SpringerLink
Log in

Synthesis of 1, 8-dioxodecahydroacridines via Hantzsch condensation using theophylline in an aqueous medium: an eco-friendly and bio-based approach

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

In this work, we explored the convenient and sustainable method for the synthesis of 1, 8 dioxodecahydroacridine derivatives was achieved via a one-pot condensation reaction of dimedone, para-nitrobenzaldehyde, and ammonium acetate by using theophylline as a catalyst at room temperature in aqueous medium. This environmentally friendly method boasts several notable features, including high product yields, rapid completion of reactions, the use of eco-friendly and bio-based catalysts, straightforward work-up procedures without the need for column chromatography, cost-effectiveness, clean synthesis practices that avoid the use of harmful organic solvents, and exceptional atom efficiency.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Scheme 1.
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7

Similar content being viewed by others

Data availability

Data will be made available on request.

References

  1. G. Vasuki, K. Kumaravel, Tetrahedron Lett. 49, 5636–5638 (2008)

    Article  CAS  Google Scholar 

  2. M.K. Kenarl, S. Asgharl, B. Malekl et al., Res. Chem. Intermed. (2023). https://doi.org/10.1007/s11164-023-05165-6

    Article  Google Scholar 

  3. H. Atharifar, A. Keivanloo, B. Maleki et al., Res. Chem. Intermed. (2023). https://doi.org/10.1007/s11164-023-05152-x

    Article  Google Scholar 

  4. A. Sapkal, S. Attar, A. Kadam et al., Polycycl. Aromat. Compd. 43, 7719–7731 (2023)

    Article  CAS  Google Scholar 

  5. A. Sapkal, S. Kamble, J. Heterocycl. Chem. 57, 3597–3604 (2020)

    Article  CAS  Google Scholar 

  6. S.K. Tiwari, K.N. Shivhare, M.K. Patel et al., Polycycl. Aromat. Compd. 42, 1035–1047 (2022)

    Article  CAS  Google Scholar 

  7. D. Verma, V. Sharma, S. Jain et al., J. Dispers. Sci. Technol. 41, 1145–1158 (2020)

    Article  CAS  Google Scholar 

  8. W.A. Denny, Curr. Med. Chem. 9, 1655–1665 (2022)

    Google Scholar 

  9. M. Demeunynck, F. Charmantray, A. Martelli, Curr. Pharm. Des. 7, 1703–1724 (2001)

    Article  CAS  PubMed  Google Scholar 

  10. M.O. Anderson et al., Bioorg. Med. Chem. 14, 334–343 (2006)

    Article  CAS  PubMed  Google Scholar 

  11. Y. Mikata, M. Chikira, S. Yano et al., Inorgan. Chem. Acta. 279, 51–57 (1998)

    Article  CAS  Google Scholar 

  12. B. Das, P. Thirupathi, I. Mahender, V.S. Reddy et al., J. Mol. Catal. 247, 233–239 (2006)

    Article  CAS  Google Scholar 

  13. S.M. Vahdat et al., Arab. J. Chem. 12, 1515–1521 (2019)

    Article  CAS  Google Scholar 

  14. B. Maleki, R. Tayebee, M. Kermanian et al., J. Mex. Chem. 57, 290–297 (2013)

    CAS  Google Scholar 

  15. N. Madankumar, K. Pitchumani, Chem. Select 3, 10886–10891 (2018)

    CAS  Google Scholar 

  16. B. Maleki, H. Atharifar, O. Reiser et al., Polycycl. Aromat. Compd. 41, 721–734 (2019)

    Article  Google Scholar 

  17. M.M. Alam, A.T. Mubarak, M.A. Assiri et al., BMC Chem. 13, 1–10 (2019)

    Article  CAS  Google Scholar 

  18. A. Nakhaei, A. Davoodnia, A. Morsali, Res. Chem. Intermed. 41, 7815–7826 (2015)

    Article  CAS  Google Scholar 

  19. A. Davoodnia, A. Zare-Bidaki, H. Behmadi, Chin. J. Catal. 33, 1797–1801 (2012)

