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Journal of Chemistry
Volume 2016 (2016), Article ID 8406172, 6 pages
http://dx.doi.org/10.1155/2016/8406172
Research Article

New Catalytic Method for the Synthesis of 2,7-Dicycloalkyl-hexaazaperhydropyrenes

Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, 141 Prospekt Oktyabrya, Ufa 450075, Russia

Received 9 October 2016; Accepted 24 November 2016

Academic Editor: Gabriel Navarrete-Vazquez

Copyright © 2016 Elena Rakhimova et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. I. V. Borovlev and O. P. Demidov, “Diazapyrenes,” Chemistry of Heterocyclic Compounds, vol. 39, no. 11, pp. 1417–1442, 2003. View at Publisher · View at Google Scholar · View at Scopus
  2. I. V. Borovlev and O. P. Demidov, “Synthesis of aza-and polyazapyrenes (Review),” Chemistry of Heterocyclic Compounds, vol. 44, no. 11, pp. 1311–1327, 2008. View at Publisher · View at Google Scholar · View at Scopus
  3. A. V. Aksenov, I. V. Borovlev, I. V. Aksenova, S. V. Pisarenko, and D. A. Kovalev, “A new method for [c,d]pyridine peri-annelation: synthesis of azapyrenes from phenalenes and their dihydro derivatives,” Tetrahedron Letters, vol. 49, no. 4, pp. 707–709, 2008. View at Publisher · View at Google Scholar · View at Scopus
  4. M. Antoine, H. Bernard, N. Kervarec, and H. Handel, “Synthesis and NMR characterisation of new cyclam-glyoxal diamides,” Journal of the Chemical Society, Perkin Transactions 2, vol. 2, no. 3, pp. 552–555, 2002. View at Google Scholar · View at Scopus
  5. P. Neumann, A. Aumueller, and H. Trauth, US Pat. 4904779, Chem. Abstr., 112, P35899h, 1990.
  6. E. B. Rakhimova, R. A. Ismagilov, E. S. Meshcheryakova, L. M. Khalilov, A. G. Ibragimov, and U. M. Dzhemilev, “An efficient catalytic method for the synthesis of 2,7-dialkyl-2,3a,5a,7,8a,10a-hexaazaperhydropyrenes,” Tetrahedron Letters, vol. 55, no. 46, pp. 6367–6369, 2014. View at Publisher · View at Google Scholar · View at Scopus
  7. A. D. Andricopulo, L. A. Müller, V. C. Filho et al., “Analgesic activity of cyclic imides: 1,8-naphthalimide and 1,4,5,8-naphthalenediimide derivatives,” Il Farmaco, vol. 55, no. 4, pp. 319–321, 2000. View at Publisher · View at Google Scholar · View at Scopus
  8. S. G. Wakeham, “Azaarenes in recent lake sediments,” Environmental Science & Technology, vol. 13, no. 9, pp. 1118–1123, 1979. View at Publisher · View at Google Scholar · View at Scopus
  9. S. Roknić, L. Glavaš-Obrovac, I. Karner, I. Piantanida, M. Žinić, and K. Pavelić, “In vitro cytotoxicity of three 4,9-diazapyrenium hydrogensulfate derivatives on different human tumor cell lines,” Chemotherapy, vol. 46, no. 2, pp. 143–149, 2000. View at Publisher · View at Google Scholar · View at Scopus
  10. I. Steiner-Biocic, L. Glavaš-Obrovac, I. Karner et al., “4,9-diazapyrenium dications induce apoptosis in human tumor cells,” Anticancer Research, vol. 16, no. 6, pp. 3705–3708, 1996. View at Google Scholar · View at Scopus
  11. V. Balzani, S. J. Langford, F. M. Raymo, J. Fraser Stoddart, and M. Venturi, “Constructing molecular machinery: a chemically-switchable [2]Catenane,” Journal of the American Chemical Society, vol. 122, no. 14, pp. 3542–3543, 2000. View at Publisher · View at Google Scholar · View at Scopus
