Skip to main content
SpringerLink
Log in

Low transition temperature mixtures prompted one-pot synthesis of 5, 10 dihydropyrimido[4,5-b]quinoline-2,4(1H,3H)-dione derivatives

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

Abstract

An efficient green protocol has been investigated for the synthesis of pyrimido[4,5-b]quinolines derivatives via one-pot three-component condensation of 4-chloro aniline, aromatic aldehyde and barbituric acid using low transition temperature mixtures as new generation and sustainable solvents. The process was accomplished with the use of greener and recyclable reaction media, simple methodology, easy workup procedures and no chromatographic purification with high yield. This new approach is expected to discover some significance in combinatorial synthesis of biologically active scaffolds.

Graphical Abstract

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

Similar content being viewed by others

References

  1. R.P. Gore, A.P. Rajput, Drug Discov. Today Technol. 5, 148–152 (2013)

    CAS  Google Scholar 

  2. E. Ruijter, V.A.O. Romano, Drug Discov. Today Technol. 10, 15–20 (2013)

    Article  Google Scholar 

  3. J.E. Biggs-Houck, A. Younai, J.T. Shaw, Curr. Opin. Chem. Biol. 14, 371–382 (2010)

    Article  CAS  Google Scholar 

  4. B. Jiang, T. Rajale, W. Wever, S.J. Tu, G. Li, Chem. Asian J. 5, 2318–2335 (2010)

    Article  CAS  Google Scholar 

  5. S. Damavandi, R. Sandaroos, Chem. Sci. Trans. 1(1), 117–120 (2012)

    Article  CAS  Google Scholar 

  6. M. Haji, Beilstein J. Org. Chem. 12, 1269–1301 (2016)

    Article  CAS  Google Scholar 

  7. J.D. Sunderhaus, S.F. Martin, Chemistry 15(6), 1300–1308 (2009)

    Article  CAS  Google Scholar 

  8. Y. Gu, Green Chem. 14, 2091–2128 (2012)

    Article  CAS  Google Scholar 

  9. A.A. Otaibi, A. McCluskey, Ionic liquids: new aspects for the future http://dx.doi.org/10.5772/51937

  10. A. Dömling, W. Wang, K. Wang, Chem. Rev. 112, 3083–3135 (2012)

    Article  Google Scholar 

  11. P.T. Anastas, J.C. Warner, Green chemistry: theory and practice (Oxford University Press, New York, 1998), p. 30

    Google Scholar 

  12. A.P. Abbott, G. Capper, D.L. Davies, R.K. Rasheed, V. Tambyrajah, Chem. Commun. 1, 70–71 (2003)

    Article  Google Scholar 

  13. M. Francisco, A. Bruinhorst, M.C. Kroon, Angew. Chem. Int. Ed. 52, 3074–3085 (2013)

    Article  CAS  Google Scholar 

  14. C.L. Yiin, A.T. Quitain, S. Yusup, M. Sasaki, Y. Uemura, T. Kida, Bioresour. Technol. 199, 258–264 (2016)

    Article  CAS  Google Scholar 

  15. L.F. Zubeir, M.H.M. Lacroix, M.C. Kroon, J. Phys. Chem. B 118, 14429−14441 (2014)

