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Chemistry of Heterocyclic Compounds

, Volume 51, Issue 8, pp 745–748 | Cite as

Alkylation of 5-dimethylaminotetrazolo-[1,5-a][1,3,5]triazin-7-one

  • Vladimir V. Bakharev
  • Victor E. Parfenov
  • Alexander A. Gidaspov
  • Andrey A. Pimenov
  • Pavel A. Slepukhin
  • Kyrill Yu. Suponitsky
Article
Reaction of 5-dimethylaminotetrazolo[1,5-а][1,3,5]triazin-7-one tetrabutylammonium salt with allyl bromide in acetonitrile proceeds with the formation of 3-allyl-5-dimethylaminotetrazolo[1,5-a][1,3,5]triazin-7-one (N-alkylation), 6-allyloxy-4-azido-N,N-dimethyl-1,3,5-triazin-2-amine (O-alkylation), and 2-(1-allyl-1H-tetrazol-5-yl)-1,1-dimethylguanidine as the product of hydrolysis of N-alkylated tetrazolo[1,5-a][1,3,5]triazin-7-one. The structure of the reaction products was confirmed by IR, 1H and 13C NMR spectroscopy as well as elemental and X-ray structural analysis data.

Keywords

tetrazolo[1,5-a][1,3,5]triazines alkylation ambident nucleophiles anomalous nucleosides tetrazolylguanidines 

References

  1. 1.
    (a) De Clercq, E. Nucleosides, Nucleotides Nucleic Acids 2012, 31, 339. (b) Ojwang, J. O.; Ali, S.; Smee, D. F.; Morrey, J. D.; Shimasaki, C. D.; Sidwell, R. W. Antiviral Res. 2005, 68, 49. (c) Krečmerová, M.; Otmar, M. Future Med. Chem. 2012, 4, 991.Google Scholar
  2. 2.
    Guo, H.-M.; Wu, S.; Niu, H.-Y.; Song, G.; Qu, G.-R. In Chemical Synthesis of Nucleoside Analogues; John Wiley & Sons, Inc., 2013, p. 103.Google Scholar
  3. 3.
    (a) Khalymbadzha, I. A.; Shestakova, T. S.; Subbotina, J. O.; Eltsov, O. S.; Musikhina, A. A.; Rusinov, V. L.; Chupakhin, O. N.; Karpenko, I. L.; Jasko, M. V.; Kukhanova, M. K.; Deev, S. L. Tetrahedron 2014, 70, 1298. (b) Kjellberg, J.; Johansson, N. G. Nucleosides Nucleotides 1989, 8, 225.Google Scholar
  4. 4.
    (a) Bakharev, V. V.; Gidaspov, A. A. Chem. Heterocycl. Compd. 2006, 42, 417. [Khim. Geterotsikl. Soedin. 2006, 466.] (b) Fedorov, B. S.; Utienyshev, A. N.; Ghidaspov, A. A.; Kachanovskaya, E. V.; Bakharev, V. V.; Fadeev, M. A. Chem. Heterocycl. Compd. 2005, 41, 496. [Khim. Geterotsikl. Soedin. 2005, 582.]Google Scholar
  5. 5.
    Parfenov, V. E.; Bakharev, V. V.; Zavodskaya, A. V.; Selezneva, E. V.; Gidaspov, A. A.; Suponitsky, K. Yu. Tetrahedron Lett. 2014, 55, 7072.CrossRefGoogle Scholar
  6. 6.
    (a) Golankiewicz, B.; Januszczyk, P.; Zeidler, J.; Popenda, M. Nucleosides Nucleotides Nucleic Acids 2004, 23, 127. (b) Gelotte, K. O.; Mason, D. N.; Meckler, H.; Shieh, W.-C.; Starkey, C. M. J. Heterocycl. Chem. 1990, 27, 1549. (c) Francis, J. E.; Cash, W. D.; Psychoyos, S.; Ghai, G.; Wenk, P.; Friedmann, R. C.; Atkins, C.; Warren, V.; Furness, P.; Hyun, J. L.; Stone, G. A.; Desai, M.; Williams, M. J. Med. Chem. 1988, 31, 1014. (d) Rusinov, V. L.; Ulomskii, E. N.; Kozhevnikov, D. N.; Chupakhin, O. N.; Aleksandrov, G. G. Zh. Org. Khim. 1996, 32, 770. (e) Rusinov, V. L.; Ulomskii, E. N.; Aleksandrov, G. G.; Parshin, V. E.; Chupakhin, O. N. Chem. Heterocycl. Compd. 1991, 27, 561. [Khim. Geterotsikl. Soedin. 1991, 700.] (f) Orihuela, S.; Sánchez, M. P. ; Quirós, M.; Molina, J.; Faure, R. J. Mol. Struct. 1997, 415, 285. (g) Schroeter, G.; Finck, E. Ber. Dtsch. Chem. Ges. 1938, 71, 671.hybridisedGoogle Scholar
  7. 7.
    (a) Moriarty, R. M.; Bailey III, B. R.; Prakash, I.; Miller, R. S. J. Org. Chem. 1985, 50, 3710. (b) Peet, N. P. J. Heterocycl. Chem. 1987, 24, 223.Google Scholar
  8. 8.
    Oxford Diffraction (2006). CrysAlis CCD (Version 1.171.29.9) and CrysAlis RED (Version 1.171.29.9). Oxford Diffraction Ltd., Abingdon.Google Scholar
  9. 9.
    Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, 64A, 112.CrossRefGoogle Scholar
  10. 10.
    Macrae, C. F.; Bruno, I. J.; Chisholm, J. A.; Edgington, P. R.; McCabe, P.; Pidcock, E.; Rodriguez-Monge, L.; Taylor, R.; van de Streek, J.; Wood, P. A. J. Appl. Crystallogr. 2008, 41, 466.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2015

Authors and Affiliations

  • Vladimir V. Bakharev
    • 1
  • Victor E. Parfenov
    • 1
  • Alexander A. Gidaspov
    • 1
  • Andrey A. Pimenov
    • 1
  • Pavel A. Slepukhin
    • 2
  • Kyrill Yu. Suponitsky
    • 3
  1. 1.Samara State Technical UniversitySamaraRussia
  2. 2.I. Ya. Postovsky Institute of Organic Synthesis of the Ural BranchRussian Academy of ScienciesYekaterinburgRussia
  3. 3.A. N. Nesmeyanov Institute of Organoelement CompoundsRussian Academy of ScienciesMoscowRussia

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