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7-Alkylamino-6-nitrotetrazolo[1,5-a]pyrimidines as precursors of anomalous nucleosides and heterocycles with potential antiseptic activity

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Chemistry of Heterocyclic Compounds Aims and scope

A method was developed for the synthesis of 7-alkylamino-5-methyl-6-nitrotetrazolo[1,5-a]pyrimidines from the readily available 5-methyl-6-nitrotetrazolo[1,5-a]pyrimidin-7(4H)-one by using a sequence of chlorodeoxygenation and amination reactions. The chlorinated intermediate formed along this route was isolated and characterized as 7-chloro-5-methyl-6-nitrotetrazolo[1,5-a]pyrimidine.

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References

  1. Mathé, C.; Lioux, T.; Gosselin, G. Nucleosides, Nucleotides Nucleic Acids 2003, 22, 605.

    Article  Google Scholar 

  2. Zheng, Z.; Tran, H.-A.; Manivannan, S.; Wen, X.; Kaiser, M.; Brun, R.; Snyder, F. F.; Back, T. G. Bioorg. Med. Chem. Lett. 2016, 12, 2861.

    Article  Google Scholar 

  3. Lioux, T.; Gosselin, G.; Mathé, C. Eur. J. Org. Chem. 2003, 3997.

  4. Cosyn, L.; Palaniappan, K. K.; Kim, S.-K.; Duong, H. T.; Gao, Z.-G.; Jacobson, K. A.; Van Calenbergh, S. J. Med. Chem. 2006, 49, 7373.

  5. Sarvary, А.; Maleki, A. Mol. Diversity 2015, 19, 189.

    Article  CAS  Google Scholar 

  6. Dolzhenko, A. V. Heterocycles 2017 , 94, 1819.

    Article  CAS  Google Scholar 

  7. Sirakanyan, S. N.; Spinelli, D.; Geronikaki, A.; Hovakimyan, A. A.; Noravyan, A. S. Tetrahedron 2014, 70, 8648.

    Article  CAS  Google Scholar 

  8. Deev, S. L.; Shenkarev, Z. O.; Shestakova, T. S.; Chupakhin, O. N.; Rusinov, V. L.; Arseniev, A. S. J. Org. Chem. 2010, 75, 8487.

    Article  CAS  Google Scholar 

  9. Kvaskoff, D.; Bednarek, P.; George, L.; Waich, K.; Wentrup, C. J. Org. Chem. 2006, 71, 4049.

    Article  CAS  Google Scholar 

  10. Khalymbadzha, I. A.; Shestakova, T. S.; Deev, S. L.; Rusinov, V. L.; Chupakhin, O. N.; Shenkarev, Z. O.; Arseniev, A. S. Russ. Chem. Bull., Int. Ed. 2013, 62, 521. [Izv. Akad. Nauk, Ser. Khim. 2013, 519.]

  11. Shestakova, T. S.; Shenkarev, Z. O.; Deev, S. L.; Chupakhin, O. N.; Khalymbadzha, I. A.; Rusinov, V. L.; Arseniev, A. S. J. Org. Chem. 2013, 78, 6975.

    Article  CAS  Google Scholar 

  12. Takeuchi, H.; Watanabe, K. J. Phys. Org. Chem. 1998, 11, 478.

    Article  CAS  Google Scholar 

  13. Savateev, K. V.; Ulomsky, E. N.; Fedotov, V. V.; Rusinov, V. L.; Sivak, K. V.; Lyubishin, M. M.; Kuzmich, N. N.; Aleksandrov, A. G. Russ. J. Bioorg. Chem. 2017, 43, 421. [Bioorgan. Khim. 2017, 43, 402.]

  14. Poucher, S. M.; Keddie, J. R.; Singh, P.; Stoggall, S. M.; Caulkett, P. W.; Jones, G.; Coll, M. G. Br. J. Pharmacol. 1995, 115, 1096.

    Article  CAS  Google Scholar 

  15. Sivak, K. V.; Vasin, A. V.; Egorov, V. V.; Tsvetkov, V. B.; Kuz'mich, N. N.; Savina, V. A.; Kiselev, O. I. Mol. Biologiya 2016, 50, 231.

    CAS  Google Scholar 

  16. Chupakhin, O. N.; Rusinov, V. L.; Ulomskiy, E. N.; Charushin, V. N.; Petrov, A. Yu.; Kiselev, O. I. RU patent 2294936.

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

  18. Wiley, R. H.; Lanet, J.; Hussung, K. H. J. Heterocycl. Chem. 1964, 1, 175.

    Article  CAS  Google Scholar 

  19. Rusinov, V. L.; Chupakhin, O. N. Nitroazines [in Russian]; Vlasov, V. M., Ed.; Nauka: Novosibirsk, 1991.

    Google Scholar 

  20. Romanova, I. P.; Kalinin, V. V.; Nafikova, A. A.; Yakhvarov, D. G.; Zverev, V. V.; Kovalenko, V. I.; Rusinov, G. L.; Plekhanov, P. V.; Charushin, V. N.; Sinyashina, O. G. Russ. Chem. Bull., Int. Ed. 2003, 52, 173. [Izv. Akad. Nauk, Ser. Khim. 2003, 163.]

  21. Romanova, I. P.; Kalinin, V. V.; Yakhvarov, D. G.; Nafikova, A. A.; Kovalenko, V. I.; Plekhanov, P. V.; Rusinov, G. L.; Sinyashin, O. G. Mendeleev Commun. 2002, 12, 51.

    Article  Google Scholar 

  22. Brady, L. E.; Herbst, R. M. J. Org. Chem. 1959, 24, 922.

    Article  CAS  Google Scholar 

  23. Kato, T.; Chiba, T.; Daneshtalab, M. Chem. Pharm. Bull. 1976, 24, 2549.

    Article  CAS  Google Scholar 

  24. Kofman, T. P.; Uvarova, T. A.; Kartseva, G. Y.; Uspenskaya, T. L. Russ. J. Org. Chem. 1997, 33, 1784. [Zh. Org. Khim. 1997, 33, 1867.]

  25. Savateev, K. V.; Ulomsky, E. N.; Rusinov, V. L.; Isenov, M. L.; Chupakhin, O. N. Russ. Chem. Bull., Int. Ed. 2015, 64, 1378. [Izv. Akad. Nauk, Ser. Khim. 2015, 1378.]

  26. Savateev, K. V.; Ulomsky, E. N.; Borisov, S. S.; Voinkov, E. K.; Fedotov, V. V.; Rusinov, V. L. Chem. Heterocycl. Compd. 2014, 50, 880. [Khim. Geterotsikl. Soedin. 2014, 953.]

  27. Nitrogen NMR; Witanowski, M.; Webb, G. A., Eds.; Plenum Press: London, 1973, p. 210.

  28. Sharp, J. T.; Gosney, I.; Rowley, A. G. Practical Organic Chemistry; Chapman and Hall Ltd.: London, 1989, p. 160.

    Book  Google Scholar 

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This work received financial support from the Russian Foundation for Basic Research (grant 16-33-00159 mol_a).

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Correspondence to Konstantin V. Savateev.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(2), 197–204

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Savateev, K.V., Fedotov, V.V., Ulomskiy, E.N. et al. 7-Alkylamino-6-nitrotetrazolo[1,5-a]pyrimidines as precursors of anomalous nucleosides and heterocycles with potential antiseptic activity. Chem Heterocycl Comp 54, 197–204 (2018). https://doi.org/10.1007/s10593-018-2254-6

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  • DOI: https://doi.org/10.1007/s10593-018-2254-6

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