    Article  CAS  Google Scholar 

  16. X. Li, M. Hou, B. Han, X. Wang, L. Zou, J. Chem. Eng. Data 53, 548–550 (2008)

    Article  CAS  Google Scholar 

  17. A.P. Abbott, E.I. Ahmed, R.C. Harris, K.S. Ryder, Green Chem. 16, 4156–4161 (2014)

    Article  CAS  Google Scholar 

  18. Q. Zeng, Y. Wang, Y. Huang, X. Ding, J. Chen, K. Xu, Analyst 139, 2565–2573 (2014)

    Article  CAS  Google Scholar 

  19. E. Su, A.M. Klibanov, Appl. Biochem. Biotechnol. 177, 753–758 (2015)

    Article  CAS  Google Scholar 

  20. G. Imperato, S. Hoger, D. Lenoir, B. Konig, Green Chem. 8, 1051–1055 (2006)

    Article  CAS  Google Scholar 

  21. S.B. Phadtare, G.S. Shankarling, Green Chem. 12, 458–462 (2010)

    Article  CAS  Google Scholar 

  22. J.G. Álvarez, C. Vidal, Eur. J. Inorg. Chem. 31, 5147–5157 (2015)

    Article  Google Scholar 

  23. F. Ilgen, B. Konig, Green Chem. 11, 848–854 (2009)

    Article  CAS  Google Scholar 

  24. P. Liu, J.W. Hao, L.P. Mo, Z.H. Zhang, RSC Adv. 5, 48675–48704 (2015)

    Article  CAS  Google Scholar 

  25. S. Khandelwal, Y.K. Tailor, M. Kumar, J. Mol. Liq. 215, 345–386 (2016)

    Article  CAS  Google Scholar 

  26. U.N. Yadav, G.S. Shankarling, J. Mol. Liq. 191, 137–141 (2014)

    Article  CAS  Google Scholar 

  27. D.R. Chandam, A.G. Mulik, D.R. Patil, A.P. Patravale, D.R. Kumbhar, M.B. Deshmukh, J. Mol. Liq. 219, 573–578 (2016)

    Article  CAS  Google Scholar 

  28. N. Azizi, S. Dezfooli, M. Khajeh, M.M. Hashemi, J. Mol. Liq. 186, 76–80 (2013)

    Article  CAS  Google Scholar 

  29. M.B. Hole, N.S. Dighe, S.R. Pattan, D.S. Musmade, V.M. Gawarel, S.S. Dengale, S.R. Butle, Pharmacologyonline 1, 200–207 (2010)

    Google Scholar 

  30. M.M. Ghorab, F.A. Ragab, H.I. Heiba, W.M. Ghorabc, J. Heterocycl. Chem. 48, 1269–1279 (2011)

    Article  CAS  Google Scholar 

  31. A.B.A. El-Gazzar, M.M. Youssef, A.M.S. Youssef, A.A. Abu-Hashem, F.A. Badria, Eur. J. Med. Chem. 44, 609–624 (2009)

    Article  CAS  Google Scholar 

  32. J. Azizian, A.S. Delbari, K. Yadollahzadeh, Synth. Commun. 44, 3277–3286 (2014)

    Article  CAS  Google Scholar 

  33. S. Dudkin, V.O. Iaroshenko, V.Y. Sosnovskikh, A.A. Tolmachev, A. Villingera, P. Langer, Org. Biomol. Chem. 11, 5351–5361 (2013)

    Article  CAS  Google Scholar 

  34. J. Trilleras, L.G. López, D.J. Pacheco, J. Quiroga, M. Nogueras, J.M. de la Torre, J. Cobo, Molecules 15, 7227–7234 (2010)

    Article  CAS  Google Scholar 

  35. J. Quiroga, J. Trilleras, B. Insuasty, R. Abonía, M. Nogueras, A. Marchal, J. Cobo, Tetrahedron Lett. 51, 1107–1109 (2010)

