Skip to main content
SpringerLink
Log in

Pd-catalyzed coupling reaction of 6-hydroxy-2-(prop-2-yn-1-ylsulfanyl)pyrimidin-4(1H)-one with aryl iodides: efficient syntheses of new 3-benzylthiazolo[3,2-a]pyrimidinones

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

An efficient synthetic protocol was developed for the preparation of 3-benzyl-7(5)-hydroxy-5(7)H-[1,3]thiazolo[3,2-a]pyrimidin-5(7)-ones from 6-hydroxy-2-(prop-2-yn-1-ylsulfanyl)pyrimidin-4(1H)-one and aryl iodides in the presence of Pd–Cu complex catalyst. This one-pot process provides a simple and direct method for the synthesis of new thiazolo[3,2-a]pyrimidinones in good to high yields.

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

Similar content being viewed by others

References

  1. Ozair, A.; Suroor, A. K.; Nadeem, S.; Waquar, A. Med. Chem. Res. 2010, 19, 1245.

    Article  Google Scholar 

  2. Kappe, C. O.; Fabian, W. M. F.; Semones, M. A. Tetrahedron 1997, 53, 2803.

    Article  CAS  Google Scholar 

  3. Atwal, K. S.; Swanson, B. N.; Unger, S. E.; Floyd, D. M.; Moreland, S.; Hedberg, A.; O'Reilly, B. C. J. Med. Chem. 1991, 34, 806.

    Article  CAS  Google Scholar 

  4. Shiryaev, A. K.; Baranovskaya, N. S.; Eremin, M. S. Chem. Heterocycl. Compd. 2013, 48, 1550. [Khim. Geterotsikl. Soedin. 2012, 1662.]

  5. Singh, S.; Schober, A.; Michael, G.; Alexander, G. G. Tetrahedron 2011, 52, 3814.

    Article  CAS  Google Scholar 

  6. Kulakov, I. V.; Nurkenov, O. A.; Turdybekov, D. M.; Issabaeva, G. M.; Mahmutova, A. S.; Turdybekov, K. M. Chem. Heterocycl. Compd. 2009, 45, 856. [Khim. Geterotsikl. Soedin. 2009, 1075.]

  7. Geist, J. G.; Lauw, S.; Illarinova, V.; Fischer, M.; Gwawert, T.; Rohdich, F.; Eisenreich, W.; Kaiser, J.; Groll, M.; Scheurer, C. ChemMedChem 2010, 5, 1092.

    Article  CAS  Google Scholar 

  8. Amr, A. E. G.; Maigali, S. S.; Abdulla, M. M. Monatsh. Chem. 2008, 139, 1409.

    Article  CAS  Google Scholar 

  9. Branstetter, B. J.; Breitenbucher, J. G.; Lebsack, A. D.; Xiao, W. Patent WO2008005303.

  10. Flefel, E. E.; Salama, M. A.; El-Shahat, M.; El-Hashash, M. A.; El-Farargy, A. F. Phosphorus, Sulfur Silicon Relat. Elem. 2007, 182, 1739.

  11. Hammam, A. G.; Sharaf, M. A.; Abdel Hafez, N. A. Indian J. Chem. 2001, 40B, 213.

  12. Said, M.; Abouzid, K.; Mouneer, A.; Ahmedy, A.; Osman, A. M. Arch. Pharm. Res. 2004, 27, 471.

    Article  CAS  Google Scholar 

  13. Duval, R.; Kolb, S.; Braud, E.; Genest, D.; Garbay, C. J. Comb. Chem. 2009, 11, 947.

    Article  CAS  Google Scholar 

  14. Kolb, S.; Mondésert, O.; Goddard, M. L.; Jullien, D.; Villoutreix, B. O.; Ducommun, B.; Garbay, C.; Braud, E. ChemMedChem 2009, 4, 633.

    Article  CAS  Google Scholar 

  15. Zhi, H.; Chen, L.; Zhang, L.; Liu, S.; Wan, D. C. C.; Lin, H.; Hu, C. ARKIVOC 2008, (xiii), 266.

  16. Rashad, A. E.; Shamroukh, A. H.; Abdel-Megeid, R. E.; El-Sayed, W. A. Synth. Commun. 2010, 40, 1149.

    Article  CAS  Google Scholar 

  17. El-Emary, T. I.; Abdel-Mohsen, S. A. Phosphorus, Sulfur Silicon Relat. Elem. 2006, 181, 2459.

  18. Maddila, S.; Damu, G. L. V.; Oseghe, E. O.; Abafe, O. A.; Venakata, R. C.; Lavanya, P. J. Korean Chem. Soc. 2012, 56, 334.

    Article  CAS  Google Scholar 

  19. (a) Tumkevicius, S.; Dodonova, J. Chem. Heterocycl. Compd. 2012, 48, 258. [Khim. Geterotsikl. Soedin. 2012, 275.] (b) Schindler, C.; Schulzke, C. Chem. Heterocycl. Compd. 2015, 51, 1008. [Khim. Geterotsikl. Soedin. 2015, 51, 1008.]

