Skip to main content
SpringerLink
Log in

Chickpea leaf exudates (CLE) mediated Knoevenagel–Michael reactions for the synthesis of diketodiols and biscoumarins

Research on Chemical Intermediates volume 48, pages 2181–2198 (2022)Cite this article

Abstract

A green, highly efficient, and eco-friendly protocol for Knoevenagel–Michael addition reaction is reported in Chickpea leaf exudates (CLE) as a naturally sourced biosurfactant. The reactions between dimedone/4-hydroxycoumarins and a variety of aryl aldehydes were carried out in presence of CLE to afford diketodiols/biscoumarins. The synthetic pathway complies with several key requirements of green chemistry principles such as the employment of natural feedstock as green reaction media, ambient temperature, atom economy along with natural biosurfactant type Bronsted acids, and recyclable and biodegradable catalyst which led to a 28-fold increase in molar efficiency versus industrial standard protocols. Its dynamic phase is confirmed by the optical microscopy technique and critical micelle concentration measurement. The notable advantages of the present protocol were simple work-up procedure, high yield within short reaction time, easy separation of products, avoiding tedious column chromatography thus making the protocol environmentally friendly, sustainable, and economical.

Graphical abstract

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

Access options

Buy single article

Instant access to the full article PDF.

USD 39.95

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

Fig. 1
Scheme 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Scheme 2
Fig. 9
Fig. 10

References

  1. P. Tundo, P.T. Anastas, Green Chemistry: Theory and Practice, 1st edn. (Oxford University Press, Oxford, 1998)

    Google Scholar 

  2. H.C. James, J.M. Duncan, Handbook of Green Chemistry and Technology (Wiley-Blackwell Publishing, Hoboken, 2002), p. 564

  3. G. Yanlong, Green Chem. 14, 2091 (2012)

    Article  CAS  Google Scholar 

  4. L. Chao, T.A. Paul, Chem. Soc. Rev. 41, 1413 (2012)

    Article  CAS  Google Scholar 

  5. B.R. Dhevalapally, J. Org. Chem. 72(14), 5056 (2007)

    Article  CAS  Google Scholar 

  6. M.B. Arias, M.T. Albarran, I.P. Martinez, F.M. Martinez, G. Espinosa, E. Molins, E. Espinosa, J. Chem. Crystallogr. 29, 759 (1999)

    Article  Google Scholar 

  7. P. Shanmugasundaram, K.J. Prabahar, V.T. Ramakrishnan, J. Heterocycl. Chem. 30, 1003 (1993)

    Article  CAS  Google Scholar 

  8. S.T. Morbale, S.D. Jadhav, M.B. Deshmukh, S.S. Patil, RSC Adv. 5, 84610 (2015)

    Article  CAS  Google Scholar 

  9. S.T. Morbale, S.K. Shinde, S.A. Damate, M.B. Deshmukh, S.S. Patil, Lett. Org. Chem. 15, 57 (2018)

    CAS  Google Scholar 

  10. H.V. Chavan, B.P. Bandgar, ACS Sustain. Chem. Eng. 1, 929 (2013)

    Article  CAS  Google Scholar 

  11. B.M. Patil, S.K. Shinde, A.A. Jagdale, S.D. Jadhav, S.S. Patil, Res. Chem. Intermed. 47, 4369 (2021)

    Article  CAS  Google Scholar 

  12. K.M. Khan, G.M. Maharvi, M.T.H. Khan, A.J. Shaikh, S. Perveen, S. Begum, M.I. Choudhary, Bioorg. Med. Chem. 14, 344 (2006)

    Article  CAS  PubMed  Google Scholar 

  13. G.M. Maharvi, S. Ali, N. Riaz, N. Afza, A. Malik, M. Ashraf, M. Lateef, J. Enzyme. Inhib. Med. Chem. 23, 62 (2008)

    Article  CAS  PubMed  Google Scholar 

  14. R. Zhang, T. Futagoishi, M. Murata, A. Wakamiya, Y. Murata, J. Am. Chem. Soc. 136, 8193 (2014)

    Article  CAS  PubMed  Google Scholar 

  15. I. Manolov, C.M. Moessmer, N. Danchev, Eur. J. Med. Chem. 41, 882 (2006)

    Article  CAS  PubMed  Google Scholar 

  16. S.S. Li, Z. Gao, X. Feng, S.M. Hecht, J. Nat. Prod. 9, 1608 (2004)

    Article  CAS  Google Scholar 

  17. K.M. Khan, S. Iqbal, M.A. Lodhi, G.M. Maharvi, Z. Ullah, M.I. Choudhary, A.U. Rahman, S. Perveen, Bioorg. Med. Chem. 12, 1963 (2004)

