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Synthesis of xanthene and coumarin derivatives in water by using β-Cyclodextrin

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Abstract

Simple and green procedure was developed for the synthesis of various xanthene and coumarin derivatives using beta-cyclodextrin (β-CD) as reusable catalyst at 70 °C in water. Condensation of salicylaldehyde (1 mmol) and dimedone (2 mmol) or 1,3 cyclohexadione (2 mmol) gave corresponding xanthene derivatives, while condensation of salicylaldehyde (1 mmol) with Meldrum’s acid (1 mmol) or 4-Hydroxy-6-methyl-2H-pyran-2-one (1 mmol) gave respective coumarin derivatives in impressive yields. Involvement of β-CD as catalyst was ascertained by inclusion complex evaluation of β-CD-salicylaldehyde with 1H NMR analysis at 70 °C.

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References

  1. A. Chaudhary, J.M. Khurana, Curr. Org. Synth. 15, 341 (2018)

    CAS  Google Scholar 

  2. P. Mane, B. Shinde, P. Mundada, V. Gawade, B. Karale, A. Burungale, Res. Chem. Intermed. 46, 231 (2020)

    CAS  Google Scholar 

  3. K.M. Khan, I. Khan, S. Perveen, M.I. Malik, J. Fluorine Chem. 158, 1 (2014)

    CAS  Google Scholar 

  4. D. Prasad, A. Preetam, M. Nath, C. R. Chimie. 16, 1153 (2013)

    CAS  Google Scholar 

  5. L. Nagarapu, S. Karnakanti, R. Bantu, R. Bantu, B. Sridhar, Synth. Commun. 42, 967 (2012)

    CAS  Google Scholar 

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

    CAS  Google Scholar 

  7. H.F. Niya, N. Hazeri, M. Fatahpour, M.T. Maghsoodlou, Res. Chem. Intermed. 46, 3651 (2020)

    Google Scholar 

  8. D. Thirumalai, S. Gajalakshmi, Res. Chem. Intermed. 46, 2657 (2020)

    CAS  Google Scholar 

  9. M.M. Heravi, P. Ansari, M. Saeed, N. Karimi, N. Tavakoli-Hosseini, Bull. Chem. Soc. Ethiop. 25, 315 (2011)

    CAS  Google Scholar 

  10. M. Salami, A. Ezabadi, Res. Chem. Intermed. 46, 4611 (2020)

    CAS  Google Scholar 

  11. S.E.S.M.M.A. SorkhiHashemiEzabadi, Res. Chem. Intermed. 46, 2229 (2020)

    Google Scholar 

  12. E. Yoshioka, S. Kohtani, H. Miyabe, Angew. Chem. Int. Ed. 50, 6638 (2011)

    CAS  Google Scholar 

  13. B.S. Kuarm, J.V. Madhav, S.V. Laxmi, B. Rajitha, Y.T. Reddy, P.N. Reddy, P.A. Crooks, Synth. Commun. 41(12), 1719–1724 (2011)

