Skip to main content
Log in

Nafion-H®-catalyzed synthesis of polyhydroquinolines via the Hantzsch multicomponent reaction

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

A facile and efficient one-pot, four-component synthesis of polyhydroquinoline derivatives via the Hantzsch reaction using Nafion-H® as heterogeneous catalyst in PEG 400–water solvent system is described herein. The present methodology offers several advantages such as excellent yields, simple procedure, shorter reaction times, and milder conditions with remarkable recyclability.

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.

Fig. 1
Fig. 2
Scheme 1
Scheme 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Guillena G, Ramon DJ, Yus M (2007) Tetrahedron Asymmetry 18:693

    Article  CAS  Google Scholar 

  2. Domling A (2006) Chem Rev 106:17

    Article  Google Scholar 

  3. Simon C, Constantieux T, Rodrigeuz J (2004) Eur J Org Chem 4957

  4. Domling A, Ugi I (2000) Angew Chem Int Ed 39:3168

    Article  CAS  Google Scholar 

  5. Ramon DJ, Yus M (2005) Angew Chem Int Ed 44:1602

    Article  CAS  Google Scholar 

  6. Mauzerall D, Westheimer FH (1955) J Am Chem Soc 77:2261

    Article  CAS  Google Scholar 

  7. Baraldi PG, Budriesi R, Cacciari B, Chiarini A, Garuti L, Giovanninetti G, Leoni A, Roberti M (1992) Collect Czech Chem Commun 57:169

    Article  CAS  Google Scholar 

  8. Di Stilo A, Visentin S, Cena C, Gasco AM, Ermondi G, Gasco A (1998) J Med Chem 41:5393

    Article  Google Scholar 

  9. Kawase M, Shah A, Gaveriya H, Motohashi N, Sakagami H, Varga A, Molnar J (2002) Bioorg Med Chem 10:1051

    Article  CAS  Google Scholar 

  10. Suarez M, Verdecia Y, Illescas B, Martinez-Alvarez R, Alvarez A, Ochoa E, Seoane C, Kayali N, Martin N (2003) Tetrahedron 59:9179

    Article  CAS  Google Scholar 

  11. Shan R, Velazquez C, Knaus EE (2004) J Med Chem 47:254

    Article  CAS  Google Scholar 

  12. Bossert F, Meyer H, Wehinger E (1981) Angew Chem Int Ed 20:762

    Article  Google Scholar 

  13. Takenaka T, Usuda S, Nomura T, Maeno H, Sado T (1976) Arzneim Forsch 26:2172

    CAS  Google Scholar 

  14. Julius S (1988) J Cardiovasc Pharmacol 12:S27

    Article  Google Scholar 

  15. Liang J-C, Yeh J-L, Wang C-S, Liou S-F, Tsai C-H, Chen I-J (2002) Bioorg Med Chem 10:719

    Article  CAS  Google Scholar 

  16. Boschi D, Caron G, Visentin S, Di Stilo A, Rolando B, Fruttero R, Gasco A (2001) Pharm Res 18:987

    Article  CAS  Google Scholar 

  17. Godfraind T, Miller R, Wibo M (1986) Pharmacol Rev 38:321

    CAS  Google Scholar 

  18. Fleckenstein-Gruen G, Thimm F, Czirfuzs A, Matyas S, Frey M (1994) J Cardiovasc Pharmacol 24:75

    Google Scholar 

  19. Manpadi M, Uglinskii PY, Rastogi SK, Cotter KM, Wong Y-SC, Anderson LA, Ortega AJ, Van Slambrouck S, Steelant WFA, Rogelj S, Tongwa P, Antipin MY, Magedov IV, Kornienko A (2007) Org Biomol Chem 5:3865