    Article  CAS  Google Scholar 

  36. E.M.E. Fatma, I.A. Shatha, A.E. Ola, M.A. Hassan, J. King Saud. Univ. Sci. 18(1), 1–17 (2005)

    Google Scholar 

  37. S. Damavandi, R. Sandaroos, Chem. Sci. Trans. 1(1), 117–120 (2012)

    Article  CAS  Google Scholar 

  38. B.S. Rane, S.V. Deshmukh, M.G. Ghagare, R.V. Rote, M.N. Jachak, J. Chem. Pharm. Res. 4(7), 3562–3567 (2012)

    CAS  Google Scholar 

  39. K. Tabatabaeian, A.F. Shojaei, F. Shirini, S.Z. Hejazi, M. Rassa, Chin. Chem. Lett. 25, 308–312 (2014)

    Article  CAS  Google Scholar 

  40. D.Q. Shi, S.N. Ni, F. Yang, J.W. Shi, G.L. Dou, X.Y. Li, X.S. Wang, S.J. Ji, J. Heterocycl. Chem. 45, 693–702 (2008)

    Article  CAS  Google Scholar 

  41. D.Q. Shi, L.H. Niu, H. Yao, H. Jiangc, J. Heterocycl. Chem. 46, 237–242 (2009)

    Article  CAS  Google Scholar 

  42. A.K. Nezhad, S. Sarikhani, E.S. Shahidzadeh, F. Panahi, Green Chem. 14, 2876–2884 (2012)

    Article  Google Scholar 

  43. M. Sankaran, C. Kumarasamy, U. Chokkalingam, P.S. Mohan, Bioorg. Med. Chem. Lett. 20, 7147–7151 (2010)

    Article  CAS  Google Scholar 

  44. K. Aknin, S. Desbène-Finck, P. Helissey, S. Giorgi-Renault, Mol. Divers. 14, 123–130 (2010)

    Article  CAS  Google Scholar 

  45. S.J. Jadhav, R.B. Patil, D.R. Kumbhar, A.A. Patravale, D.R. Chandam, M.B. Deshmukh, Res. Chem. Intermed. 43, 2529–2543 (2017)

    Article  CAS  Google Scholar 

  46. A.A. Patravale, A.H. Gore, D.R. Patil, G.B. Kolekar, M.B. Deshmukh, P.B. Choudhari, M.S. Bhatia, P.V. Anbhule, Res. Chem. Intermed. 42, 2919 (2016)

    Article  CAS  Google Scholar 

  47. P.P. Warekar, P.T. Patil, K.T. Patil, D.K. Jamale, G.B. Kolekar, Prashant V. Anbhule, Res. Chem. Intermed. (2017). doi:10.1007/s11164-017-2865-z

    Google Scholar 

  48. D.R. Chandam, A.G. Mulik, P.P. Patil, S.D. Jagdale, D.R. Patil, S.A. Sankpal, M.B. Deshmukh, J. Mol. Liq. 207, 14–20 (2015)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors thank the Department of Science and Technology New Delhi, Govt. of India, for the award of an INSPIRE fellowship (JRF) for financial support. We gratefully acknowledge the Department of Chemistry, Shivaji University, Kolhapur, for providing NMR spectral analysis.

Author information

Authors and Affiliations

  1. Chemistry Research Laboratory, Department of Agrochemicals and Pest Management, Shivaji University, Kolhapur, Maharashtra, 416004, India

    Priyanka P. Mohire, Reshma B. Patil, Sunetra J. Jadhav, Digambar R. Kumbhar, Jai S. Ghosh & Madhukar B. Deshmukh

  2. Heterocyclic Chemistry Laboratory, Department of Chemistry, Shivaji University, Kolhapur, Maharashtra, 416004, India

    Dattatraya R. Chandam, Ajinkya A. Patravale & Madhukar B. Deshmukh

  3. Department of Chemistry, Vivekanand College, Kolhapur, Maharashtra, 416004, India

    Ajinkya A. Patravale

Authors
  1. Priyanka P. Mohire
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Reshma B. Patil
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Dattatraya R. Chandam
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Sunetra J. Jadhav
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Ajinkya A. Patravale
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Digambar R. Kumbhar
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Jai S. Ghosh
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Madhukar B. Deshmukh
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Madhukar B. Deshmukh.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 3226 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Mohire, P.P., Patil, R.B., Chandam, D.R. et al. Low transition temperature mixtures prompted one-pot synthesis of 5, 10 dihydropyrimido[4,5-b]quinoline-2,4(1H,3H)-dione derivatives. Res Chem Intermed 43, 7013–7028 (2017). https://doi.org/10.1007/s11164-017-3033-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-017-3033-1

Keywords

Search

Navigation