Vladimir I.: Synthesis, spectral and electrochemical properties of pyrimidine-containing dyes as photosensitizers for dye-sensitized solar cells. Dyes and Pigments 2014, 100, 201. <http://dx.doi.org/10.1016/j.dyepig.2013.09.006>
  • Atherton John H., Page Michael I., Sun Haifeng: Reaction kinetics in liquid ammonia up to 120°C: techniques and some solvolysis and substitution reactions. J. Phys. Org. Chem. 2013, 26, 1038. <http://dx.doi.org/10.1002/poc.3150>
  • Shchepochkin A. V., Chupakhin O. N., Charushin V. N., Rusinov G. L., Subbotina Yu. O., Slepukhin P. A., Budnikova Yu. G.: Stable σH-adducts in the reactions of the acridinium cation with heterocyclic N-nucleophiles. Russ Chem Bull 2013, 62, 773. <http://dx.doi.org/10.1007/s11172-013-0105-2>
  • Verbitskiy Egor V., Cheprakova Ekaterina M., Zhilina Ekaterina F., Kodess Mikhail I., Ezhikova Marina A., Pervova Marina G., Slepukhin Pavel A., Subbotina Julia O., Schepochkin Aleksandr V., Rusinov Gennady L., Chupakhin Oleg N., Charushin Valery N.: Microwave-assisted palladium-catalyzed C–C coupling versus nucleophilic aromatic substitution of hydrogen (SNH) in 5-bromopyrimidine by action of bithiophene and its analogues. Tetrahedron 2013, 69, 5164. <http://dx.doi.org/10.1016/j.tet.2013.04.062>
  • Varaksin M. V., Utepova I. A., Chupakhin O. N.: Direct C–C Coupling of Cyclic Aldonitrones with 1,2,4-Triazines Using S N H Reactions. Chem Heterocycl Comp 2012, 48, 1213. <http://dx.doi.org/10.1007/s10593-012-1124-x>
  • Verbitskiy Egor V., Cheprakova Ekaterina M., Slepukhin Pavel A., Kodess Mikhail I., Ezhikova Marina A., Pervova Marina G., Rusinov Gennady L., Chupakhin Oleg N., Charushin Valery N.: Combination of the Suzuki–Miyaura cross-coupling and nucleophilic aromatic substitution of hydrogen () reactions as a versatile route to pyrimidines bearing thiophene fragments. Tetrahedron 2012, 68, 5445. <http://dx.doi.org/10.1016/j.tet.2012.04.095>
  • Varaksin Mikhail V., Utepova Irina A., Chupakhin Oleg N., Charushin Valery N.: Palladium(II)-Catalyzed Oxidative C–H/C–H Coupling and Eliminative SNH Reactions in Direct Functionalization of Imidazole Oxides with Indoles. J. Org. Chem. 2012, 77, 9087. <http://dx.doi.org/10.1021/jo301618b>
  • Kovalev I. S., Rusinov V. L., Chupakhin O. N.: Reaction of 2-pyridyllithium with azine N-oxides. Simple and convenient method for the synthesis of 2,2′-bipyridine 1-oxide and 2,2′:6′,2″:6″2′″-tetrapyridine 1′-oxide. Chem Heterocycl Compd 2009, 45, 176. <http://dx.doi.org/10.1007/s10593-009-0247-1>
  • Verbitskiy E. V., Berezin M. V., Slepukhin P. A., Rusinov G. L., Charushin V. N.: σH-Adducts of N-alkylpyrazinium and quinoxalinium salts with nucleophiles. The 1H and 13C NMR spectra and the crystal structures of P-adducts. Russ Chem Bull 2009, 58, 176. <http://dx.doi.org/10.1007/s11172-009-0027-1>
  • L. Rusinov Gennadiy, V. Verbitskiy Egor, A. Slepukhin Pavel, N. Zabelina Olga, I. Kodess Mikhail, A. Ezhikova Marina, N. Charushin Valeriy, N. Chupakhin Oleg: Reactions of Radicals Generated from 1-Ethyl-1,4-diazinium-salts: Addition to the C-C Triple Bond versus Dimerization. HETEROCYCLES 2009, 78, 2315. <http://dx.doi.org/10.3987/COM-09-11734>
  • Verbitskiy E. V., Slepukhin P. A., Rusinov G. L., Charushin V. N.: Transformations of C-adducts of 1,4-diazinium salts with dicarbonyl compounds into polycyclic systems. Russ Chem Bull 2008, 57, 652. <http://dx.doi.org/10.1007/s11172-008-0102-z>
  • Ovcharenko V. I., Chupakhin O. N., Kovalev I. S., Tretyakov E. V., Romanenko G. V., Stass D. V.: S N H Reaction of lithiated nitronyl nitroxide with quinoline N-oxide. Russ Chem Bull 2008, 57, 2227. <http://dx.doi.org/10.1007/s11172-008-0309-z>
  • Chupakhin Oleg N., Utepova Irina A., Kovalev Igor S., Rusinov Vladimir L., Starikova Zoya A.: Direct C–C Coupling of Ferrocenyllithium and Azaheterocycles by Nucleophilic Substitution of Hydrogen – Synthesis of Mono- and 1,1′-Diazinylferrocenes. Eur J Org Chem 2007, 2007, 857. <http://dx.doi.org/10.1002/ejoc.200600821>
  • Charushin V. N., Chupakhin O. N.: New methodologies of organic synthesis. Her Russ Acad Sci 2007, 77, 227. <http://dx.doi.org/10.1134/S1019331607030033>
  • Zhumabaeva G. A., Kotovskaya S. K., Perova N. M., Charushin V. N., Chupakhin O. N.: Tandem of nucleophilic substitution of hydrogen and cyclocondensation with participation of nitro group in the synthesis of fluorine-containing 3-amino-1,2,4-benzotriazines. Russ Chem Bull 2006, 55, 1243. <http://dx.doi.org/10.1007/s11172-006-0406-9>
  • Charushin Valery N., Chupakhin Oleg N.: SNH Methodology and New Approaches to Condensed Heterocyclic Systems. ChemInform 2005, 36. <http://dx.doi.org/10.1002/chin.200509263>
  • Slepukhin P. A., Mochul’skaya N. N., Sidorova L. P., Rusinov G. L., Ezhikova M. A., Kodess M. I., Kazheva O. N., Chekhlov A. N., D’yachenko O. A., Charushin V. N.: Nitroalkyl-substituted tetrahydropyrazines in syntheses of azapolycyclic compounds. Russ Chem Bull 2005, 54, 2197. <http://dx.doi.org/10.1007/s11172-006-0096-3>
  • Boguslavskii A. M., Ponizovskii M. G., Kodess M. I., Charushin V. N.: Ring-Chain Transformations of Dihydroisoxazolo[4,5-b]quinoxaline. Russ J Org Chem 2005, 41, 1377. <http://dx.doi.org/10.1007/s11178-005-0350-4>