Skip to main content
Log in

Catalytic synthesis of dihydropyridines by domino reaction of terminal alkynes, carbodiimides, and acetylenic esters

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

Abstract

A novel additive-assisted reaction for the synthesis of dihydropyridines using copper salts as catalyst has been described. The (imino)pyridine skeletons were obtained in acceptable yields through a domino reaction involving terminal alkynes, carbodiimides, and acetylenic esters. Control experiments were conducted to explore the reaction path and to prove the mechanism proposed for the reaction.

Graphic abstract

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.

Similar content being viewed by others

References

  1. Alizadeh A, Rezvanian A, Zhu LG (2012) J Org Chem 77:4385

    Article  CAS  Google Scholar 

  2. Zhi S, Ma X, Zhang W (2019) Org Biomol Chem 17:7632

    Article  CAS  Google Scholar 

  3. Yu S, Wu J, Lan H, Gao L, Qian H, Fan K, Yin Z (2020) Org Lett 22:102

    Article  CAS  Google Scholar 

  4. Insuasty D, Castillo J, Becerra D, Rojas H, Abonia R (2020) Molecules 25:505

    Article  Google Scholar 

  5. Padwa A, Bur SK (2007) Tetrahedron 63:5341

    Article  CAS  Google Scholar 

  6. Echavarren AM, Jiaoc N, Gevorgyand V (2016) Chem Soc Rev 45:44452

    Article  Google Scholar 

  7. Jiang B, Tu XJ, Wang X, Tu SJ, Li G (2014) Org Lett 16:3656

    Article  CAS  Google Scholar 

  8. De Luca M, Ioele G, Ragno G (2019) Pharmaceutics 11:85

    Article  Google Scholar 

  9. Wang AL, Iadecola C, Wang G (2017) J Geriatr Cardiol 14:67

    CAS  PubMed  PubMed Central  Google Scholar 

  10. Sharma VK, Singh SK (2017) RSC Adv 7:2682

    Article  CAS  Google Scholar 

  11. Tejedor D, Cotos L, Méndez-Abt G, García-Tellado F (2014) J Org Chem 79:10655

    Article  CAS  Google Scholar 

  12. Bull JA, Mousseau JJ, Pelletier G, Charette AB (2012) Chem Rev 112:2642

    Article  CAS  Google Scholar 

  13. Yan X, Ling F, Zhang Y, Ma C (2015) Org Lett 17:3536

    Article  CAS  Google Scholar 

  14. Trinchera P, Sun W, Smith JE, Palomas D, Crespo-Otero R, Jones CR (2017) Org Lett 19:4644

    Article  CAS  Google Scholar 

  15. Gibson VC, Redshaw C, Solan GA (2007) Chem Rev 107:1745

    Article  CAS  Google Scholar 

  16. Yavari I, Souri S (2007) Synlett 2007:2969

    Article  Google Scholar 

  17. Samzadeh-Kermani A (2016) Synlett 27:461

    Article  CAS  Google Scholar 

  18. Serry AM, Luik S, Laufer S, Abadi AH (2010) J Comb Chem 12:559

    Article  CAS  Google Scholar 

  19. Zhou F, Liu X, Zhang N, Liang Y, Zhang R, Xin X, Dong D (2013) Org Lett 15:5786

    Article  CAS  Google Scholar 

  20. Kong L, Huang R, He H, Fan Y, Lin J, Yan S (2020) Green Chem 22:256

    Article  CAS  Google Scholar 

  21. Ramaraju P, Mir NA, Singh D, Gupta VK, Kant R, Kuma I (2015) Org Lett 17:5582

    Article  CAS  Google Scholar 

  22. Beigi-Somar V, Homami SS, Ghazanfarpour-Darjani M, Monzavi AH (2020) Monatsh Chem 151:231

    Article  CAS  Google Scholar 

  23. Samzadeh-Kermani A (2020) J Heterocycl Chem 57:248

    Article  CAS  Google Scholar 

  24. Samzadeh-Kermani A, Ghasemi S (2019) J Heterocycl Chem 56:2202

    Article  CAS  Google Scholar 

  25. Xu X, Gao J, Cheng D, Li J, Qiang G, Guoa H (2008) Adv Synth Catal 350:61

    Article  CAS  Google Scholar 

  26. Jahanshad M, Manafi M, Mousavi-Safavi SM, Homami SS, Ghazanfarpour-Darjani M (2020) Monatsh Chem 151:113

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We wish to thank for a grant from the Islamic Azad University, South Tehran Branch.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Mohammadreza Manafi.

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

Jalali, M.S., Manafi, M., Homami, S.S. et al. Catalytic synthesis of dihydropyridines by domino reaction of terminal alkynes, carbodiimides, and acetylenic esters. Monatsh Chem 151, 1173–1181 (2020). https://doi.org/10.1007/s00706-020-02655-w

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-020-02655-w

Keywords

Navigation