Skip to main content
Log in

Pyridine-based, microwave-assisted one-pot synthetic protocol for the synthesis of ethyl 3-substituted-4-oxo-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

Pyridine has been used for one-pot, two-component synthesis of ethyl 3-substituted-4-oxo-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate derivatives in moderate to good yields by condensing N-substituted thioureas with diethyl ethoxymalonate under microwave irradiation.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Scheme 1
Scheme 2

Similar content being viewed by others

References

  1. I. Lieberman, A. Kornberg, E.S. Simms, J. Biol. Chem. 215, 403 (1955)

    CAS  Google Scholar 

  2. J. Victor, L.B. Greenberg, D.L. Sloan, J. Biol. Chem. 254, 2647 (1979)

    CAS  Google Scholar 

  3. G. Dodin, J.-E. Dubois, J. Am. Chem. Soc. 102, 3049 (1980)

    Article  CAS  Google Scholar 

  4. M.A. Lea, A. Luke, A. Assad, M. Patel, P.A. Reddy, Int. J. Biochem. 24, 1453 (1992)

    Article  CAS  Google Scholar 

  5. A. Garoufis, S.K. Hadjikakou, N. Hadjiliadis, Coord. Chem. Rev. 253, 1384 (2009)

    Article  CAS  Google Scholar 

  6. F. Hueso-Urena, M.N. Moreno-Carretero, J.M. Salas-Peregrin, G. Alvarez de Cienfuegos-Lopez, J. Inorg. Biochem. 43, 17 (1991)

    Article  CAS  Google Scholar 

  7. G. Maistralis, N. Katsaros, S.P. Perlepes, D. Kovala-Demertzi, J. Inorg. Biochem. 45, 1 (1992)

    Article  CAS  Google Scholar 

  8. F. Hueso-Ureña, M.N. Moreno-Carretero, J.M. Salas-Peregrin, G. Alvarez de Cienfuegos-Lopez, Trans. Met. Chem. 20, 262 (1995)

    Article  Google Scholar 

  9. S. Gore, S. Baskaran, B. Koenig, Green Chem. 13, 1009 (2011)

    Article  CAS  Google Scholar 

  10. B.G.S. Torres, F.D.T. Uchôa, R.F.S. Canto, A. Crestani, V. Eifler-Lima, T.D. Costa, Quim. Nova 37, 461 (2014)

    Article  CAS  Google Scholar 

  11. N.D. Moirangthem, W.S. Laitonjam, Indian J. Chem. 48B, 1023 (2009)

    CAS  Google Scholar 

  12. T.L.V. Ulbricht, C.C. Prince, Chem. Ind. 39, 1221 (1955)

    Google Scholar 

  13. W.W. Calvert, J.T. John, J. Am. Chem. Soc. 78, 5294 (1956)

    Article  Google Scholar 

  14. T. Hudlicky, Chem. Rev. 96, 3 (1996)

    Article  CAS  Google Scholar 

  15. P. Biginelli, Gazz. Chim. Ital. 23, 360 (1893)

    Google Scholar 

  16. R.L. Sawant, M.S. Bhatia, B. Chem, Soc. Ethiopia 22, 391 (2008)

    CAS  Google Scholar 

  17. E.H. Hu, D.R. Sidler, U.-H. Dolling, J. Org. Chem. 63, 3454 (1998)

    Article  CAS  Google Scholar 

  18. Y. Ma, C. Qian, L. Wang, M. Yang, J. Org. Chem. 65, 3864 (2000)

    Article  CAS  Google Scholar 

  19. W. Su, J. Li, Z. Zheng, Y. Shen, Tetrahedron Lett. 46, 6037 (2005)

    Article  CAS  Google Scholar 

  20. V. Radharani, N. Srinivas, M. Radha Kishan, S.J. Kulkarni, K.V. Raghavan, Green Chem. 3, 305 (2001)

    Article  Google Scholar 

  21. K. Folkers, T.B. Johnson, J. Am. Chem. Soc. 55, 2886 (1933)

    Article  CAS  Google Scholar 

  22. S.K. Sharma, P. Kumar, B. Narasimhan, K. Ramasamy, V. Mani, R.K. Mishra, A.B. Majeed, Eur. J. Med. Chem. 48, 16 (2012)

