Skip to main content

Synthesis of oxindolyl-pyrimidines and oxindolyl-furopyrimidines from isatin-derived propargylic alcohols

Abstract

A Brønsted acid-catalyzed reaction of 6-amino uracil and isatin-derived propargylic alcohols for the synthesis of a series of oxindole-fused pyrimidine in good-to-high yields was achieved (up to 94%). Furthermore, the reaction of isatin-derived propargylic alcohols and 1,3-dimethylbarbituric acid or ethyl 3-aminocrotonate gave oxindoles containing furopyrimidine or pyrrole, respectively, in moderate-to-good yields under relatively mild reaction conditions.

Graphic abstract

A Brønsted acid-catalyzed reaction of 6-amino uracil, 1,3-dimethylbarbituric acid or ethyl 3-aminocrotonate with isatin-derived propargylic alcohols for the synthesis of oxindole-fused pyrimidine, furopyrimidine or pyrrole.

This is a preview of subscription content, access via your institution.

Fig. 1
Fig. 2
Scheme 1
Fig. 3
Scheme 2
Scheme 3
Scheme 4

References

  1. I.M. Lagoja, Chem. Biodivers. 2, 1 (2005)

    CAS  PubMed  Article  Google Scholar 

  2. F. Zhang, Y. Zhao, L. Sun, L. Ding, Y. Gu, P. Gong, Eur. J. Med. Chem. 46, 3149 (2011)

    CAS  PubMed  Article  Google Scholar 

  3. K. Undheim, T. Benneche, in Comprehensive Heterocyclic Chemistry, Chapter 2, vol. 6, ed. by A.R. Katritzky, C.W. Rees, E.V.F. Scriven (Pergamon Press, London, 1996), pp. 93–231

    Google Scholar 

  4. D.J. Brown, R.F. Evans, WB Cowden, in The Pyrimidines, vol. 52, ed. by E.C. Taylor, A. Weissberger (Wiley, New York, 1994)

    Google Scholar 

  5. M. Johar, T. Manning, D.Y. Kunimoto, R. Kumar, Bioorg. Med. Chem. 13, 6663 (2005)

    CAS  PubMed  Article  Google Scholar 

  6. N. Azas, P. Rathelot, S. Djekou, F. Delmas, A. Gellis, C. Di Giorgio, P. Vanelle, P. Timon-David, Il Farmaco 58, 1263 (2003)

    CAS  PubMed  Article  Google Scholar 

  7. A. Agarwal, K. Srivastava, S.K. Puri, P.M.S. Chauhan, Bioorg. Med. Chem. 13, 4645 (2005)

    CAS  PubMed  Article  Google Scholar 

  8. S. Tu, J. Zhang, X. Zhu, J. Xu, Y. Zhang, Q. Wang, R. Jia, B. Jiang, J. Zhang, Bioorg. Med. Chem. Lett. 16, 3578 (2006)

    CAS  PubMed  Article  Google Scholar 

  9. M. Adib, F. Peytam, M. Rahmanian-Jazi, Sh Mahernia, H.R. Bijanzadeh, M. Jahani, M. Mohammadi-Khanaposhtani, S. Imanparast, M.A. Faramarzi, M. Mahdavi, B. Larijani, Eur. J. Med. Chem. 155, 353 (2018)

    CAS  PubMed  Article  Google Scholar 

  10. J. Quiroga, C. Cisneros, B. Insuasty, R. Abonía, S. Cruz, M. Nogueras, J.M. de la Torre, M. Sortino, S. Zacchino, J. Heterocycl. Chem. 43, 299 (2006)

