Skip to main content
SpringerLink
Log in

Fast and efficient regioselective synthesis of a novel eight membered ring system, 5H-benzo[f]pyrimido[4,5-b][1,5]oxazocine

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

Abstract

An efficient two-steps strategy for the regioselective synthesis of the benzo[f]pyrimido[4,5-b][1,5]oxazocine as a novel tricyclic system has been developed via inter- and intramolecular heterocyclization of 2,4-dichloro-5-(chloromethyl)-6-methylpyrimidine and 2-aminobenzylalcohol in room temperature and short reaction times under mild conditions, followed amination with some secondary amines. 2D-NOESY and HMBC NMR spectroscopy was performed to gain the true regioisomer of the reaction, as well.

Graphic 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

Similar content being viewed by others

References

  1. Qamsari FM, Moradi S, Foroumadi A, Mahdavi M, Moghimi A (2019) Monatsh Chem 150:347

    Article  Google Scholar 

  2. Shigemori H, Kagata T, Ishiyama H, Morah F, Ohsaki A, Kobayashi J (2003) Chem Pharm Bull 51:58

    Article  CAS  Google Scholar 

  3. Zhang CR, Liu HB, Dong SH, Zhu JY, Wu Y, Yue JM (2009) Org Lett 11:4692

    Article  CAS  Google Scholar 

  4. Lounasmaa M, Karvinen E (1993) Heterocycles 36:751

    Article  CAS  Google Scholar 

  5. Jasinski DR, Preston KL (1987) Psychopharmacology 91:273

    Article  CAS  Google Scholar 

  6. Novelli A, Groppetti A, Rossoni G, Manfredi B, Ferrero-Gutiérrez A, Pérez-Gómez A, Desogus C, Fernández-Sánchez M (2007) Amino Acids 32:323

    Article  CAS  Google Scholar 

  7. Seto S, Tanioka A, Ikeda M, Izawa S (2005) Bioorg Med Chem 13:5717

    Article  CAS  Google Scholar 

  8. Seto S, Asano J (2007) Bioorg Med Chem 15:5083

    Article  CAS  Google Scholar 

  9. Seto S, Tanioka A, Ikeda M, Izawa S (2005) Bioorg Med Chem Lett 15:1485

    Article  CAS  Google Scholar 

  10. Araya I, Kanazawa S, Akita H (2008) Chem Pharm Bull 56:176

    Article  CAS  Google Scholar 

  11. Joergensen TK, Andersen KE, Andersen HS, Hohlweg R, Madsen P, Olsen UB (1996) Novel heterocyclic compounds for treatment of pain and/or inflammation. Patent WO 9631497, Oct 10, 1996; (1996) Chem Abstr 126:8146

  12. Ohgoh T, Tanaka S, Fujimoto M, Kitahara A (1977) J Pharm Soc Jpn 97:24

    Article  CAS  Google Scholar 

  13. Gellatly RP, Ollis WD, Sutherland IO (1976) J Chem Soc Perkin Trans 1:913

    Article  Google Scholar 

  14. Tanaka S, Ogata Y (1973) Yakugaku Zasshi 93:1003

    Article  CAS  Google Scholar 

  15. Klohs MW, Draper MD, Petracek FJ, Ginzel KH, Ré ON (1972) Arzneim-Forsch 22:132

    CAS  Google Scholar 

  16. Rao AU, Xiao D, Huang X, Zhou W, Fossetta J, Lundell D, Tian F, Trivedi P, Aslanian R, Palani A (2012) Bioorg Med Chem Lett 22:1068

    Article  CAS  Google Scholar 

  17. Mitra S, Banerjee TS, Hota SK, Bhattacharya D, Das S, Chattopadhyay P (2011) Eur J Med Chem 46:1713

    Article  CAS  Google Scholar 

  18. El-Haddad MN, Elattar KM (2013) Res Chem Intermed 39:3135

    Article  CAS  Google Scholar 

  19. Tanaka S, Hashimoto K, Watanabe H, Sakaguchi K (1973) Chem Pharm Bull 21:1683

    Article  CAS  Google Scholar 

  20. Stillings MR, Freeman S, Myers PL, Readhead MJ, Welbourn AP, Rance MJ, Atkinson DC (1985) J Med Chem 28:225

    Article  CAS  Google Scholar 

  21. Mehrotra KN, Singh IS, Roy J (1985) Bull Chem Soc Jpn 58:2399

    Article  CAS  Google Scholar 

  22. Ouyang X, Kiselyov AS (1999) Tetrahedron Lett 40:5827

    Article  CAS  Google Scholar 

  23. Ouyang X, Kiselyov AS (1999) Tetrahedron 55:8295

    Article  CAS  Google Scholar 

  24. Ouyang X, Chen Z, Liu L, Dominguez C, Kiselyov AS (2000) Tetrahedron 56:2369

    Article  CAS  Google Scholar 

  25. Tang J, Jiang Y-L, Wang B-X, Shen Y-M (2014) Z Naturforsch C: Biosci 69:283

    Article  CAS  Google Scholar 

  26. Shen YM, Yang XL, Chen DQ, Xue J, Zhu L, Fun HK, Hu HW, Xu JH (2010) Chem Eur J 16:2873

    Article  CAS  Google Scholar 

  27. Xue J, Zhu L, Fun H-K, Xu J-H (2000) Tetrahedron Lett 41:8553

    Article  CAS  Google Scholar 

  28. Xiang J, Zhu T, Dang Q, Bai X (2016) Chem Heterocycl Compd 52:601

    Article  CAS  Google Scholar 

  29. Lam H, Qureshi Z, Wegmann M, Lautens M (2018) Angew Chem Int Ed 57:16185

    Article  CAS  Google Scholar 

  30. Xu C, Wang K, Li D, Lin L, Feng X (2019) Angew Chem Int Ed 58:18438

    Article  CAS  Google Scholar 

  31. Sarkar D, Sahoo SR (2019) Eur J Org Chem 2019:2035

    Article  CAS  Google Scholar 

  32. Tsyrenova B, Nenajdenko V (2020) Molecules 25:480

    Article  Google Scholar 

  33. Afrough T, Bakavoli M, Eshghi H, Tajabadi J, Mague J (2019) J Sulfur Chem 40:265

    Article  CAS  Google Scholar 

  34. Karimian A, Eshghi H, Bakavoli M, Shiri A (2017) J Heterocycl Chem 54:151

    Article  CAS  Google Scholar 

  35. Asghari T, Bakavoli M, Rahimizadeh M, Eshghi H, Saberi S, Karimian A, Hadizadeh F, Ghandadi M (2015) Chem Bio Drug Des 85:216

    Article  CAS  Google Scholar 

  36. Batinac S, Sermek DM, Cetina M, Pavelic K, Mintas M, Raic-Malic S (2004) Heterocycles 63:2523

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors are gratefully acknowledged Ferdowsi University of Mashhad for financial support of this project.

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, 91775-1436, Mashhad, Iran

    Toktam Afrough & Hossein Eshghi

Authors
  1. Toktam Afrough
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Hossein Eshghi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Hossein Eshghi.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Afrough, T., Eshghi, H. Fast and efficient regioselective synthesis of a novel eight membered ring system, 5H-benzo[f]pyrimido[4,5-b][1,5]oxazocine. Monatsh Chem 152, 475–479 (2021). https://doi.org/10.1007/s00706-021-02758-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-021-02758-y

Keywords

Search

Navigation