  12. J. Jazwinski, A. J. Blacker, J.-M. Lehn, M. Cesario, J. Guilhem, and C. Pascard, “Cyclo-bisintercalands: synthesis and structure of an intercalative inclusion complex, and anion binding properties,” Tetrahedron Letters, vol. 28, no. 48, p. 6060, 1987. View at Publisher · View at Google Scholar · View at Scopus
  13. P. J. Stang, B. Olenyuk, J. Fan, and A. M. Arif, “Combining ferrocenes and molecular squares: Self-assembly of heterobimetallic macrocyclic squares incorporating mixed transition metal systems and a main group element. Single-crystal X-ray structure of [Pt(dppf)(H2O)2][OTf]2,” Organometallics, vol. 15, no. 3, pp. 904–908, 1996. View at Publisher · View at Google Scholar · View at Scopus
  14. C. Chitwood and R. W. MacNamee, US Pat. 2345237, Chem. Abstr., 38, 4274, 1945.
  15. R. F. Borch and A. I. Hassid, “New method for the methylation of amines,” Journal of Organic Chemistry, vol. 37, no. 10, pp. 1673–1674, 1972. View at Publisher · View at Google Scholar · View at Scopus
  16. U. Wellmar, “Urea as leaving group in the synthesis of 3-(tert-butyl)perhydro-1,5,3-dithiazepine,” Journal of Heterocyclic Chemistry, vol. 35, no. 6, pp. 1531–1532, 1998. View at Publisher · View at Google Scholar · View at Scopus
  17. E. B. Rakhimova, R. A. Ismagilov, E. S. Meshcheryakova et al., “Synthesis of N-hydroxyalkyl-1,5,3-dithiazepanes based on amino alcohols,” Khim Geterotsikl Soedin, vol. 50, no. 5, pp. 782–787, 2014, Chemistry of Heterocyclic Compounds, vol. 50, no. 5, pp. 720–725, 2014 (English). View at Google Scholar
  18. E. B. Rakhimova, E. S. Meshcheryakova, L. M. Khalilov, A. G. Ibragimov, and U. M. Dzhemilev, “Efficient catalytic synthesis of (1,5,3-dithiazepan-3-yl)quinolines,” Zhurnal Organicheskoi Khimii, vol. 50, no. 11, pp. 1627–1630, 2014, English Translation: Russian Journal of Organic Chemistry, vol. 50, no. 11, pp. 1613–1616, 2014. View at Google Scholar
  19. E. B. Rakhimova, R. A. Ismagilov, L. M. Khalilov, R. A. Zainullin, A. G. Ibragimov, and U. M. Dzhemilev, “Efficient catalytic synthesis of N-cycloalkyl-1,5,3-dithiazepanes,” Russian Journal of Organic Chemistry, vol. 51, no. 7, pp. 951–956, 2015. View at Publisher · View at Google Scholar · View at Scopus
  20. S. P. Voronin, T. I. Gubina, S. A. Trushin, I. A. Markushina, and V. G. Kharchenko, “Mechanism of recyclization of furans to thiophenes and selenophenes under acid-catalysis conditions. 2. Kinetic investigations of the reaction of 2,5-dialkylfurans with hydrogen sulfide and hydrogen selenide in an anhydrous medium,” Khim Geterotsikl Soedin, vol. 25, no. 11, pp. 1458–1462, 1989, Chemistry of Heterocyclic Compounds, vol. 25, no. 11, pp. 1216–1220, 1989, (English). View at Google Scholar
  21. G. V. Mokrov, A. M. Likhosherstov, V. P. Lezina, T. A. Gudasheva, I. S. Bushmarinov, and M. Yu. Antipin, “Synthesis and selected properties of N-substituted pyrrolo[2,1-c]-1,3-diazacycloalkano[1,2-a]pyrazinones,” Izvestiya Akademii Nauk, Seriya Khimicheskaya, vol. 59, no. 6, pp. 1228–1239, 2010, Russian Chemical Bulletin, vol. 59, no. 6, pp. 1254–1266, 2010 (English). View at Google Scholar
  22. K. Krohn and S. Cludius-Brandt, “Acid-induced rearrangement reactions of α-hydroxy-1,3-dithianes,” Synthesis, no. 8, pp. 1344–1348, 2010. View at Publisher · View at Google Scholar · View at Scopus
  23. V. Y. Kukushkin and Y. N. Kukushkin, “ChemInform Abstract: Complex boron and aluminum hydrides in preparative coordination chemistry,” ChemInform, vol. 18, no. 3, article 288, 1987. View at Publisher · View at Google Scholar