    Article  CAS  Google Scholar 

  20. Emanuel NM, Obukhova LK, Dubur GJ, Tirzit GD, Uldrikis JR (1985) Dokl Akad Nauk SSSR 284:1271

    CAS  Google Scholar 

  21. Bird GLA, Prach AT, McMahon AD, Forrest JAH, Mills PR, Danesh BJ (1998) J Hepatol 28:194

    Article  CAS  Google Scholar 

  22. Ogawa AK, Willoughby CA, Bergeron R, Ellsworth KP, Geissler WM, Myers RW, Yao J, Harris G, Chapman KT (2003) Bioorg Med Chem Lett 13:3405

    Article  CAS  Google Scholar 

  23. Klusa V (1995) Drugs Future 20:135

    Google Scholar 

  24. Bretzol RG, Bollen CC, Maester E, Federlin KF (1993) Am J Kidney Dis 21:53

    Google Scholar 

  25. Bretzel RG, Bollen CC, Maeser E, Federlin KF (1992) Drugs Future 17:465

    Google Scholar 

  26. Boer R, Gekeler V (1995) Drugs Future 20:499

    Google Scholar 

  27. Eisner U, Kuthan J (1972) Chem Rev 72:1

    Article  CAS  Google Scholar 

  28. Stout DM, Meyers AI (1982) Chem Rev 82:223

    Article  CAS  Google Scholar 

  29. Kutney JP (1977) Heterocycles 7:593

    Article  CAS  Google Scholar 

  30. Widdowson DA (1978) In: Van Tamelen EE (ed) Bioorganic chemistry, Series 4. Academic, New York, p 239

    Google Scholar 

  31. Hantzsch A (1882) Justus Liebigs Ann Chem 215:1

    Article  Google Scholar 

  32. Loev B, Snader KM (1965) J Org Chem 30:1914

    Article  CAS  Google Scholar 

  33. Tu S-J, Zhou J-F, Deng X, Cai P-J, Wan H, Feng J-C (2001) Chin J Org Chem 21:313

    CAS  Google Scholar 

  34. Sabitha G, Reddy GSKK, Reddy CS, Yadav JS (2003) Tetrahedron Lett 44:4129

    Article  CAS  Google Scholar 

  35. Ji S-J, Jiang Z-Q, Lu J, Loh T-P (2004) Synlett 5:831

    Article  Google Scholar 

  36. Breitenbucher JG, Figliozzi G (2000) Tetrahedron Lett 41:4311

    Article  CAS  Google Scholar 

  37. Dondoni A, Massi A, Minghini E, Bertolasi V (2004) Tetrahedron 60:2311

    Article  CAS  Google Scholar 

  38. Ko S, Sastry MNV, Lin C, Yao C-F (2005) Tetrahedron Lett 46:5771

    Article  CAS  Google Scholar 

  39. Ko S, Yao C-F (2006) Tetrahedron 62:7293

    Article  CAS  Google Scholar 

  40. Wang L-M, Sheng J, Zhang L, Han J-W, Fan Z-Y, Tian H, Qian C-T (2005) Tetrahedron 61:1539

    Article  CAS  Google Scholar 

  41. Maheswara M, Siddaiah V, Damu GLV, Rao CV (2006) Arkivoc 2:201

    Google Scholar 

  42. Heravi MM, Bakhtiari K, Javadi NM, Bamoharram FF, Saeedi M, Oskooie HA (2007) J Mol Catal A Chem 264:50

    Article  CAS  Google Scholar 

  43. Nagarapu L, Kumari MD, Kumari NV, Kantevari S (2007) Catal Commun 8:1871

    Article  CAS  Google Scholar 

  44. Olah GA, Iyer PS, Prakash GKS (1986) Synthesis 513

  45. Olah GA, Prakash GKS, Sommer J (1985) Superacids. Wiley Interscience, New York

    Google Scholar 

  46. Arata K (1990) Adv Catal 37:165

    Article  CAS  Google Scholar 

  47. Yeo SC, Eisenberg A (1977) J Appl Polym Sci 21:875

    Article  CAS  Google Scholar 

  48. Yeager HL, Eisenberg A (1982) In: Eisenberg A, Yeager HL (eds), Perflourinated ionomer membranes. ACS Symposium series, vol. 180, American Chemical Society, Washington, DC, p 1

