Skip to main content
SpringerLink
Log in

Alkylation of [1,2,4]triazolo[1,5-a][1,3,5]triazin-7(3H)-ones

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

The results of pioneering research on the alkylation of fused [1,2,4]triazolo[1,5-a][1,3,5]triazine system are presented, including computational studies of the reaction between 5-dimethylamino[1,2,4]triazolo[1,5-a][1,3,5]triazin-7(3H)-one and bromoethane. The reaction of 5-amino-substituted [1,2,4]triazolo[1,5-a][1,3,5]triazin-7(3H)-ones with allyl bromide, bromoethane, or (2-acetoxyethoxy)methyl bromide occurred selectively with the formation of products due to alkylation at the N-3 nitrogen atom of the heterocyclic system. The removal of acetyl protecting group from 5-amino-substituted {2-[(7-oxo[1,2,4]triazolo[1,5-a][1,3,5]triazin-3(7H)-yl)methoxy]ethyl}acetates gave 5-aza analogs of acyclovir, containing a substituted amino group at position 5 of the heterocyclic 3-[(2-hydroxyethoxy)methyl][1,2,4]-triazolo[1,5-a][1,3,5]triazin-7(3H)-one system.

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
Scheme 4
Figure 2

Similar content being viewed by others

References

  1. Sari, O.; Roy, V.; Agrofoglio, L. A. In Chemical Synthesis of Nucleoside Analogues; Merino, P., Ed.; John Wiley & Sons, Inc.: Hoboken, 2013, p. 49.

  2. Guo, H.-M.; Wu, S.; Niu, H.-Y.; Song, G.; Qu, G.-R. In Chemical Synthesis of Nucleoside Analogues; Merino, P., Ed.; John Wiley & Sons, Inc.: Hoboken, 2013, p. 103.

  3. (a) Saito, A.; Shimizu, B. Bull. Chem. Soc. Jpn. 1977, 50, 1596. (b) 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. (c) Astakhov, A. V.; Sokolov, A. N.; Pyatakov, D. A.; Shishkina, S. V.; Shishkin, O. V.; Chernyshev, V. M. Chem. Heterocycl. Compd. 2015, 51, 1039. [Khim. Geterotsikl. Soedin. 2015, 51, 1039.] (d) Rusinov, V. L.; Ulomskii, E. N.; Chupakhin, O. N.; Charushin, V. N. Russ. Chem. Bull., Int. Ed. 2008, 57, 985 [Izv. Akad. Nauk, Ser. Khim. 2008, 967.]

  4. (a) Peng, H.; Kumaravel, G.; Yao, G.; Sha, L.; Wang, J.; Van Vlijmen, H.; Bohnert, T.; Huang, C.; Vu, C. B.; Ensinger, C. L.; Chang, H.; Engber, T. M.; Whalley, E. T.; Petter, R. C. J. Med. Chem. 2004, 47, 6218. (b) Vu, C. B.; Pan, D.; Peng, B.; Kumaravel, G.; Smits, G.; Jin, X.; Phadke, D.; Engber, T.; Huang, C.; Reilly, J.; Tam, S.; Grant, D.; Hetu, G.; Petter, R. C. J. Med. Chem. 2005, 48, 2009. (c) Vu, C. B.; Peng, B.; Kumaravel, G.; Smits, G.; Jin, X.; Phadke, D.; Engber, T.; Huang, C.; Reilly, J.; Tam, S.; Grant, D.; Hetu, G.; Chen, L.; Zhang, J.; Petter, R. C. J. Med. Chem. 2004, 47, 4291. (d) Vu, C. B.; Shields, P.; Peng, B.; Kumaravel, G.; Jin, X.; Phadke, D.; Wang, J.; Engber, T.; Ayyub, E.; Petter, R. C. Bioorg. Med. Chem. Lett. 2004, 14, 4835. (e) de Zwart, M.; Vollinga, R. C.; Beukers, M. W.; Sleegers, D. F.; von Frijtag Drabbe Künzel, J. K.; de Groote, M.; Ijzerman, A. P. Drug Dev. Res. 1999, 48, 95.