    Article  CAS  Google Scholar 

  20. R. Rezaei, R. Khalifeh, M. Rajabzadeh et al., Heterocycl. Comm. 19, 57–63 (2013)

    Article  CAS  Google Scholar 

  21. S.R. Mousavi, H.R. Nodeh, A. Foroumadi, Polycycl. Aromat. Compd. 41, 746–760 (2021)

    Article  CAS  Google Scholar 

  22. M.N. Esfahani, Z. Rafiee, H. Kashi, J. Iran. Chem. Soc. 13, 1449–1461 (2016)

    Article  Google Scholar 

  23. M. Mazloumi, F. Shirini, J. Mol. Struct. 1217, 128326 (2020)

    Article  CAS  Google Scholar 

  24. M. Kiani, M. Mohammadipour, RSC Adv. 7, 997–1007 (2017)

    Article  CAS  ADS  Google Scholar 

  25. A. Khojastehnezhad, M. Rahimizadeh, H. Eshghi et al., Chin. J. Catal. 35, 376–382 (2014)

    Article  CAS  Google Scholar 

  26. U. Kusampally, R. Pagadala, T. Damera et al., Chem. Biodivers. 20, e202300413 (2023)

    Article  CAS  PubMed  Google Scholar 

  27. M.E. Navgire, S.R. Bhitre, A.A. Yelwande et al., Russ. J. Org. Chem. 58, 394–404 (2022)

    Article  CAS  Google Scholar 

  28. M. Sadeghi, A. Ezabadi, B. Omidi et al., Res. Chem. Intermed. 49, 1405–1425 (2023)

    Article  CAS  Google Scholar 

  29. N. Hasannezhad, N. Shadjou, J. Mol. Recognit. 35, e2956 (2022)

    Article  CAS  PubMed  Google Scholar 

  30. F. Mohamadpour, Polycycl. Aromat. Compd. 41, 160–172 (2019)

    Article  Google Scholar 

  31. F. Mohamadpour, Org. Prep. Proced. Int. 52, 64–68 (2020)

    Article  CAS  Google Scholar 

  32. A. Yazdani-Elah-Abadia, M. Maghsoodloua, R. Mohebat et al., Chin. Chem. Lett. 28, 446–452 (2017)

    Article  Google Scholar 

  33. I. Sehout, R. Boulcina, B. Boumoud et al., Synth. Commun. 47, 1185–1191 (2017)

    Article  CAS  Google Scholar 

  34. F. Moeinpour, A. Khojastehnezhad, J. Chem. 9, 504–509 (2012)

    CAS  Google Scholar 

  35. M. Faisal, S. Shahid, S.A. Ghumro et al., Synth. Commun. 48, 462–472 (2018)

    Article  CAS  Google Scholar 

  36. M.G. Dehbalaei, N. Foroughifar, H. Pasdaret et al., New J. Chem. 42, 327–335 (2017)

    Article  Google Scholar 

  37. B. Sardar, R. Jamatia, D. Pal et al., Asian J. Org. Chem. 10, 2195–2204 (2021)

    Article  CAS  Google Scholar 

  38. A. Davoodnia, A. Khojastehnezhad, N. Tavakoli-Hoseini, Bull. Korean Chem. Soc. 32, 2243 (2011)

    Article  CAS  Google Scholar 

  39. A.K. Dutta, P. Gogoi, R. Borah, RSC Adv. 4, 41287–41291 (2014)

    Article  CAS  ADS  Google Scholar 

  40. G. Lavanya, K. Venkatapathy, C.J. Magesh et al., Appl. Organomet. Chem. 33, 1–13 (2019)

    Article  Google Scholar 

  41. S. Yü, S. Wu, X. Zhao et al., Res. Chem. Intermed. 43, 3121–3130 (2017)

    Article  Google Scholar 

  42. X. Fan, Y. Li, X. Zhang et al., Heteroat. Chem. 18, 786–790 (2007)

    Article  CAS  Google Scholar 

  43. N. Sahiba, A. Sethiya, J. Soni et al., J. Mol. Struct. 1268, 133676 (2022)

    Article  CAS  Google Scholar 

  44. Z. Amiri, M. Malmir, T. Hosseinnejad et al., Mol. Catal. 524, 112319 (2022)

    Article  CAS  Google Scholar 

  45. U.M. Mandle, L.A. Dhale, S.B. Godase et al., Ferroelectrics 598, 169–186 (2022)

    Article  CAS  ADS  Google Scholar 

  46. L.N. Nasirmahale, F. Shirini, Y. Bayat et al., New J. Chem. 46, 23129–23138 (2022)

    Article  CAS  Google Scholar 

  47. N. Biswas, D. Srimani, J. Org. Chem. 86, 9733–9743 (2021)

    Article  CAS  PubMed  Google Scholar 