    Article  CAS  PubMed  Google Scholar 

  18. S. Han, F.F. Zhang, H.Y. Qian, L.L. Chen, J.B. Pu, X. Xie, J.J. Chen, J. Med. Chem. 58, 5751 (2015)

    Article  CAS  PubMed  Google Scholar 

  19. N. Srividya, P. Ramamurthy, P. Shanmugasundaram, V.T. Ramakrishnan, J. Org. Chem. 61, 5083 (1996)

    Article  CAS  Google Scholar 

  20. H.S.P. Rao, V.S. Tangeti, J. Chem. Sci. 125, 777 (2013)

    Article  CAS  Google Scholar 

  21. J.M. Khurana, K. Vij, J. Chem. Sci. 124, 907 (2012)

    Article  CAS  Google Scholar 

  22. B. Maleki, M. Raei, H. Alinezhad, R. Tayebee, A. Sedropoushan, Org. Prep. Proced. Inter. 50, 288 (2018)

    Article  CAS  Google Scholar 

  23. V.K. Rao, M.M. Kumar, A. Kumar, Indian J. Chem. 50B, 1128 (2011)

    CAS  Google Scholar 

  24. Y. Ren, B. Yang, X. Liao, RSC Adv. 6, 22034 (2016)

    Article  CAS  Google Scholar 

  25. B.M. Sapkal, P.K. Labhane, J.R. Satam, Res. Chem. Intermed. 43, 4967 (2017)

    Article  CAS  Google Scholar 

  26. S.S. Ganesan, J. Kothandapani, A. Ganesan, Lett. Org. Chem. 11, 9 (2014)

    Article  CAS  Google Scholar 

  27. J.K. Rajput, G. Kaur, Catal. Sci. Technol. 4, 142 (2014)

    CAS  Google Scholar 

  28. M. Tajbakhsh, M. Heidary, R. Hosseinzadeh, Res. Chem. Intermed. 42, 1425 (2015)

    Article  CAS  Google Scholar 

  29. A. Ilangovan, S. Muralidharan, P. Sakthivel, S. Malayappasamy, S. Karuppusamy, M.P. Kaushik, Tetrahedron Lett. 54, 491 (2013)

    Article  CAS  Google Scholar 

  30. S. Kantevari, R. Bantu, L. Nagarapu, J. Mole. Cat. A: Chem. 269, 53 (2007)

    Article  CAS  Google Scholar 

  31. B. Pawar, V. Shinde, A. Chaskar, Green Sus. Chem. 3, 56 (2013)

    Article  CAS  Google Scholar 

  32. J. Albadi, A. Mansournezhad, S. Salehnasab, Res. Chem. Intermed. 41, 5713 (2014)

    Article  CAS  Google Scholar 

  33. J.M. Khurana, S. Kumar, Tetrahedron Lett. 50, 4125 (2009)

    Article  CAS  Google Scholar 

  34. J.M. Khurana, S. Kumar, Monatsh Chem. 141, 561 (2010)

    Article  CAS  Google Scholar 

  35. R. Karimian, F. Piri, A.A. Safari, S.J. Davarpanah, J. Nano. Chem. 3, 52 (2013)

    Article  Google Scholar 

  36. K. Tabatabaeian, H. Heidari, A. Khorshidi, M. Mamaghani, N.O. Mahmoodi, J. Serbian Chem. Soc. 77, 407 (2012)

    Article  CAS  Google Scholar 

  37. Z.N. Siddiqui, F. Farooq, Catal. Sci. Technol. 1, 810 (2011)

    Google Scholar 

  38. M. Kidwai, V. Bansal, P. Mothsra, S. Saxena, R.K. Somvanshi, S. Dey, T.P. Singh, J. Mole. Cat. A: Chem. 268, 76 (2007)