  5. Akahoshi, F.; Okada, T.; Takeda, S.; Naito, Y.; Fukaya, C.; Kuwahara, S.; Kajii, M.; Nishimura, H.; Suguira, M. WO Patent 9503286.

  6. Suzuki, F.; Koike, N.; Shimada, J.; Kitamura, S.; Ichikawa, S.; Nakamura, J.; Shiozaki, S. WO Patent 9507282.

  7. (a) Bekircan, O.; Küxük, M.; Kahveci, B.; Kolaylı, S. Arch. Pharm. 2005, 338, 365. (b) Langdon, S. P.; Simmonds, R. J.; Stevens, M. F. G. J. Chem. Soc., Perkin Trans. 1 1984, 993.

  8. (a) Cartwright, D.; Urlwin-Smith, P. L. US Patent 4133674. (b) Gesing, E.; Santel, H.-J.; Luerssen, K.; Schmidt, R. R. DE Patent 4106100. (c) Pearson, N.; Kleschick, W. US Patent 4605433. (d) Pearson, N.; Kleschick, W. US Patent 4685958. (e) Westermann, J.; Kruger, M.; Arndt, F.; Rees, R.; Koetter, C. DE Patent 3644343.

  9. Kaiser, D. W.; Peters, G. A.; Wystrach, V. P. J. Org. Chem. 1953, 18, 1610.

    Article  CAS  Google Scholar 

  10. Bakharev, V. V.; Parfenov, V. E.; Ul'yankina, I. V.; Zavodskaya, A. V.; Selezneva, E. V.; Gidaspov, A. A.; Eltsov, O. S.; Slepukhin, P. A. Tetrahedron 2014, 70, 6825.

    Article  CAS  Google Scholar 

  11. Bakharev, V. V.; Parfenov, V. E.; Gidaspov, A. A.; Pimenov, A. A.; Slepukhin, P. A.; Suponitsky, K. Yu. Chem. Heterocycl. Compd. 2015, 51, 745. [Khim. Geterotsikl. Soedin. 2015, 51, 745.]

  12. Lieber, E.; Rao, C. N. R.; Chao, T. S.; Rubinstein, H. Can. J. Chem. 1958, 36, 1441.

    Article  CAS  Google Scholar 

  13. Shastin, A. V.; Godovikova, T. I.; Golova, S. P.; Povorin, M. V.; Dmitriev, D. E.; Dekaprilevich, M. O.; Strelenko, Y. A.; Struchkov, Y. T.; Khmel'nitskii, L. I.; Korsunskii, B. L. Chem. Heterocycl. Compd. 1995, 31, 601. [Khim. Geterotsikl. Soedin. 1995, 679.]

  14. 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, Revision A.1, Gaussian, Inc.: Wallingford, 2009.

Download references

The work was performed with financial support from the Ministry of Education and Science of the Russian Federation within the framework of the Project part of State Assignment to the Samara State Technical University (project No. 4.813.2014/K).

Author information

Authors and Affiliations

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

    Irina V. Ul′yankina, Anna V. Zavodskaya, Victor E. Parfenov, Alexander A. Gidaspov, Andrey K. Shiryaev, Eugenia V. Selezneva & Vladimir V. Bakharev

Authors
  1. Irina V. Ul′yankina
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Anna V. Zavodskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Victor E. Parfenov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Alexander A. Gidaspov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Andrey K. Shiryaev
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Eugenia V. Selezneva
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Vladimir V. Bakharev
    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, 2016, 52(12), 1054–1060

Electronic supplementary material

Below is the link to the electronic supplementary material.

ESM 1

(PDF 5194 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ul′yankina, I.V., Zavodskaya, A.V., Parfenov, V.E. et al. Alkylation of [1,2,4]triazolo[1,5-a][1,3,5]triazin-7(3H)-ones. Chem Heterocycl Comp 52, 1054–1060 (2016). https://doi.org/10.1007/s10593-017-2006-z

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-017-2006-z

Keywords

Search

Navigation