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Synthesis of novel polycyclic heterosystems from 5-nitro[1,2,5]selenadiazolo[3,4-e]benzofuroxans

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Chemistry of Heterocyclic Compounds Aims and scope

A method for the preparation of 5-nitro[1,2,5]selenadiazolo[3,4-e]benzofuroxan has been developed. Employing the reactivity of this compound in pericyclic (4+2) and (3+2) cycloaddition reactions as a dienophile or dipolarophile (at the C=C–NO2 bond) with a heterodiene (fragment C=C–N(O)=O) representatives of novel types of fused polycyclic heterosystems were synthesized.

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References

  1. (a) Ananikov, V. P.; Khokhlova, E. A.; Egorov, M. P.; Sakharov, A. M.; Zlotin, S. G.; Kucherov, A. V.; Kustov, L. M.; Gening, M. L.; Nifantiev, N. E. Mendeleev Commun. 2015, 25, 75. (b) Zlotin, S. G.; Churakov, A. M.; Luk'yanov, O. A.; Makhova, N. N.; Sukhorukov, A. Yu.; Tartakovsky, V. A. Mendeleev Commun. 2015, 25, 399.

  2. (a) Bastrakov, M. A.; Starosotnikov, A. M.; Kachala, V. V.; Fedyanin, I. V.; Shevelev, S. A. Asian J. Org. Chem. 2015, 4, 146. (b) Bastrakov, M. A.; Starosotnikov, A. M.; Fedyanin, I. V.; Kachala, V. V.; Shevelev, S. A. Mendeleev Commun. 2014, 24, 203. (c) Bastrakov, M. A.; Starosotnikov, A. M.; Kachala, V. V.; Dalinger, I. L.; Shevelev, S. A. Chem. Heterocycl. Compd. 2015, 51, 496. [Khim. Geterotsikl. Soedin. 2015, 51, 496.] (d) Steglenko, D. V.; Shevelev, S. A.; Kletskii, M. E.; Burov, O. N.; Lisovin, A. V.; Starosotnikov, A. M.; Morozov, P. G.; Kurbatov, S. V.; Minkin, V. I.; Bastrakov, M. A. Chem. Heterocycl. Compd. 2015, 51, 845. [Khim. Geterotsikl. Soedin. 2015, 51, 845.] (e) Starosotnikov, A. M.; Bastrakov, M. A.; Pavlov, A. A.; Fedyanin, I. V.; Dalinger, I. L.; Shevelev, S. A. Mendeleev Commun. 2016, 26, 217.

  3. (a) Cerecetto, H.; Porcal, W. Mini-Rev. Med. Chem. 2005, 5, 57. (b) Cerecetto, H.; Gonzalez, M. Top. Heterocycl. Chem. 2007, 10, 265. (c) Jovene, C.; Chugunova, E. A.; Goumont, R. Mini-Rev. Med. Chem. 2013, 13, 1089.

  4. Korolev, S. P.; Kondrashina, O. V.; Druzhilovsky, D. S.; Starosotnikov, A. M.; Dutov, M. D.; Bastrakov, M. A.; Dalinger, I. L.; Filimonov, D. A.; Shevelev, S. A.; Poroikov, V. V.; Agapkina, Y. Y.; Gottikh, M. B. Acta Naturae 2013, 5, 65.

    Google Scholar 

  5. Ghosh, P. B.; Everitt, B. J. J. Med. Chem. 1974, 17, 203.

    Article  CAS  Google Scholar 

  6. Fershtat, L. L.; Epishina, M. A.; Kulikov, A. S.; Makhova, N. N. Mendeleev Commun. 2015, 25, 36. (b) Fershtat, L. L.; Epishina, M. A.; Kulikov, A. S.; Struchkova, M. I.; Makhova, N. N. Chem. Heterocycl. Compd. 2015, 51, 176. [Khim. Geterotsikl. Soedin. 2015, 51, 176.] (c) Fershtat, L. L.; Larin, A. A.; Epishina, M. A.; Ovchinnikov, I. V.; Kulikov, A. S.; Ananyev, I. V.; Makhova, N. N. RSC Adv. 2016, 6, 31526. (d) Fershtat, L. L.; Epishina, M. A.; Ovchinnikov, I. V.; Kachala, V. V.; Makhova, N. N. Chem. Heterocycl. Compd. 2015, 51, 754. [Khim. Geterotsikl. Soedin. 2015, 51, 754.]

  7. (a) Shealy, Y. F.; Clayton, J. D.; Dixon, G. J.; Dulmadge, E. A.; Pittillo, R. F.; Hunt, D. E. Biochem. Pharmacol. 1966, 15, 1610. (b) Huang, X.-C.; Zheng, J.-S.; Chen, T.-F.; Zhang, Y.-B.; Luo, Y.; Zheng, W.-J. Chem. J. Chinese Univ. 2012, 33, 976. (c) Plano, D.; Moreno, E.; Font, M.; Encío, I.; Palop, J. A.; Sanmartin, C. Arch. Pharm. Weinheim, Ger. 2010, 10, 680.

  8. (a) Bastrakov, M. A.; Starosotnikov, A. M.; Shakhnes, A. Kh.; Shevelev, S. A. Russ. Chem. Bull. 2008, 57, 1539 [Izv. Akad. Nauk, Ser. Khim. 2008, 1508.] (b) Bastrakov, M. A.; Starosotnikov, A. M.; Kachala, V. V.; Glukhov, I. V.; Shevelev, S. A. Russ. Chem. Bull. 2009, 58, 414. [Izv. Akad. Nauk, Ser. Khim. 2009, 407.] (c) Bastrakov, M. A.; Starosotnikov, A. M.; Glukhov, I. V.; Shevelev, S. A. Russ. Chem. Bull. 2009, 58, 426. [Izv. Akad. Nauk, Ser. Khim. 2009, 418.]

  9. Elvidge, J. A.; Newbold, G. T.; Percival A.; Senciall, I. R. J. Chem. Soc. 1965, 5119.

  10. Lakhdar, S.; Goumont, R.; Boubaker, T.; Mokhtari, M.; Terrier, F. Org. Biomol. Chem. 2006, 4, 1910. (b) Shevelev, S. A.; Starosotnikov, A. M. Chem. Heterocycl. Compd. 2013, 49, 92. [Khim. Geterotsikl. Soedin. 2013, 102.] (c) Terrier, F. Modern Nucleophilic Aromatic Substitution; Wiley, 2013.

  11. (a) Bastrakov, M. A.; Starosotnikov, A. M., Pechenkin, S. Yu.; Kachala, V. V.; Glukhov, I. V.; Shevelev, S. A. J. Heterocycl. Chem. 2010, 47, 893. (b) Konstantinova, L. S.; Bastrakov, M. A.; Starosotnikov, A. M.; Glukhov, I. V.; Lysov, K. A.; Rakitin, O. A.; Shevelev, S. A. Mendeleev Commun. 2010, 20, 353.

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Correspondence to Maxim A. Bastrakov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(9), 690–693

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Bastrakov, M.A., Starosotnikov, A.M., Pavlov, A.A. et al. Synthesis of novel polycyclic heterosystems from 5-nitro[1,2,5]selenadiazolo[3,4-e]benzofuroxans. Chem Heterocycl Comp 52, 690–693 (2016). https://doi.org/10.1007/s10593-016-1950-3

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  • DOI: https://doi.org/10.1007/s10593-016-1950-3

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