  49. Polshettiwar V, Varma RS (2008) Acc Chem Res 41:629

    Article  CAS  Google Scholar 

  50. Polshettiwar V, Varma RS (2008) Chem Soc Rev 37:1546

    Article  CAS  Google Scholar 

  51. Anastas PT, Warner JC (1998) Green chemistry: theory and practice. Oxford University Press, Oxford

    Google Scholar 

  52. Chen J, Spear SK, Huddleston JG, Rogers RD (2005) Green Chem 7:64

    Article  CAS  Google Scholar 

  53. Zhang Z-H, Yin L, Wang Y-M, Liu J-Y, Li Y (2004) Green Chem 6:563

    Article  CAS  Google Scholar 

  54. Kumar R, Chaudhary P, Nimesh S, Chandra R (2006) Green Chem 8:356

    Article  CAS  Google Scholar 

  55. Winter A, van den Berg AMJ, Hoogenboom R, Kickelbick G, Schubert US (2006) Synthesis 2873

  56. Han W, Liu C, Jin Z-L (2007) Org Lett 9:4005

    Article  CAS  Google Scholar 

  57. Smith CB, Raston CL, Sobolev AN (2005) Green Chem 7:650

    Article  CAS  Google Scholar 

  58. Kidwai M, Bhatnagar D, Chauhan R (2011) J Heterocycl Chem. doi:10.1002/jhet.1037

  59. Kidwai M, Chauhan R, Bhatnagar D (2011) J Sulfur Chem 32:37

    Article  CAS  Google Scholar 

  60. Seen AJ (2001) J Mol Catal A Chem 177:105

    Article  CAS  Google Scholar 

  61. Kumar S, Sharma P, Kapoor KK, Hundal MS (2008) Tetrahedron 64:536

    Article  CAS  Google Scholar 

  62. Mobinikhaledi A, Foroughifar N, Fard MAB, Moghanian H, Ebrahimi S, Kalhor M (2009) Synth Commun 39:1166

    Article  CAS  Google Scholar 

  63. Bandgar BP, More PE, Kamble VT, Totre JV (2008) Arkivoc 15:1

    Google Scholar 

  64. Lingaiah BV, Ezikiel G, Yakaiah T, Reddy GV, Rao PS (2006) Synlett 15:2507

    Google Scholar 

  65. Zhu D, Chen J, Xiao H, Liu M, Ding J, Wu H (2009) Synth Commun 39:2895

    Article  CAS  Google Scholar 

  66. Sheldrick GM (1997) SHELXL 97, A program for the determination of crystal structure. Anorganisch-Chemisches Institut der Universität Göttingen, Germany

  67. Cromer DT, Mann JB (1968) Acta Cryst A24:321

    Google Scholar 

  68. Stewart RF, Davidson ER, Simpson WT (1965) J Chem Phys 42:3175

    Article  CAS  Google Scholar 

Download references

Acknowledgments

Ritika Chauhan is grateful to UGC (University Grants Commission) for providing junior research fellowship. We express our thanks to the Director of University Science and Instrumentation Centre, University of Delhi, Delhi, for providing the spectral data and also acknowledge the Head of the Biophysics Department, All India Institute of Medical Sciences, New Delhi, for carrying out the X-ray studies.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Mazaahir Kidwai.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 83 kb)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kidwai, M., Chauhan, R., Bhatnagar, D. et al. Nafion-H®-catalyzed synthesis of polyhydroquinolines via the Hantzsch multicomponent reaction. Monatsh Chem 143, 1675–1680 (2012). https://doi.org/10.1007/s00706-012-0742-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-012-0742-4

Keywords

Navigation