    CAS  Article  Google Scholar 

  11. Gh Imani Shakibaei, A. Feiz, H.R. Khavasi, A. Abolhasani Soorki, A. Bazgir, ACS Comb. Sci. 13, 96 (2011)

    Article  CAS  Google Scholar 

  12. D.L. Silverio, S. Torker, T. Pilyugina, E.M. Vieira, M.L. Snapper, F. Haeffner, A.H. Hoveyda, Nature 494, 216 (2013)

    CAS  PubMed  Article  PubMed Central  Google Scholar 

  13. G. Bergonzini, P. Melchiorre, Angew. Chem. Int. Ed. 51, 971 (2012)

    CAS  Article  Google Scholar 

  14. B. Yu, D.Q. Yu, H.M. Liu, Eur. J. Med. Chem. 97, 673 (2015)

    CAS  PubMed  Article  Google Scholar 

  15. Y. Zheng, C.M. Tice, S.B. Singh, Bioorg. Med. Chem. Lett. 24, 3673 (2014)

    CAS  PubMed  Article  Google Scholar 

  16. X. Liu, T. Feng, D. Wang, H. Liu, C. Yang, X. Li, B. Lin, Z. Zhao, Y. Zhou, Tetrahedron Lett. 57, 4113 (2016)

    CAS  Article  Google Scholar 

  17. R.V. Antre, A. Cendilkumar, D. Goli, G.S. Andhale, R.J. Oswal, Saudi Pharm. J. 19, 233 (2011)

    CAS  PubMed  Article  PubMed Central  Google Scholar 

  18. Q. Chen, Y. Tang, T. Huang, X. Liu, L. Lin, X. Feng, Angew. Chem. Int. Ed. 55, 5286 (2016)

    CAS  Article  Google Scholar 

  19. X.P. Fu, L. Liu, D. Wang, Y.J. Chen, ChJ Li, Green Chem. 13, 549 (2011)

    CAS  Article  Google Scholar 

  20. K. Dhara, A. Kapat, T. Ghosh, J. Dash, Synthesis 48, 4260 (2016)

    CAS  Article  Google Scholar 

  21. F. Lazreg, M. Lesieur, A.J. Samson, C.S.J. Cazin, ChemCatChem. 8, 209 (2016)

    CAS  Article  Google Scholar 

  22. M. Chouhan, K.R. Senwar, K. Kumar, R. Sharma, V.A. Nair, Synthesis 46, 195 (2014)

    Google Scholar 

  23. Y.W. Dong, G.W. Wang, L. Wang, Tetrahedron 64, 10148 (2008)

    CAS  Article  Google Scholar 

  24. H.J. Roh, J.W. Lim, J.Y. Ryu, J. Lee, J.N. Kim, Tetrahedron Lett. 57, 4280 (2016)

    CAS  Article  Google Scholar 

  25. N. Kumarswamyreddy, V. Kesavan, Eur. J. Org. Chem. 2016, 5301 (2016)

    Article  CAS  Google Scholar 

  26. S. Yaragorla, R. Dada, G. Singh, A. Pareek, M. Rana, A.K. Sharma, Chem. Select 1, 6902 (2016)

    CAS  Google Scholar 

  27. H.J.R. Su, Y.K. Beom, K.M. Jae, N. Kim, Tetrahedron Lett. 58, 21 (2017)

    Article  CAS  Google Scholar 

  28. I.R.S. Rahila, S. Shamim, P. Rai, M.A. Waseem, A.A.H. Abumhdi, Tetrahedron Lett. 54, 6991 (2013)

    Article  CAS  Google Scholar 

  29. N. Kumarswamyreddy, M. Prakash, S. Jayakumar, V. Kesavan, RSC Adv. 5, 54316 (2015)

    CAS  Article  Google Scholar 

  30. H.J. Roh, G. Kim, S. Cho, J.Y. Ryu, J. Lee, J.N. Kim, Tetrahedron Lett. 59, 1484 (2018)

    CAS  Article  Google Scholar 

  31. H.J. Roh, D.Y. Seo, J.Y. Ryu, J. Lee, J.N. Kim, Bull. Korean Chem. Soc. 38, 582 (2017)

    CAS  Article  Google Scholar 

  32. M.M. Heravi, B. Talaei, Advances in Heterocyclic Chemistry (Elsevier, Amsterdam, 2014), pp. 143–244

    Google Scholar 

  33. M.M. Heravi, B. Talaei, Advances in Heterocyclic Chemistry (Elsevier, Amsterdam, 2014), pp. 1–66

    Google Scholar 

  34. B. Talaei, M.M. Heravi, Advances in Heterocyclic Chemistry (Elsevier, Amsterdam, 2018), pp. 1–106

    Google Scholar 

  35. S. Khaghaninejad, M.M. Heravi, Advances in Heterocyclic Chemistry (Elsevier, Amsterdam, 2014), pp. 95–146

    Google Scholar 

  36. M.M. Heravi, V. Fathi Vavsari, Advances in Heterocyclic Chemistry (Elsevier, Amsterdam, 2015), pp. 77–145

    Google Scholar 

  37. M.M. Heravi, N. Montazeri, M. Rahimizadeh, M. Bakavoli, M. Ghassemzadeh, J. Heterocycl. Chem. 42, 1021 (2005)

    CAS  Article  Google Scholar 

  38. M.M. Heravi, A. Kivanloo, M. Rahimzadeh, M. Bakavoli, M. Ghassemzadeh, B. Neumüller, Tetrahedron Lett. 46, 1607 (2005)

    CAS  Article  Google Scholar 

  39. M. Saeedi, M.M. Heravi, Y.S. Beheshtiha, H.A. Oskooie, Tetrahedron 66, 5345 (2010)

    CAS  Article  Google Scholar 

  40. M.M. Heravi, M. Zakeri, A. Moharami, J. Chem. Sci. 124, 865 (2012)

    CAS  Article  Google Scholar 

  41. M. Daraie, Y.S. Beheshtiha, M.M. Heravi, Monatsh. Chem. 146, 191 (2015)

    CAS  Article  Google Scholar 

  42. NCCLS. Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria, which Grows Aerobically, 5th ed.; Approved Standard M7-A5 (NCCLS, Villanova, 2000)

Download references

Acknowledgements

The authors are thankful to Saramadan Elmi Iran federation for financial assistance. MMH and AB are appreciating the encouragements given by Alzahra University and Shahid Behershti University, respectively.

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Majid M. Heravi or Ayoob Bazgir.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 2033 kb)

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Heravi, M.M., Feiz, A., Notash, B. et al. Synthesis of oxindolyl-pyrimidines and oxindolyl-furopyrimidines from isatin-derived propargylic alcohols. J IRAN CHEM SOC 17, 1743–1751 (2020). https://doi.org/10.1007/s13738-020-01893-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13738-020-01893-3

Keywords

  • Propargylic alcohols
  • Amino uracil
  • Oxindolyl-pyrimidine
  • Oxindolyl-furopyrimidine
  • Oxindol