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3-Nitropyrimido[1,2-a]benzimidazol-4-ones: synthesis and study of alkylation reaction

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Chemistry of Heterocyclic Compounds Aims and scope

The reactions of benzimidazol-2-amines with ethyl 3-ethoxy-2-nitroacrylate were used to synthesize a series of pyrimido[1,2-a]-benzimidazoles. An alkylation reaction of the obtained compounds was studied.

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References

  1. Swan, S. K.; Smith, W. B.; Marbury, T. C.; Schumacher, M.; Dougherty, C.; Mico, B. A.; Villano, S. A. J. Clin. Pharmacol. 2007, 47, 209.

    Article  CAS  Google Scholar 

  2. Chou, S.; Marousek, G. I. Antimicrob. Agents Chemother. 2006, 50, 3470.

    Article  CAS  Google Scholar 

  3. Chupakhin, O. N.; Charushin, V. N.; Rusinov, V. L.; Ulomskii, E. N.; Kotovskaya, S. K.; Kiselev, O. I.; Deeva, E. G.; Savateev, K. V.; Borisov, S. S. RU patent 2529487, 2014.

  4. Dalla Via, L.; Gia, O.; Magno, S. M.; Da Settimo, A.; Marini, A. M.; Primofiore, G.; Da Settimo, F.; Salerno, S. Farmaco 2001, 56, 159.

    Article  CAS  Google Scholar 

  5. Abdel-monem, A.-h. A. Arch. Pharm. Res. 2007, 30, 678.

    Article  Google Scholar 

  6. Da Settimo, A.; Primofiore, G.; Da Settimo, F.; Marini, A. M.; Taliani, S.; Salerno, S.; Dalla Via, L. J. Heterocycl. Chem. 2003, 40, 1091.

    Article  Google Scholar 

  7. Starcevic, K.; Kralj, M.; Ester, K.; Karminski-Zamola, G. Heterocycles 2007, 71, 647.

    Article  CAS  Google Scholar 

  8. Vaidyanathan, V. G.; Villalta, P. W.; Sturla, S. J. Chem. Res. Toxicol. 2007, 20, 913.

    Article  CAS  Google Scholar 

  9. Chiba, T.; Shigeta, S.; Numazaki, Y. Biol. Pharm. Bull. 1995, 18, 1081.

    Article  CAS  Google Scholar 

  10. Gupta, S. P.; Chem. Rev. 1994, 94, 1507.

    Article  CAS  Google Scholar 

  11. Kouadri, Y.; Ouahrani, M. R.; Missaoui, B. E.; Chebrouk, F.; Gherraf, N. Asian J. Chem. 2015, 27, 3675.

    Article  CAS  Google Scholar 

  12. Ishida, J.; Wang, H.-K.; Oyama, M.; Cosentino, M. L.; Hu, C.-Q.; Lee, K.-H. J. Nat. Prod. 2001, 64, 958.

    Article  CAS  Google Scholar 

  13. Leonard, N. J.; Morrice, A. G.; Sprecker, M. A. J. Org. Chem. 1975, 40, 356.

    Article  CAS  Google Scholar 

  14. Baraldi, P. G.; Tabrizi, M. A.; Gessi, S.; Borea, P. A. Chem. Rev. 2008, 108, 238.

    Article  CAS  Google Scholar 

  15. Bumagin, N. A.; Zelenkovskii, V. M.; Kletskov, A. V.; Petkevich, S. K.; Dikusar, E. A.; Potkin, V. I. Russ. J. Gen. Chem. 2016, 86, 68. [Zh. Obshch. Khim. 2016, 86, 75.]

  16. Bumagin, N. A.; Potkin, V. I. Russ. Chem. Bull., Int. Ed. 2016, 65, 321. [Izv. Akad. Nauk, Ser. Khim. 2016, 321.]

  17. Bumagin, N. A. Catal. Commun. 2016, 79, 17.

    Article  CAS  Google Scholar 

  18. Potkin, V. I.; Bumagin, N. A.; Zelenkovskii, V. M.; Petkevich, S. K.; Livantsov, M. V.; Golantsov, N. E. Russ. J. Gen. Chem. 2014, 84, 1782. [Zh. Obshch. Khim. 2014, 84, 1546.]

  19. Bumagin, N. A.; Petkevich, S. K.; Kletskov, A. V.; Livantsov, M. V.; Golantsov, N. E.; Potkin, V. I. Chem. Heterocycl. Compd. 2014, 49, 1515. [Khim. Geterotsikl. Soedin. 2013, 1633.]

  20. Potkin, V. I.; Bumagin, N. A.; Petkevich, S. K.; Lyakhov, A. S.; Rudakov, D. A.; Livantsov, M. V.; Golantsov, N. E. Synthesis 2012, 44, 151.

    Article  CAS  Google Scholar 

  21. Sirko, S. M.; Gorobets, N. Yu.; Musatov, V. I.; Desenko, S. M. Molecules 2009, 14, 5223.

    Article  CAS  Google Scholar 

  22. Ulomskiy, E. N.; El'tsov, O. S.; Borisov, S. S.; Savateev, K. V.; Voinkov, E. K.; Fedotov, V. V.; Rusinov, V. L. Chem. Heterocycl. Compd. 2014, 50, 1005. [Khim. Geterotsikl. Soedin. 2014, 1090.]

  23. Wade, J. J.; Toso, C. B.; Matson, C. J.; Stelzer, V. L. J. Med. Chem. 1983, 26, 608.

    Article  CAS  Google Scholar 

  24. Ulomskii, E. N.; Rusinov, V. L.; Chupakhin, O. N.; Rusinov, G. L.; Chernyshev, A. I.; Aleksandrov, G. G. Chem. Heterocycl. Compd. 1987, 23, 1236. [Khim. Geterotsikl. Soedin. 1987, 1543.]

  25. Mezheritskii, V. V.; Olekhnovich, E. P.; Lukyanov, S. M.; Dorofeenko, G. N. Ortho Esters in Organic Synthesis [in Russian]; Izd-vo Rostov. Un-ta, 1976, p. 95.

  26. http://shelx.uni-ac.gwdg.de/SHELX/download.php

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This work received financial support from the Russian Science Foundation (grants 16-13-00008, 14-13-01301).

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Authors and Affiliations

  1. Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mir St., Yekaterinburg, 620002, Russia

    Victor V. Fedotov, Eugeny N. Ulomskiy, Oleg S. Eltsov, Egor K. Voinkov, Konstantin V. Savateev, Roman A. Drokin, Svetlana K. Kotovskaya & Vladimir L. Rusinov

  2. I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoi / 20 Akademicheskaya St., Yekaterinburg, 620990, Russia

    Evgeny B. Gorbunov

Authors
  1. Victor V. Fedotov
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  2. Eugeny N. Ulomskiy
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  3. Evgeny B. Gorbunov
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  4. Oleg S. Eltsov
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  5. Egor K. Voinkov
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  6. Konstantin V. Savateev
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  7. Roman A. Drokin
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  8. Svetlana K. Kotovskaya
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  9. Vladimir L. Rusinov
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Correspondence to Eugeny N. Ulomskiy.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(5), 582–588

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Fedotov, V.V., Ulomskiy, E.N., Gorbunov, E.B. et al. 3-Nitropyrimido[1,2-a]benzimidazol-4-ones: synthesis and study of alkylation reaction. Chem Heterocycl Comp 53, 582–588 (2017). https://doi.org/10.1007/s10593-017-2095-8

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  • DOI: https://doi.org/10.1007/s10593-017-2095-8

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