Skip to main content

Advertisement

Log in

Sulfamic acid-catalyzed multicomponent synthesis of 7-phenyl-7,12 dihydrobenzo(h)pyrido[2,3-b]naphthydrin-6(5H)-one derivatives: a green avenue

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

Abstract

A series of novel 7-phenyl-7,12-dihydrobenzo(h)pyrido[2,3-b]naphthydrin-6(5H)-one were synthesized by a one-pot three-component condensation of 2,4-dihydroxyquinoline, 2-amino pyridine and various aromatic aldehydes with sulfamic acid as an enviro-economic catalyst. The salient features of this method consist of high atom economy and yields, short reaction time, non-carcinogenic solvents, and chromatography-free work-up procedure. Fascinatingly, the catalyst can be reused for up to four cycles giving good to excellent yields. By employing this method, a series of 14 pyrido[2,3-b]naphthydrin compounds were synthesized. This procedure is projected as a green avenue in the combinatorial synthesis of biologically active naphthydrin derivatives.

Graphical Abstract

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

Fig. 1
Scheme1
Fig. 2
Scheme 2
Fig. 3

Similar content being viewed by others

References

  1. E. Ruijter, R. Scheffelaar, R.V.A. Orru, Angew. Chem. Int. Ed. 50, 6234 (2011)

    Article  CAS  Google Scholar 

  2. A. Maleki, Tetrahedron 68, 7827 (2012)

    Article  CAS  Google Scholar 

  3. V.A. Orru Romamo, E. Ruijter, Synthesis of Heterocycles via Multicomponent Reactions II (Springer, New York, 2010), pp. 28–93