    Article  CAS  Google Scholar 

  23. M. Gohain, D. Prajapati, J.S. Sandhu, Synlett 2, 235 (2004)

    Google Scholar 

  24. X. Zhang, Y. Li, C. Liu, J. Wang, J. Mol. Catal. A: Chem. 253, 207 (2006)

    Article  CAS  Google Scholar 

  25. C. Friot, A. Reliquet, F. Reliquet, J.C. Meslin, Synthesis 5, 695 (2000)

    Article  Google Scholar 

  26. S.A. Shiba, M.M. Mohamed, M.A. Hassan, A.M. El-Sayed, Phosphorus Sulfur Silicon 158, 91 (2000)

    Article  CAS  Google Scholar 

  27. D. Landini, F. Montanari, A. Maia, J. Am. Chem. Soc. 100, 2796 (1978)

    Article  CAS  Google Scholar 

  28. J.E. Gorden, R.Z. Kutina, J. Am. Chem. Soc. 99, 3903 (1977)

    Article  Google Scholar 

  29. M.A. Hassan, M.M. Mohamed, S.A. Shiba, M.K. Abou El-Regal, A. Khalil, Phosphorus Sulfur Silicon Relat. Elem. 178, 2497 (2003)

    Article  CAS  Google Scholar 

  30. C.H. Soh, Y. Lam, J. Comb. Chem. 12, 286 (2010)

    Article  CAS  Google Scholar 

  31. S. Botsi, A. Tsolomitis, Heterocycl. Commun. 13, 229 (2011)

    Google Scholar 

  32. V. Nair, A.R. Sreekanth, N. Abhilash, A.T. Biju, B. Rema Devi, R.S. Menon, N.P. Rath, R. Srinivas, Synthesis 12, 1895 (2003)

    Article  Google Scholar 

  33. A.A. Esmaeili, H. Vesalipoor, R. Hosseinabadi, A.R. Fakhari, M.A. Naseri, E. Ghiamati, Tetrahedron Lett. 52, 4865 (2011)

    Article  CAS  Google Scholar 

  34. A.A. Esmaeili, F. Zarifi, A. Moradi, M. Izadyar, A.R. Fakhari, Tetrahedron Lett. 55, 333 (2014)

    Article  CAS  Google Scholar 

  35. A. Shaabani, A.H. Rezayan, A. Sarvary, H.R. Khavasi, Tetrahedron Lett. 49, 1469 (2008)

    Article  CAS  Google Scholar 

  36. R. Mahesh, S. Mundra, T. Devadoss, L.P. Kotra, Arab. J. Chem. (2014). doi:10.1016/j.arabjc.2014.11.008

    Google Scholar 

  37. S. Mundra, R. Mahesh, J. Young Pharm. 7, 96 (2015)

    Article  CAS  Google Scholar 

  38. S.K. Chakka, M. Kalamuddin, S. Sundararaman, L. Wei, S. Mundra, R. Mahesh, P. Malhotra, A. Mohmmed, L.P. Kotra, Bioorg. Med. Chem. 23, 2221 (2015)

    Article  CAS  Google Scholar 

  39. I. Papazoglou, P.J. Cox, A.G. Hatzidimitriou, C. Kokotidou, T. Choli-Papadopoulou, P. Aslanidis, Eur. J. Med. Chem. 78, 383 (2014)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors gratefully acknowledge the financial support from the Department of Biotechnology (BT/IN/Canada/22/AM/2009), New Delhi, India as a part of the ISTP Canada-DBT Collaborative R&D Program. Authors are also thankful to the Birla Institute of Technology & Science (BITS), Pilani, India, and SAIF, Panjab University, Chandigarh, India, for providing the infrastructure facilities and analytical facilities, respectively. The authors are grateful to Dr. L.P. Kotra (University Health Network, Toronto, Canada), Dr. Sai Kumar Chakka (Encycle Therapeutics, Toronto-Canada) and Dr. Asif Mohmmed (ICGEB, Delhi, India) for their valuable suggestions.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Sourabh Mundra.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Mundra, S., Mahesh, R. Pyridine-based, microwave-assisted one-pot synthetic protocol for the synthesis of ethyl 3-substituted-4-oxo-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates. Res Chem Intermed 42, 4207–4219 (2016). https://doi.org/10.1007/s11164-015-2270-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-015-2270-4

Keywords

Navigation