Skip to main content
SpringerLink
Log in

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

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Figure 1
Figure 2
Figure 3

Similar content being viewed by others

References

  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.

  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.

  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.

  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.]

  5. Parfenov, V. E.; Bakharev, V. V.; Zavodskaya, A. V.; Selezneva, E. V.; Gidaspov, A. A.; Suponitsky, K. Yu. Tetrahedron Lett. 2014, 55, 7072.

    Article  CAS  Google Scholar 

  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.hybridised

  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.

  8. Oxford Diffraction (2006). CrysAlis CCD (Version 1.171.29.9) and CrysAlis RED (Version 1.171.29.9). Oxford Diffraction Ltd., Abingdon.

  9. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, 64A, 112.

    Article  Google Scholar 

  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.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Samara State Technical University, 244 Molodogvardeyskaya St., Samara, 443100, Russia

    Vladimir V. Bakharev, Victor E. Parfenov, Alexander A. Gidaspov & Andrey A. Pimenov

  2. I. Ya. Postovsky Institute of Organic Synthesis of the Ural Branch, Russian Academy of Sciencies, 22 S. Kovalevskoi / 20 Akademicheskaya St., Yekaterinburg, 620219, Russia

    Pavel A. Slepukhin

  3. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciencies, 28 Vavilov St, Moscow, 119991, Russia

    Kyrill Yu. Suponitsky

Authors
  1. Vladimir V. Bakharev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Victor E. Parfenov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Alexander A. Gidaspov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Andrey A. Pimenov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Pavel A. Slepukhin
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Kyrill Yu. Suponitsky
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Vladimir V. Bakharev.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(8), 745–748

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Bakharev, V.V., Parfenov, V.E., Gidaspov, A.A. et al. Alkylation of 5-dimethylaminotetrazolo-[1,5-a][1,3,5]triazin-7-one. Chem Heterocycl Comp 51, 745–748 (2015). https://doi.org/10.1007/s10593-015-1768-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-015-1768-4

Keywords

Search

Navigation