    Google Scholar 

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

    Article  Google Scholar 

  5. C.J. Li, Chem. Rev. 105, 3095 (2005)

    Article  CAS  Google Scholar 

  6. A. Maleki, R. Rahimi, S. Maleki, N. Hamidi RSC Adv. 4, 29765 (2014)

    Article  CAS  Google Scholar 

  7. A. Maleki, Z. Alirezvani, S. Maleki, Catal. Commun. doi: 10.1016/j.catcom.2015.05.014

  8. A. Maleki, A. Sarvary, RSC Adv. 5, 60938 (2015)

    Article  CAS  Google Scholar 

  9. A. Maleki, M. Aghaei, N. Ghamari, Chem. Lett. 44, 259 (2015)

    Article  CAS  Google Scholar 

  10. S.P. Rajendran, N. Sampathkumar, G.A. Prakash, Asian J. Chem. 14, 1303 (2002)

    Google Scholar 

  11. S.P. Rajendran, G.A. Prakash, Asian J. Chem. 15, 500 (2003)

    Google Scholar 

  12. S.P. Rajendran, G.A. Prakash, Oriental. J. Chem. 19, 173 (2003)

    Google Scholar 

  13. P.M. Gilis, A. Haemers, W. Bollaert, J. Heterocycl. Chem. 17, 717 (1980)

    Article  CAS  Google Scholar 

  14. A. Marchese, E.A. Debbia, G.C. Schito, J. Antimicrobial Chemother. 46, 11 (2000)

    Article  CAS  Google Scholar 

  15. A.M.F. Elgohary, E.M. Ezz El-Arab, J. Chem. 1, 1 (2013)

    Google Scholar 

  16. A.M. Bothaina, H.B. Ashraf, M.K. Makarem, G.A. Mohamed, A.E. Samar, Int. J. Org. Chem. 5, 37 (2015)

    Article  Google Scholar 

  17. G.B. Balin, W.L. Tan, Aus. L. Chem. 37, 1065 (1984)

    Article  Google Scholar 

  18. D. Chiara, C. Massimo, G. Maogheri, D.B. Mario, R. Giorgio, F. Robert, Int. J. Inflam. 34, 1 (2006)

    Google Scholar 

  19. T. Kuroda, F. Suzuki, T. Tamura, K. Ohmori, H. Hose, J. Med. Chem. 35, 1130 (1992)

    Article  CAS  Google Scholar 

  20. S.C. Kuo, S.Y. Tsai, H.T. Li, C.H. Wu, K. Ishii, H. Nakamura, Chem. Pharm. Bull. 36, 4403 (1988)

    Article  CAS  Google Scholar 

  21. M.Q. Jose, P. Carlos, G. Liliana, I. Raul, Eur. J. Med. Chem. 38, 265 (2003)

    Article  Google Scholar 

  22. P.S. Hameed, A. Raichurkar, P. Madhavapeddi, S. Menasinakai, S. Sharma, P. Kaur, R. Nandishaiah, V. Panduga, J. Reddy, V.K. Sambandamurthy, D. Sriram, Med. Chem. Lett. 5, 820 (2014)

    Article  Google Scholar 

  23. O. Di Pietro, F.J. Perez-Areales, J. Juarez-Jimenez, A. Espargaro, M.V. Clos, B. Perez, R. Lavilla, R. Sabate, F.J. Luque, D. Munoz-Torrero, Eur. J. Med. Chem. 84, 107 (2014)

    Article  Google Scholar 

  24. K.L. Jansen, R. Heirbaut, J.D. Verkerk, J. Cheng, P. Joossens, L. Cos, A.M. Maes, I.D. Lambeir, K. Meester, Augustyns, P.V. der Veken, J. Med. Chem 57, 3053 (2014)

    Article  CAS  Google Scholar 

  25. X.Z. Zhao, S.J. Smith, M. Metifiot, B.C. Johnson, C. Marchand, Y. Pommier, S.H. Hughes, T.R. Burke, J. Med. Chem. 57, 1573 (2014)

    Article  CAS  Google Scholar 

  26. K.H. Kim, A. Wissner, J.R.M.B. Floyed, H.L. Fraser, Y.D. Wang, R.G. Dusin, Y. Hu, A. Olland, B. Guo, K. Arndt, Biorg. Med. Chem. Lett. 19, 5225 (2009)

    Article  CAS  Google Scholar 

  27. S.U. Lee, J.H. Park, J.Y. Lee, C.G. Shin, B.Y. Chug, Y.S. Lee, Bull. Korean Chem. Soc. 27, 1888 (2006)

    Article  CAS  Google Scholar 

  28. G. Giacomello, F. Gualteri, F.M. Ricceri, M.L. Stein, Tetrahedron Lett. 6(16), 1117 (1965)

    Article  Google Scholar 

  29. R. Tan, A. Taurins, Tetrahedron Lett. 6(31), 2737 (1965)

    Article  Google Scholar 

  30. D. Bouzard, P. Di Cesare, M. Essiz, J.P. Jacquet, B. Ledoussal, P. Remuzon, R.E. Kessler, T.J. Fung, J. Med. Chem. 35, 518 (1992)

    Article  CAS  Google Scholar 

  31. H. Helmut, P. Juergen, Z. Hans, W. Bruno, K.W. Otto, Chem. Abstr. 114, 122342 (1990)

    Google Scholar 

  32. S.S. May, E. Mohamed, M. Rahim, Der Chem. Sin. 2/1, 66 (2011)

    Google Scholar 

  33. A.M. Hayallah, M.K. Abdel-Hamid, Der Pharma Chem. 6/5, 45 (2014)

    Google Scholar 

  34. I.N. Bardasov, A.U. Alekseeva, O.V. Ershov, M.Y. Belikov, Tetrahedron Lett. 56, 5434 (2015)

    Article  CAS  Google Scholar 

  35. J.F. Wu, M.M. Liu, S.X. Huang, Y. Wang, Bioorg. Med. Chem. Lett. 25, 3251 (2015)

    Article  CAS  Google Scholar 

  36. D.J. Brown, E.C. Taylor, P. Wipf, A. Weissberger, The Chemistry of Heterocyclic Compounds, vol. 63, (Wiley, 2008), p. 1