  48. M.A. Zolfigol, N. Bahrami-Nejad, S. Baghery, J. Mol. Liq. 218, 558–564 (2016)

    Article  CAS  Google Scholar 

  49. P. Choudhury, P. Ghosh, B. Basu, Mol. Divers. 24, 283–294 (2020)

    Article  CAS  PubMed  Google Scholar 

  50. J. Kour, M. Gupta, B. Chowhan et al., J. Iran. Chem. Soc. 16, 2587–2612 (2019)

    Article  CAS  Google Scholar 

  51. S. Asgharnasl, R. Eivazzadeh-Keihan, F. Radinekiyan et al., Biol. Macromol. 144, 29–46 (2020)

    Article  CAS  Google Scholar 

  52. G. Shinde, J. Thakur, Res. Chem. Intermed. 50, 817–838 (2023)

    Article  Google Scholar 

Download references

Acknowledgements

The authors gratefully acknowledge the financial support from the Department of Science Technology-Science and Engineering Research Board (DST-SERB) and the University Grants Commission (UGC) as a major research project. One of the authors Nilam Dhane thanks to Bharat Ratna Dr. C. N. Rao Research Laboratory Yashavantrao Chavan Institute of Science, Satara (Autonomous). A Lead College of Karmaveer Bhaurao Patil University, Satara for providing laboratory facilities. And also thankful to Rajarshi Chhatrapati Shahu College, Kolhapur.

Funding

No funding was received to assist with the preparation of this manuscript.

Author information

Authors and Affiliations

  1. Rajarshi Chhatrapati Shahu College, Kolhapur, India

    Nilam S. Dhane, Sanchita M. Dhumal, Ganesh K. Chougule, Samadhan P. Pawar & Kishor V. Gaikwad

  2. Yashavantrao Chavan Institute of Science, Satara, Lead College of Karmaveer Bhaurao Patil University, Satara, India

    Aboli C. Sapkal, Suraj R. Attar & Santosh B. Kamble

Authors
  1. Nilam S. Dhane
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Aboli C. Sapkal
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Suraj R. Attar
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Sanchita M. Dhumal
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Ganesh K. Chougule
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Samadhan P. Pawar
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Santosh B. Kamble
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Kishor V. Gaikwad
    View author publications

    You can also search for this author in PubMed Google Scholar

Contributions

NSD: Conceptualization and collection of information and writing the manuscript, ACS: Collection of Information and Interpretation of the result, SRA: Collection of Information and Interpretation of the result, SM D: Helped to interpret the data, GKC: Helped to interpret the data, SPP: Helped to interpret the data, SBK: Supervision, Design and Implementation of the Research, KVG: Supervision, Design and Implementation of the Research.

Corresponding authors

Correspondence to Santosh B. Kamble or Kishor V. Gaikwad.

Ethics declarations

Conflict of interest

The author' declared that they have no conflict of interest.

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 532 KB)

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Dhane, N.S., Sapkal, A.C., Attar, S.R. et al. Synthesis of 1, 8-dioxodecahydroacridines via Hantzsch condensation using theophylline in an aqueous medium: an eco-friendly and bio-based approach. Res Chem Intermed 50, 1147–1160 (2024). https://doi.org/10.1007/s11164-023-05213-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-023-05213-1

Keywords

Search

Navigation