Skip to main content
SpringerLink
Log in

A simple and regioselective one-pot procedure for the direct N-acylation of some purine and pyrimidine nucleobases via carboxylic acids using cyanuric chloride

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

Abstract

A facile and selective one-pot N-acylation of nucleobases via carboxylic acids using cyanuric chloride (2,4,6-trichloro-1,3,5-triazine) is described. In this protocol, the reaction of diverse carboxylic acids with pyrimidine and/or purine nucleobases is efficiently achieved in the presence of cyanuric chloride and NaH/Et3N in DMF/MeCN (1:1, v/v) to afford the corresponding N-acyl nucleobases in good yields.

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.

Similar content being viewed by others

References

  1. Kleeman A, Engel J, Kutscher B, Reichert D (1999) Pharmaceutical substances, 3rd edn. Thieme, Stuttgart

    Google Scholar 

  2. De Clercq E (1993) In: Johnsson NG (ed) Advances in antiviral drug design, vol 1. JAI Press, Greenwich, p 88

    Google Scholar 

  3. Pathak T (2002) Chem Rev 102:1623

    Article  CAS  Google Scholar 

  4. Agrofoglio LA, Gillaizeau I, Saito Y (2003) Chem Rev 103:1875

    Article  CAS  Google Scholar 

  5. Huryn DM, Okabe M (1992) Chem Rev 92:1745

    Article  CAS  Google Scholar 

  6. Khalafi-Nezhad A, Soltani Rad MN, Moosavi-Movahedi AA, Kosari M (2007) Helv Chim Acta 90:730

    Article  CAS  Google Scholar 

  7. Khalafi-Nezhad A, Soltani Rad, MN, Khoshnood A (2004) Synthesis 583

  8. Khalafi-Nezhad A, Zarea A, Soltani Rad MN, Mokhtari B Parhami A (2005) Synthesis 419

  9. Choi JR, Cho DG, Roh KY, Hwang JT, Ahn S, Jang HS, Cho WY, Kim KW, Cho YG, Kim J, Kim YZ (2004) J Med Chem 47:2864

    Article  CAS  Google Scholar 

  10. Amblard F, Nolan SP, Schinazi RF, Agrofoglio LA (2005) Tetrahedron 61:537

    Article  CAS  Google Scholar 

  11. Bryant JD, Keyser GE, Barrio JR (1979) J Org Chem 44:3733

    Article  CAS  Google Scholar 

  12. Herdewijn P (2008) Modified nucleosides. In: Biochemistry, biotechnology and medicine. Wiley-VCH, Weinheim

  13. Chu CK (2002) Recent advances in nucleosides: chemistry and chemotherapy. Elsevier Science, Amsterdam

    Google Scholar 

  14. Romeo G, Chiacchio U, Corsaro A, Merino P (2010) Chem Rev 110:3337

    Article  CAS  Google Scholar 

  15. Mieczkowski A, Roy V, Agrofoglio LA (2010) Chem Rev 110:1828

    Article  CAS  Google Scholar 

  16. Cruickshank KA, Jiricny J, Reese CB (1984) Tetrahedron Lett 25:681

    Article  CAS  Google Scholar 

  17. Ti GS, Gaffney BL, Jones RA (1982) J Am Chem Soc 104:1316

    Article  CAS  Google Scholar 

  18. Zhu XF, Williams HJ, Scott AI (2003) Synth Commun 33:1233

    Article  CAS  Google Scholar 

  19. Zhang ZL, Han P, Ma XY, Liu J, Wang XW, Liu JY (2005) Chin Chem Lett 16:287

    CAS  Google Scholar 

  20. Nováček A, Hesoun D, Gut J (1965) Collect Czech Chem Commun 30:1890

    Article  Google Scholar 

  21. Spector LB, Keller EB (1958) J Biol Chem 232:185

    CAS  Google Scholar 

  22. Bhat V, Ugarkar BG, Sayeed VA, Grimm K, Kosora N, Domenico PA, Stocker E (1989) Nucleosides Nucleotides 8:179

    Article  CAS  Google Scholar 

  23. Kumar A, Singh D, Wani MJ, Joshi NS, Thombre PS, Rawat AS (2000) Process for preparation of acyclic nucleosides. (1997) Chem Abstr 127:346617. US Patent 6,043,364, March 28 2000

  24. Blotny G (2006) Tetrahedron 62:9507 and references cited therein

  25. Soltani Rad MN, Behrouz S (2011) Synlett 2562

  26. Soltani Rad MN, Khalafi-Nezhad A, Asrari Z, Behrouz S, Amini Z, Behrouz M (2009) Synthesis 3983

  27. Soltani Rad MN, Khalafi-Nezhad A, Asrari Z, Behrouz S (2010) Synthesis 2599

  28. Soltani Rad MN, Khalafi-Nezhad A, Behrouz S (2009) Helv Chim Acta 92:1760

  29. Soltani Rad MN, Khalafi-Nezhad A, Behrouz S (2010) Beilstein J Org Chem 6:49

  30. Soltani Rad MN, Khalafi-Nezhad A, Behrouz S, Faghihi MA, Zare A, Parhami A (2008) Tetrahedron 64:1778

  31. Soltani Rad MN, Khalafi-Nezhad A, Behrouz S, Asrari Z, Behrouz M, Amini Z (2009) Synthesis 3067

  32. Soltani Rad MN, Behrouz S, Doroodmand MM, Moghtaderi N (2011) Synthesis 3915

  33. Soltani Rad MN, Khalafi-Nezhad A, Divar M, Behrouz S (2010) Phosphorus. Sulfur Silicon Relat Elem 185:1943

    Article  Google Scholar 

  34. Venkataraman K, Wagle DR (1979) Tetrahedron Lett 20:3037

    Article  Google Scholar 

  35. Bandgar BP, Pandit SS (2002) Tetrahedron Lett 43:3413

    Article  CAS  Google Scholar 

  36. Kaminski ZJ, Paneth P, Rudzinski J (1998) J Org Chem 63:4248

    Article  CAS  Google Scholar 

  37. Rayle HL, Fellmeth L (1999) Org Process Res Dev 3:172

    Article  CAS  Google Scholar 

  38. Gambacorta’ A, Farah ME, Tofani D (1999) Tetrahedron Lett 55:12615

    Article  Google Scholar 

  39. Pal A, Salandria KJ, Arico JW, Schlegel MK, McLaughlin LW (2013) Chem Commun 49:2936

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We wish to thank the Shiraz University of Technology and Shiraz University Research Councils for partial support of this work.

Author information

Authors and Affiliations

  1. Department of Chemistry, Shiraz University of Technology, 71555-313, Shiraz, Iran

    Mohammad Navid Soltani Rad & Somayeh Behrouz

  2. Department of Chemistry, College of Sciences, Shiraz University, 71454, Shiraz, Iran

    Zeinab Asrari & Ali Khalafi-Nezhad

Authors
  1. Mohammad Navid Soltani Rad
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Somayeh Behrouz
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Zeinab Asrari
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Ali Khalafi-Nezhad
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Mohammad Navid Soltani Rad or Somayeh Behrouz.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (PDF 1339 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Soltani Rad, M.N., Behrouz, S., Asrari, Z. et al. A simple and regioselective one-pot procedure for the direct N-acylation of some purine and pyrimidine nucleobases via carboxylic acids using cyanuric chloride. Monatsh Chem 145, 1933–1940 (2014). https://doi.org/10.1007/s00706-014-1270-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-014-1270-1

Keywords

Search

Navigation