  37. W.M. Kana, M.M. Rosenman, K. Sakurai, T.M. Snyder, D.R. Liu, Nature 431, 545 (2004)

    Article  Google Scholar 

  38. A. Maleki, Tetrahedron Lett. 54, 2055 (2013)

    Article  CAS  Google Scholar 

  39. A. Maleki, A. Sarvary, Mol.Divers. 19, 189 (2015)

    Article  Google Scholar 

  40. B. Ganem, Acc. Chem. Res. 42, 463 (2009)

    Article  CAS  Google Scholar 

  41. A. Domling, Chem. Rev. 106, 17 (2006)

    Article  Google Scholar 

  42. A. Maleki, RSC Adv. 4, 64169 (2014)

    Article  CAS  Google Scholar 

  43. A. Maleki, E. Akhlaghi, R. Paydar, Appl. Organometal. Chem. 30, 382 (2016)

    Article  CAS  Google Scholar 

  44. G. Brahmachari, B. Banerjee, A.C.S. Sustain, Chem. Eng. 2, 2802 (2014)

    CAS  Google Scholar 

  45. G. Brahmachari, A.C.S. Sustainable, Chem. Eng. 3, 2058 (2015)

    CAS  Google Scholar 

  46. P. Rezaee, J. Davarpanah, Res Chem Intermed 42, 6815 (2016)

    Article  CAS  Google Scholar 

  47. A. Kamal, K.S. Babu, S.M. Ali Hussaini, P.S. Srikanth, M. Balakrishna, A. Alarifi, Tetrahedron Lett. 56, 4619 (2015)

    Article  CAS  Google Scholar 

  48. M. Kidwai, R. Chauhan, RSC Adv. 2, 7660 (2012)

    Article  CAS  Google Scholar 

  49. A. Kamal, K.S. Babu, Y. Poornachandra, B. Nagaraju, S.M. Ali Hussaini, S.P. Shaik, C.G. Kumar, A. Alarifi, Arab. J. Chem (2015). doi:10.1016/j.arabjc.2015.10.013

  50. D.R. Patil, D.R. Chandam, A.G. Mulik, P.P. Patil, S. Jagdale, M.B. Deshmukh, Indian J. Chem. 54B, 545 (2015)

    CAS  Google Scholar 

  51. D.R. Chandam, A.G. Mulik, D.R. Patil, A.A. Patravale, D.K. Kumbhar, M.B. Deshmukh, J. Mol. Liq. 219, 573 (2016)

    Article  CAS  Google Scholar 

  52. 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 

  53. S.S. Undere, A.A. Patravale, N.J. Valekar, L.S. Walekar, D.K. Jamale, S. Vibhute, G.B. Kolekar, M.B. Deshmukh, P.V. Anbhule, Res. Chem. Intermed. 42, 4373 (2016)

    Article  Google Scholar 

  54. D.K. Kumbhar, R.B. Patil, D.R. Patil, A.A. Patravale, D.R. Chandam, S.J. Jadhav, M.B. Deshmukh, Synth. Comm. 46, 85 (2016)

    Article  CAS  Google Scholar 

  55. A.A. Patravale, A.H. Gore, D.R. Patil, G.B. Kolekar, M.B. Deshmukh, P.V. Anbhule, Ind. Eng. Chem. Res. 53, 16568 (2014)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We are grateful to the Department of Agrochemical and Pest Management and Department of Chemistry, Shivaji University, Kolhapur, for providing spectral analysis. One of the authors, Prof. M. B. Deshmukh, thanks UGC-New Delhi for the award of a UGC-BSR faculty fellowship.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Madhukar B. Deshmukh.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 183405 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Jadhav, S.J., Patil, R.B., Kumbhar, D.R. et al. Sulfamic acid-catalyzed multicomponent synthesis of 7-phenyl-7,12 dihydrobenzo(h)pyrido[2,3-b]naphthydrin-6(5H)-one derivatives: a green avenue. Res Chem Intermed 43, 2529–2543 (2017). https://doi.org/10.1007/s11164-016-2778-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-016-2778-2

Keywords

Navigation