Chemistry of Heterocyclic Compounds

, Volume 52, Issue 10, pp 797–802 | Cite as

Heterocyclic analogs of 5,12-naphtacenequinone 13*. Synthesis of 4,11-diaminoanthra[2,3-b]furan-5,10-diones and sulfur-containing analogs

  • Alexander S. Tikhomirov
  • Eugeny E. Bykov
  • Yury N. Luzikov
  • Alexander M. Korolev
  • Andrey E. Shchekotikhin
Article
First Online:
Received:
Accepted:

We have developed an effective method for the synthesis of 4,11-diaminoanthra[2,3-b]furan-5,10-dione and 4,11-diaminoanthra[2,3-b]-thiophene-5,10-dione derivatives based on the substitution of 4,11-alkoxy groups with n-butylamine and subsequent oxidative dealkylation of n-butylamino groups via treatment with tetrabutylammonium hydroxide in DMSO.

Keywords

amino derivatives hetarene-fused anthracene-9,10-diones DFT calculations oxidative dealkylation 
This is a preview of subscription content, log in to check access.

Notes

This study was supported by the Russian Foundation for Basic Research (project No. 16-33-00908 mol_a).

Supplementary material

10593_2016_1968_MOESM1_ESM.pdf (1.6 mb)
ESM 1 (PDF 1607 kb)