  20. (a) Sonogashira, K. J. Organomet. Chem. 2002, 653, 46. (b) Chinchilla, R.; Najera, C. Chem. Rev. 2007, 107, 874.

  21. Toyota, M.; Komori, C.; Ihara, M. J. Org. Chem. 2000, 65, 7110.

    Article  CAS  Google Scholar 

  22. Yoshimura, F.; Kawata, S.; Hirama, M. Tetrahedron Lett. 1999, 40, 8281.

    Article  CAS  Google Scholar 

  23. Miller, M. W.; Johnson, C. R. J. Org. Chem. 1997, 62, 1582.

    Article  CAS  Google Scholar 

  24. Sakai, A.; Aoyama, T.; Shioiri, T. Tetrahedron Lett. 1999, 40, 4211.

    Article  CAS  Google Scholar 

  25. Graham, A. E.; McKerrecher, D.; Davies, D. H.; Taylor, R. J. K. Tetrahedron Lett. 1996, 37, 7445.

    Article  CAS  Google Scholar 

  26. Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453.

    Article  CAS  Google Scholar 

  27. Wu, R.; Schumm, J. S.; Pearson, D. L.; Tour, J. M. J. Org. Chem. 1996, 61, 6906.

    Article  CAS  Google Scholar 

  28. Abele, E.; Belyakov, S.; Beresneva, T.; Golomba, L.; Abele, R. Chem. Heterocycl. Compd. 2016, 52, 140. [Khim. Geterotsikl. Soedin. 2016, 52, 140.]

  29. Larock, R. C.; Doty, M. J.; Cacchi, S. J. Org. Chem. 1993, 58, 4579.

    Article  CAS  Google Scholar 

  30. Belov, G. M.; Belov, D. S.; Kurkin, A. V.; Yurovskaya, M. A. Chem. Heterocycl. Compd. 2012, 48, 73. [Khim. Geterotsikl. Soedin. 2012, 78.]

  31. Roesch, K. R.; Larock, R. C. J. Org. Chem. 1998, 63, 5306.

    Article  CAS  Google Scholar 

  32. Larock, R. C.; Yum, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652.

    Article  CAS  Google Scholar 

  33. Gulevich, A. V.; Gevorgyan, V. Chem. Heterocycl. Compd. 2012, 48, 17. [Khim. Geterotsikl. Soedin. 2012, 22.]

  34. Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2004, 104, 3079.

    Article  CAS  Google Scholar 

  35. (a) Keivanloo, A.; Bakherad, M.; Rahimi, A.; Taheri, S. A. N. Tetrahedron Lett. 2010, 51, 2409. (b) Keivanloo, A.; Bakherad, M.; Rahimi, A. Synthesis 2010, 1599. (c) Bakherad, M.; Isfahani, H. N.; Keivanloo, A.; Doostmohammadi, N. Tetrahedron Lett. 2008, 49, 3819. (d) Bakherad, M.; Isfahani, H. N.; Keivanloo, A.; Sang, G. Tetrahedron Lett. 2008, 49, 6188.

  36. (a) Zanardi, A.; Mata, J. A.; Peris, E. Organometallics 2009, 28, 4335. (b) Raju, S.; Batchu, V. R.; Swamy, N. K.; Dev, R. V.; Sreekanth, B. R.; Babu, J. M.; Vyas, K.; Kumar, P. R.; Mukkanti, K.; Annamalai, P.; Pal, M. Tetrahedron 2006, 62, 9554. (c) Olivi, N.; Spruyt, P.; Peyrat, J.-F.; Alami, M.; Brion, J.- D. Tetrahedron Lett. 2004, 45, 2607. (d) Kundu, N. G.; Pal, M.; Mahanty, J. S.; De, M. J. Chem. Soc., Perkin Trans. 1 1997, 2815.

Download references

The authors would like to thank the Research Council of Shahrood University of Technology for the financial support of this work.

Author information

Authors and Affiliations

  1. School of Chemistry, Shahrood University of Technology, P.O. Box 36199-95161, Shahrood, Iran

    Ali Keivanloo, Mohammad Bakherad & Amir Hossein Amin

  2. Islamic Azad University, Saveh Branch, P.O. Box 39187-366, Saveh, Iran

    Taraneh Shahani

Authors
  1. Ali Keivanloo
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Mohammad Bakherad
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Taraneh Shahani
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Amir Hossein Amin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ali Keivanloo.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(10), 836–839

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Keivanloo, A., Bakherad, M., Shahani, T. et al. Pd-catalyzed coupling reaction of 6-hydroxy-2-(prop-2-yn-1-ylsulfanyl)pyrimidin-4(1H)-one with aryl iodides: efficient syntheses of new 3-benzylthiazolo[3,2-a]pyrimidinones. Chem Heterocycl Comp 52, 836–839 (2016). https://doi.org/10.1007/s10593-016-1974-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-016-1974-8

Keywords

Search

Navigation