Skip to main content
Log in

l-Proline Derived Secondary Aminothiourea Organocatalyst for Synthesis of Coumarin Derived Trisubstituted Methanes: Rate Enhancement by Bifunctional Catalyst over Cooperative Catalysis

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

Although l-proline derived aminothioureas are being used as catalyst in asymmetric synthesis, their applications in multicomponent reactions are not yet reported in the literature. We report herein a l-proline derived secondary aminothiourea as a multifunctional catalyst in multicomponent reaction for synthesis of coumarin-based unsymmetrical trisubstituted methanes whose prototype has been found to be acetylcholinesterase inhibitor. The method requires low catalyst loading (5 mol%), very short reaction time (15–30 min) to give excellent yields. For the first time, it is observed that our bifunctional catalyst significantly increases the rate of conversion in comparison to that of two cooperative organocatalysts having similar catalytic sites.

Graphical Abstract

l-Proline derived secondary aminothiourea organocatalyst in multicomponent reaction: synthesis of coumarin derived trisubstituted methanes

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.

Institutional subscriptions

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

Similar content being viewed by others

References

  1. Mukherjee S, Yang JW, Hoffmann S, List B (2007) Chem Rev 107:5471

    Article  CAS  PubMed  Google Scholar 

  2. Saito S, Nakadai M, Yamamoto H (2001) Synlett 1245

  3. Mase N, Tanaka F, Barbas CF III (2003) Org Lett 5:4369

    Article  CAS  PubMed  Google Scholar 

  4. Mase N, Tanaka F, Barbas CF III (2004) Angew Chem Int Ed 43:2420

    Article  CAS  Google Scholar 

  5. Tang Z, Jiang F, Yu L-T, Cui X, Gong L-Z, Mi A-Q, Jiang Y-Z, Wu Y-D (2003) J Am Chem Soc 125:5262

    Article  CAS  PubMed  Google Scholar 

  6. Tang Z, Jiang F, Cui X, Gong L-Z, Mi A-Q, Jiang Y-Z, Wu Y-D (2004) Proc Natl Acad Sci USA 101:5755

    Article  CAS  PubMed  Google Scholar 

  7. Torii H, Nakadai M, Ishihara K, Saito S, Yamamoto H (2004) Angew Chem Int Ed 43:1983

    Article  CAS  Google Scholar 

  8. Berkessel A, Koch B, Lex J (2004) Adv Synth Catal 346:1141

    Article  CAS  Google Scholar 

  9. Silva F, Sawicki M, Gouverneur V (2006) Org Lett 8:5417

    Article  CAS  PubMed  Google Scholar 

  10. Obregón-Zúñiga A, Milán M, Juaristi E (2017) Org Lett 19:1108

    Article  CAS  PubMed  Google Scholar 

  11. Hernández JG, Juaristi E (2012) Chem Commun 48:5396

    Article  CAS  Google Scholar 

  12. Serdyuk OV, Heckel CM, Tsogoeva SB (2013) Org Biomol Chem 11:7051

    Article  CAS  PubMed  Google Scholar 

  13. Siau W-Y, Wang J (2011) Catal Sci Technol 1:1298

    Article  CAS  Google Scholar 

  14. Fu J-Y, Huang Q-C, Wang Q-W, Wang L-X, Xu X-Y (2010) Tetrahedron Lett 51:4870

    Article  CAS  Google Scholar 

  15. Demir AS, Basceken S (2013) Tetrahedron Asymm 24:515

    Article  CAS  Google Scholar 

  16. Kokotos C (2012) J Org Chem 77:1131

    Article  CAS  PubMed  Google Scholar 

  17. Fotaras S, Kokotos CG, Kokotos G (2012) Org Biomol Chem 10:5613

    Article  CAS  PubMed  Google Scholar 

  18. Khandelwal S, Tailor YK, Kumar M (2016) Current Organocatal 3:176

    Article  CAS  Google Scholar 

  19. Clarke CJ, Tu W-C, Levers O, Bröhl A, Hallett JP (2018) Chem Rev 118:747

    Article  CAS  PubMed  Google Scholar 

  20. Peng XM, Damu GLV, Zhou C-H (2013) Curr Pharm Des 19:3884

    Article  CAS  PubMed  Google Scholar 

  21. Craig LA, Hong NS, McDonald RJ (2011) Neurosci Biobehav Rev 35:1397

    Article  CAS  PubMed  Google Scholar 

  22. Francis PT, Palmer AM, Snape M, Wilcock GK (1999) J Neurol Neurosurg Psychiatry 66:137

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  23. Peters J, Trovaslet M, Trapp M, Nachon F, Hill F, Royer E, Tehei M (2012) Phys Chem Chem Phys 14:6764

    Article  CAS  PubMed  Google Scholar 

  24. Baruah P, Basumatary G, Yesylevskyy SO, Aguan K, Bez G, Mitra S (2018) J Bimol Struct Dyn. https://doi.org/10.1080/07391102.2018.1465853

  25. Bharti R, Parvin T (2015) Synth Commun 45:1442

    Article  CAS  Google Scholar 

  26. Bharti R, Parvin T (2015) RSC Adv 5:66833

    Article  CAS  Google Scholar 

  27. Bentley TW (2011) Org Biomol Chem 9:6685

    Article  CAS  PubMed  Google Scholar 

  28. Wang W-H, Abe T, Wang X-B, Kodama K, Hirose T, Zhang G-Y (2010) Tetrahedron 21:2925

    Article  CAS  Google Scholar 

  29. Pedrosa R, Andrés JM, Gamarra A, Manzano R, Pérez-López C (2013) Tetrahedron 69:10811

    Article  CAS  Google Scholar 

  30. Appel R, Chelli S, Tokuyasu T, Troshin K, Mayr H (2013) J Am Chem Soc 135:6579

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgements

The analytical services provided by Sophisticated Analytical Instrumentation Facility (SAIF), North Eastern Hill University, Shillong, India are acknowledged.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Ghanashyam Bez.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1—Spectroscopic data for all the compounds (DOCX 6445 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Basumatary, G., Mohanta, R. & Bez, G. l-Proline Derived Secondary Aminothiourea Organocatalyst for Synthesis of Coumarin Derived Trisubstituted Methanes: Rate Enhancement by Bifunctional Catalyst over Cooperative Catalysis. Catal Lett 149, 2776–2786 (2019). https://doi.org/10.1007/s10562-019-02809-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-019-02809-4

Keywords

Navigation