References

  1. 1.
    Tikhomirov, A. S.; Shchekotikhin, A. E.; Luzikov, Yu. N.; Korolev, A. M.; Preobrazhenskaya, M. N. Chem. Heterocycl. Compd. 2014, 50, 271. [Khim. Geterotsikl. Soedin. 2014, 298.]Google Scholar
  2. 2.
    Stepanov, A. A.; Gornostaev, L. M.; Vasilevsy, S. F.; Arnold, E. V.; Mamatyuk, V. I.; Fadeev, D. S.; Gold, B.; Alabugin, I. V. J. Org. Chem. 2011, 76, 8737.CrossRefGoogle Scholar
  3. 3.
    Zvarich, V. I.; Stasevich, M. V.; Lunin, V. V.; Vovk, M. V.; Novikov, V. P. Chem. Heterocycl. Compd. 2016 , 52, 421. [Khim. Geterotsikl. Soedin. 2016, 52, 421.]Google Scholar
  4. 4.
    Shaikh, A. M.; Sharma, B. K.; Kamble, R. M. Chem. Heterocycl. Compd. 2016, 52, 110. [Khim. Geterotsikl. Soedin. 2016, 52, 110.]Google Scholar
  5. 5.
    Cogoi, S.; Shchekotikhin, A. E.; Membrino, A.; Sinkevich, Y. B.; Xodo, L. E. J. Med. Chem. 2013, 56, 2764.CrossRefGoogle Scholar
  6. 6.
    Shchekotikhin, A. E.; Glazunova, V. A.; Dezhenkova, L. G.; Shevtsova, E. K.; Traven', V. F.; Balzarini, J.; Huang, H.-S.; Shtil, A. A.; Preobrazhenskaya, M. N. Eur. J. Med. Chem. 2011, 46, 423.Google Scholar
  7. 7.
    Tikhomirov, A. S.; Shchekotikhin, A. E.; Lee, Y.-H.; Chen, Y.-A.; Yeh, C.-A.; Tatarskiy, V. V., Jr.; Dezhenkova, L. G.; Glazunova, V. A.; Balzarini, J.; Shtil, A. A.; Preobrazhenskaya, M. N.; Chueh, P. J. J. Med. Chem. 2015, 58, 9522.CrossRefGoogle Scholar
  8. 8.
    Gorelik, M. V.; Mishina E. V. Russ. J. Org. Chem. 1983, 19, 1892. [Zh. Org. Khim. 1983, 2185.]Google Scholar
  9. 9.
    Al-Saleh, B.; Abdelkhalik, M. M.; El-Apasery, M. A.; Elnagdi, M. H. J. Chem. Res. 2005, 1, 23.CrossRefGoogle Scholar
  10. 10.
    Al-Saleh, B.; El-Apasery, M. A.; Hilmy, N. M.; Elnagdi, M. H. J. Heterocycl. Chem. 2006, 43, 1575.CrossRefGoogle Scholar
  11. 11.
    Gundermann, K.-D.; Klockenbring, G.; Röker, C.; Brinkmeyer, H. Justus Liebigs Ann. Chem. 1976, 10, 1873.CrossRefGoogle Scholar
  12. 12.
    Shchekotikhin, A. E.; Luzikov, Yu. N.; Buyanov, V. N.; Preobrazhenskaya, M. N. Chem. Heterocycl. Compd. 2006, 42, 746. [Khim. Geterotsikl. Soedin. 2006, 854.]Google Scholar
  13. 13.
    Dzieduszycka, M.; Martelli, S.; Arciemiuk, M.; Bontemps-Gracz, M. M.; Kupieca, A.; Borowski, E. Bioorg. Med. Chem. 2002, 10, 1025.CrossRefGoogle Scholar
  14. 14.
    Bu, X.; Deady, L. W.; Finlay, G. J.; Baguley, B. C.; Denny, W. A. J. Med. Chem. 2001, 44, 2004.CrossRefGoogle Scholar
  15. 15.
    Perry, P. J.; Reszka, A. P.; Wood, A. A.; Read, M. A.; Gowan, S. M.; Dosanjh, H. S.; Trent, J. O.; Jenkins, T. C.; Kelland, L. R.; Neidle, S. J. Med. Chem. 1998, 41, 4873.CrossRefGoogle Scholar
  16. 16.
    Ilyinsky, N. S.; Shchyolkina, A. K.; Borisova, O. F.; Mamaeva, O. K.; Zvereva, M. I.; Azhibek, D. M.; Livshits, M. A.; Mitkevich, V. A.; Balzarini, J.; Sinkevich, Yu. B.; Luzikov, Yu. N.; Dezhenkova, L. G.; Kolotova, E. S.; Shtil, A. A.; Shchekotikhin, A. E.; Kaluzhny, D. N. Eur. J. Med. Chem. 2014, 85, 605.Google Scholar
  17. 17.
    Morley, J. O.; Furlong, P. J. Org. Biomol. Chem. 2006, 4, 4005.Google Scholar
  18. 18.
    Agnès, A. J. Chem. Soc., Perkin Trans. 2 1989, 311.Google Scholar
  19. 19.
    Tikhomirov, A. S.; Shchekotikhin, A. E.; Luzikov, Yu. N.; Korolev, A. M.; Preobrazhenskaya, M. N. Tetrahedron 2014, 70, 8062.Google Scholar
  20. 20.
    Shchekotikhin, A. E.; Shevtsova, E. K.; Traven', V. F. Russ. J. Org. Chem. 2007, 43, 1686.Google Scholar
  21. 21.
    Sinkevich, Yu. B.; Shchekotikhin, A. E.; Luzikov, Yu. N.; Buyanov, V. N.; Kovalenko, L. V. Chem. Heterocycl. Compd. 2007, 43, 1252. [Khim. Geterotsikl. Soedin. 2007, 1478.]Google Scholar
  22. 22.
    Tikhomirov, A. S.; Shchekotikhin, A. E.; Luzikov, Yu. N.; Korolev, A. M.; Preobrazhenskaya, M. N. Chem. Heterocycl. Compd. 2012, 47, 1206. [Khim. Geterotsikl. Soedin., 2011, 1464.]Google Scholar
  23. 23.
    Shchekotikhin, A. E.; Baberkina, E. P.; Turchin, K.F.; Buyanov, V. N.; Suvorov, N. N. Chem. Heterocycl. Compd. 2000, 36, 1284. [Khim. Geterotsikl. Soedin. 1999, 1491.]Google Scholar
  24. 24.
    Shchekotikhin, A. E.; Silaev, D. A.; Baberkina, E. P.; Makarov, I. G.; Buyanov, V. N.; Suvorov, N. N. Chem. Heterocycl. Compd. 2002, 38, 543. [Khim. Geterotsikl. Soedin. 2002, 623.]Google Scholar
  25. 25.
    Nguyen, M. T.; Chandra, A. K.; Zeegers-Huyskens, T. J. Chem. Soc., Faraday Trans. 1998, 94, 1277.Google Scholar
  26. 26.
    Verdolino, V.; Cammi, R.; Munk, B. H.; Schlegel, H. B. J. Phys. Chem. B 2008, 112, 16860.CrossRefGoogle Scholar
  27. 27.
    Tay, F.; Duran, M.; Demirayak, S. Indian J. Chem., Sec. B 2014, 53, 102.Google Scholar
  28. 28.
    Elguero, J.; Alkorta, I.; Claramunt, R. M.; Cabildo, P.; Cornago, P.; Ángeles Farrán, M.; Ángeles García, M.; López, C.; Pérez-Torralba, M.; Santa María, D.; Sanz D. Chem. Heterocycl. Compd. 2013, 49, 177. [Khim. Geterotsikl. Soedin. 2013, 191.]Google Scholar
  29. 29.
    Becke, A. D. J. Chem. Phys. 1993, 98, 5648.CrossRefGoogle Scholar
  30. 30.
    Cossi, M.; Barone, V.; Mennucci, B.; Tomasi, J. Chem. Phys. Lett. 1998, 286, 253.CrossRefGoogle Scholar
  31. 31.
    Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09; Gaussian, Inc.: Wallingford CT, 2009.Google Scholar

Copyright information

© Springer Science+Business Media New York 2016

Authors and Affiliations

  • Alexander S. Tikhomirov
    • 1
    • 2
  • Eugeny E. Bykov
    • 1
  • Yury N. Luzikov
    • 1
  • Alexander M. Korolev
    • 1
  • Andrey E. Shchekotikhin
    • 1
    • 2
  1. 1.G. F. Gause Institute of New AntibioticsMoscowRussia
  2. 2.D. Mendeleev University of Chemical Technology of RussiaMoscowRussia

Personalised recommendations