    Article  CAS  Google Scholar 

  39. S.R. Mali, S.K. Shinde, S.A. Damte, S.S. Patil, R. Soc. Open Sci. 5, 170333 (2018)

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  40. R.C. Patil, S.A. Damate, D.N. Zambare, S.S. Patil, New J. Chem. 45, 9152 (2021)

    Article  CAS  Google Scholar 

  41. P.W. Chia, B.S. Lim, F.S.J. Yong, S.C. Poh, S.Y. Kan, Environ. Chem. Lett. 16, 1493 (2018)

    Article  CAS  Google Scholar 

  42. D. Das, Tetrahedron Lett. 61, 152298 (2020)

    Article  CAS  Google Scholar 

  43. D. Sarmah, K.K. Borah, U. Bora, Sustain. Chem. Pharm. 24, 100551 (2021)

    Article  Google Scholar 

  44. K. Venkateswarlu, Environ. Chem. Lett. 19, 3887 (2021)

    Article  CAS  Google Scholar 

  45. M. Sarmah, M. Mondal, U. Bora, ChemistrySelect 2, 5180 (2017)

    Article  CAS  Google Scholar 

  46. R.C. Patil, U.P. Patil, A.A. Jagdale, S.K. Shinde, S.S. Patil, Res. Chem. Intermed. 46, 3527 (2020)

    Article  CAS  Google Scholar 

  47. R.C. Patil, S.K. Shinde, U.P. Patil, A.T. Birajdar, S.S. Patil, Res. Chem. Intermed. 47, 1675 (2021)

    Article  CAS  Google Scholar 

  48. R.C. Patil, A.A. Jagdale, U.P. Patil, J.S. Ghodake, S.S. Mali, C.K. Hong, S.S. Patil, Catal. Lett. 151, 3617 (2021)

    Article  CAS  Google Scholar 

  49. A. Ilangovan, S. Malayappasamy, S. Muralidharan, S. Maruthamuthu, Chem. Cent. J. 5, 81 (2011)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  50. K. Nikoofar, F.M. Yielzoleh, J. Saudi Chem. Soc. 22, 715 (2018)

    Article  CAS  Google Scholar 

  51. S. Ogo, Y. Takebe, K. Uehara, T. Yamazaki, H. Nakai, Y. Watanabe, S. Fukuzumi, Organometallics 25, 331 (2006)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

One of the authors Rupesh C. Patil is grateful to SARTHI, Pune (Government of Maharashtra) for the award of CMSRF-2019 fellowship [CIN-U74999PN2018NPL177394, dated 11th Sept. 2019]. The authors are also thankful to Shivaji University, Kolhapur and Indian Institute of Chemical Technology (IICT), Hyderabad, for spectral analysis.

Author information

Authors and Affiliations

  1. Synthetic Research Laboratory, PG Department of Chemistry, PDVP College (Affiliated to Shivaji University, Kolhapur), Tasgaon, Sangli, MS, 416312, India

    Rupesh C. Patil, Shashikant A. Damate, Ashutosh A. Jagdale, Snehali R. Mali, Sachinkumar K. Shinde & Suresh S. Patil

  2. Department of Chemistry, Kisan Veer Mahavidyalaya (Affiliated to Shivaji University, Kolhapur), Wai, Satara, MS, 412803, India

    Dnyandev N. Zambare

Authors
  1. Rupesh C. Patil
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Dnyandev N. Zambare
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Shashikant A. Damate
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Ashutosh A. Jagdale
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Snehali R. Mali
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Sachinkumar K. Shinde
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Suresh S. Patil
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Rupesh C. Patil.

Ethics declarations

Conflicts of interest

There are no conflicts interests to declare.

Additional information

Publisher's Note

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

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 3909 KB)

Rights and permissions

Reprints and Permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Patil, R.C., Zambare, D.N., Damate, S.A. et al. Chickpea leaf exudates (CLE) mediated Knoevenagel–Michael reactions for the synthesis of diketodiols and biscoumarins. Res Chem Intermed 48, 2181–2198 (2022). https://doi.org/10.1007/s11164-022-04707-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-022-04707-8

Keywords

search

Navigation