Skip to main content
SpringerLink
Log in

Synthesis of benzooxadiazocines via the acid-catalyzed reaction of pyrimidine-containing acetals with resorcinol derivatives

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

Herein, we report the synthesis of heteroannelated benzooxadiazocines via unusual reaction of pyrimidine-containing acetal with resorcinol derivatives.

Graphical abstract

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

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

References

  1. Kappe CO (2000) Eur J Med Chem 35:1043

    Article  CAS  Google Scholar 

  2. Kappe CO (1999) Synthesis 1999:1799

    Article  Google Scholar 

  3. Grover GJ, Dzwonczyk S, McMullen DM, Normandin DE, Parham CS, Sleph PG, Moreland S (1995) J Cardiovasc Pharmacol 26:289

    Article  CAS  Google Scholar 

  4. Mayer TU (1999) Science 286:971

    Article  CAS  Google Scholar 

  5. Kapoor TM, Mayer TU, Coughlin ML, Mitchison TJ (2000) J Cell Biol 150:975

    Article  CAS  Google Scholar 

  6. Wood K (2001) Curr Opin Pharmacol 1:370

    Article  CAS  Google Scholar 

  7. Wood WK, Bergnes G (2004) Annu Rep Med Chem 39:173

    Article  CAS  Google Scholar 

  8. Sarli V, Huemmer S, Sunder-Plassmann N, Mayer TU, Giannis A (2005) ChemBioChem 6:2005

    Article  CAS  Google Scholar 

  9. Gartner M, Sunder-Plassmann N, Seiler J, Utz M, Vernos I, Surrey T, Giannis A (2005) ChemBioChem 6:1173

    Article  CAS  Google Scholar 

  10. Yar M, Bajda M, Shahzadi L, Shahzad SA, Ahmed M, Ashraf M, Alam U, Khan IU, Khan AF (2014) Bioorg Chem 54:96

    Article  CAS  Google Scholar 

  11. Jing X, Li Z, Pan X, Wang Q, Yan C, Zhu H (2009) Synth Commun 39:3796

    Article  CAS  Google Scholar 

  12. Mobinikhaledi A, Foroughifar N, Mosleh T, Hamta A (2012) Phosphorus. Sulfur Silicon Relat Elem 187:728

    Article  CAS  Google Scholar 

  13. Liu Q, Xu J, Teng F, Chen A, Pan N, Zhang W (2014) J Heterocycl Chem 51:741

    Article  CAS  Google Scholar 

  14. Svetlik J, Hanus V, Bella J (1991) J Chem Res (S) 1:4

    Google Scholar 

  15. Svetlik J, Veizerova L, Liptaj T, Kubist J (2009) Arkivoc 2009:79

    Article  Google Scholar 

  16. Finkelstein BL, Benner EA, Hendrixson MC, Kranis KT, Rauh JJ, Sethuraman MR, McCann SF (2002) Bioorg Med Chem 10:599

    Article  CAS  Google Scholar 

  17. Cheng Q, Wang Q, Tan T, Chen N, Shuai M (2012) J Heterocycl Chem 49:1352

    Article  CAS  Google Scholar 

  18. Cheng Q, Wang Q, Xu X, Ruan M, Yao H, Yang X (2010) J Heterocycl Chem 47:624

    Article  CAS  Google Scholar 

  19. Svetlik J, Tureeek F, Hanus V (1988) J Chem Soc Perkin Trans 1:2053

    Article  Google Scholar 

  20. Svetlik J, Veizerová L, Mayer TU, Catarinella M (2010) Bioorg Med Chem Lett 20:4073

    Article  CAS  Google Scholar 

  21. Bartashevich EV, Plekhanov PV, Rusinov GL, Potemkin VA, Belik AV, Chupakhin ON (1999) Russ Chem Bull Int Ed 48:1553

    Article  CAS  Google Scholar 

  22. Verbitskiy EV, Kvashnin YA, Slepukhin PA, Kuchin AV, Rusinov GL, Chupakhin ON, Charushina VN (2011) Russ Chem Bull Int Ed 60:919

    Article  CAS  Google Scholar 

  23. Svetlik J, Liptaj T, Turecek F (1999) J Heterocycl Chem 36:209

    Article  CAS  Google Scholar 

  24. Fu N-Y, Yuan Y-F, Cao Z, Wang S-W, Wang J-T, Peppe C (2002) Tetrahedron 58:4801

    Article  CAS  Google Scholar 

  25. Svetlik J, Veizerova L, Kettmann V (2008) Tetrahedron Lett 49:3520

    Article  CAS  Google Scholar 

  26. Bartashevich EV, Potemkin VA, Beresnev DG, Rusinov GL, Chupakhin ON (2003) Russ J Gen Chem 73:816

    Article  CAS  Google Scholar 

  27. Gazizov AS, Kharitonova NI, Burilov AR, Pudovik MA, Sinyashin OG (2013) Monatsh Chem 144:1027

    Article  CAS  Google Scholar 

  28. Gazizov AS, Kharitonova NI, Smolobochkin AV, Syakaev VV, Burilov AR, Pudovik MA (2015) Monatsh Chem 146:1845

    Article  CAS  Google Scholar 

  29. Cremer D, Pople JA (1975) J Am Chem Soc 97:1354

    Article  CAS  Google Scholar 

  30. Karplus M (1963) J Am Chem Soc 85:2870

    Article  CAS  Google Scholar 

  31. Sedova VF, Krivopalov VP, Gatilov YV, Shkurko OP (2014) Russ Chem Bull Int Ed 63:1378

    Article  CAS  Google Scholar 

  32. Weis AL, Frolow F (1984) J Org Chem 49:3635

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by the Russian Scientific Foundation (Grant No. 14-50-00014).

Author information

Authors and Affiliations

  1. A.E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, Arbuzov Str. 8, Kazan, Russian Federation, 420088

    Almir S. Gazizov, Natalya I. Kharitonova, Victor V. Syakaev, Alexey B. Dobrynin, Alexander R. Burilov & Michail A. Pudovik

Authors
  1. Almir S. Gazizov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Natalya I. Kharitonova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Victor V. Syakaev
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Alexey B. Dobrynin
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Alexander R. Burilov
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Michail A. Pudovik
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Almir S. Gazizov.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (PDF 1341 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Gazizov, A.S., Kharitonova, N.I., Syakaev, V.V. et al. Synthesis of benzooxadiazocines via the acid-catalyzed reaction of pyrimidine-containing acetals with resorcinol derivatives. Monatsh Chem 147, 2113–2117 (2016). https://doi.org/10.1007/s00706-016-1840-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-016-1840-5

Keywords

Search

Navigation