    CAS  Google Scholar 

  14. G. Sabitha, K. Arundhathi, K. Sudhakar, B.S. Sastry, J.S. Yadav, Synth. Commun. 38, 3439 (2008)

    CAS  Google Scholar 

  15. P. Zhang, Y. Yu, Z. Zhang, Synth. Commun. 38, 4474 (2008)

    CAS  Google Scholar 

  16. X. Wang, D. Shi, Y. Li, H. Chen, X. Wei, Z. Zong, Synth. Commun. 97, 35 (2005)

    Google Scholar 

  17. D.M. Pore, T.S. Shaikh, K.A. Undale, D.S. Gaikwad, C. R. Chimie. 13, 1429 (2010)

    CAS  Google Scholar 

  18. D. Shi, Y. Wang, Z. Lu, G. Dai, Synth. Commun. 30, 713 (2000)

    CAS  Google Scholar 

  19. L. Bonsignore, G. Loy, D. Secci, A. Calignano, Eur. J. Med. Chem. 28, 517 (1993)

    CAS  Google Scholar 

  20. K.A. Ohemeng, C.F. Schwender, K.P. Fu, J.F. Barrett, Bioorg. Med. Chem. Lett. 3, 225 (1993)

    CAS  Google Scholar 

  21. A. Mitra, S.K. Misra, A. Patra, Synth. Commun. 10, 915 (1980)

    CAS  Google Scholar 

  22. S. Kumar, R. Girl, S.C. Mishra, M.K. Machwe, Spectrochim. Acta, Part A 51, 1459 (1995)

    Google Scholar 

  23. W.C. Sun, K.R. Gee, R.P. Haugland, Bioorg. Med. Chem. Lett. 8, 3107 (1998)

    CAS  PubMed  Google Scholar 

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

    CAS  Google Scholar 

  25. N.N. Karade, S.V. Gampawar, S.V. Shinde, W.N. Jadhav, Chin. J. Chem 25, 1686 (2007)

    CAS  Google Scholar 

  26. G. Sabitha, N. Fatima, E.V. Reddy, J.S. Yadav, Adv. Synth. Catal 347(10), 1353–1355 (2005)

    CAS  Google Scholar 

  27. A. Shaabani, R. Ghadari, A. Rahmati, A.H. Rezayan, J. Iran. Chem. Soc. 6, 710 (2009)

    CAS  Google Scholar 

  28. D.-Q. Shi, Y. Zhou, S.-F. Rong, Synth. Commun. 39, 3500 (2009)

    CAS  Google Scholar 

  29. K. A. Undale, D. S. Gaikwad, T. S. Shiakh, U. V. Desai, D. M. Pore, Indian J. Chem., Sect B 51B, 1039 (2012)

  30. H. Xinwei, S. Yongjia, Z. Yao, Y. Zhiyu, H. Guang, J. Wenjing, C. Jiaojiao, Tetrahedron 71, 863 (2015)

    Google Scholar 

  31. J. Safaei-Ghomi, Z. Akbarzadeh, R. Teymuri, Res. Chem. Intermed. 45, 3425 (2019)

    CAS  Google Scholar 

  32. M.H. Sayahi, S. Bahadorikhalili, S.J. Saghanezhad, M.A. Miller, M. Mahdavi, Res. Chem. Intermed. 46(1), 491–507 (2020)

    CAS  Google Scholar 

  33. M. Torabi, M. Yarie, F. Karimi, M.A. Zolfigol, Res. Chem. Intermed. 291–16(2020).

    Google Scholar 

  34. G. Crini, Chem. Rev. 114, 10940 (2014)

    CAS  PubMed  Google Scholar 

  35. W. Zhao, Q. Zhong, J. Incl. Phenom. Macrocycl. Chem. 72, 1 (2012)

    CAS  Google Scholar 

  36. K. Takahashi, Chem. Rev. 98, 2013 (1998)

    CAS  PubMed  Google Scholar 

  37. Y. Chen, L. Yu, Chem. Soc. Rev. 39, 495 (2010)

    CAS  PubMed  Google Scholar 

  38. A. Patil, S. Gajare, G. Rashinkar, R. Salunkhe, Catal. Lett. 150, 127 (2020)

    CAS  Google Scholar 

  39. S. Sadjadi, M.M. Heravi, M. Daraie, Res. Chem. Intermed. 43, 843 (2017)

    CAS  Google Scholar 

  40. M.J. Nasab, A.R. Kiasat, Res. Chem. Intermed. 44, 2719 (2018)

    Google Scholar 

  41. N. Mohammadian, B. Akhlaghinia, Res. Chem. Intermed. 45, 4737 (2019)

    CAS  Google Scholar 

  42. M.R. Bhosle, S.A. Joshi, G.M. Bondle, J.N. Sangshetti, Res. Chem. Intermed. 46, 737 (2020)

    CAS  Google Scholar 

  43. R. Kardooni, A.R. Kiasat, N.E. Sabzi, Res. Chem. Intermed. 46, 1857 (2020)

    CAS  Google Scholar 

Download references

Acknowledgement

We gratefully acknowledge the financial support from the University Grants Commission (UGC), New Delhi, India for BSR-SAP fellowship No.F.7-183/2007(BSR), Dated 27th Jan. 2014.

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Correspondence to Siddharth R. Kamat.

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Kamat, S.R., Mane, A.H., Patil, A.D. et al. Synthesis of xanthene and coumarin derivatives in water by using β-Cyclodextrin. Res Chem Intermed 47, 911–924 (2021). https://doi.org/10.1007/s11164-020-04308-3

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