Skip to main content
Log in

DBU-catalyzed expeditious and facile multicomponent synthesis of N-arylquinolines under microwave irradiation

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

Abstract

N-Arylquinoline derivatives are obtained in excellent yields by a rapid, easy, and efficient one-pot multicomponent reaction of aromatic aldehydes, 3-arylamino-5,5-dimethylcyclohex-2-enone, and active methylene compounds utilizing 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as a catalyst in ethanol under microwave irradiation.

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.

Scheme 1

Similar content being viewed by others

References

  1. Beagley P, Blackie MAL, Chibale K, Clarkson C, Meijboom R, Moss JR, Smith P, Su H (2003) Dalton Trans 3046

  2. Sawada Y, Kayakiri H, Abe Y, Mizutani T, Inamura N, Asano M, Hatori C, Aramori I, Oku T, Tanaka H (2004) J Med Chem 47:2853

    Article  CAS  Google Scholar 

  3. Ma Z, Hano Y, Nomura T, Chen Y (2004) Bioorg Med Chem Lett 14:1193

    Article  CAS  Google Scholar 

  4. Denton TT, Zhang X, Cashman JR (2005) J Med Chem 48:224

    Article  CAS  Google Scholar 

  5. Fokialakis N, Magiatis P, Chinou L, Mitaku S, Tillequin F (2002) Chem Pharm Bull 50:413

    Article  CAS  Google Scholar 

  6. Fossa P, Mosti L, Menozzi G, Marzano C, Baccichetti F, Bordin F (2002) Bioorg Med Chem 10:743

    Article  CAS  Google Scholar 

  7. Ryckebusch A, Derprez-Poulain R, Maes L, Debreu-Fontaine MA, Mouray E, Grellier P, Sergheraert C (2003) J Med Chem 46:542

    Article  CAS  Google Scholar 

  8. Morgan LR, Jursic BS, Hooper CL, Neumann DM, Thangaraj K, Leblanc B (2002) Bioorg Med Chem Lett 12:3407

    Article  CAS  Google Scholar 

  9. Skraup H (1880) Chem Ber 13:2086

    Google Scholar 

  10. Doebner O, Miller VW (1881) Chem Ber 14:2812

    Article  Google Scholar 

  11. Conrad M, Limbach L (1887) Chem Ber 20:944

    Article  Google Scholar 

  12. Combes A (1888) Compt Rend 106:142

    Google Scholar 

  13. Pfitzinger WJ (1886) Prakt Chem 33:100

    Article  Google Scholar 

  14. Demeunynck M, Moucheron C, Mesmaeker AK-D (2002) Tetrahedron Lett 43:261

    Article  CAS  Google Scholar 

  15. Ali MM, Tasneem KC, Rajanna PK, Prakash S (2001) Synlett 251

  16. Palacios F, Ochoa de Retana AM, Oyarzabal J (1999) Tetrahedron 55:5947

    Article  CAS  Google Scholar 

  17. Cho CS, Kim BT, Kim TJ, Shim SC (2001) Chem Commun 2576

  18. Crousse B, Begue J-P, Bonnet-Delpon D (2000) J Org Chem 65:5009

    Article  CAS  Google Scholar 

  19. Hsiao Y, Rivera NR, Yasuda N, Hughes DL, Reider PJ (2001) Org Lett 3:1101

    Article  CAS  Google Scholar 

  20. Assy MG, Abd-Ell Motti FM (1996) Indian J Chem Sect B 35:608

    Google Scholar 

  21. Wang X-S, Zhang M-M, Jiang H, Shi D-Q, Tu S-J (2007) J Chin Chem Soc 54:1033

    CAS  Google Scholar 

  22. Lichitsky BV, Dudinov AA, Krayushkin MM (2001) Arkivoc ix:73

  23. Moseley JD, Kappe CO (2011) Green Chem 13:794

    Article  CAS  Google Scholar 

  24. Caddick S, Fitzmaurice R (2009) Tetrahedron 65:3325

    Article  CAS  Google Scholar 

  25. Ganem B (2009) Acc Chem Res 42:463

    Article  CAS  Google Scholar 

  26. Orru RVA, de Greef M (2003) Synthesis 1471

  27. Wang X-S, Zhang M-M, Jiang H, Yao C-S, Tu S-J (2007) Tetrahedron 63:4439

    Article  CAS  Google Scholar 

  28. Gao S, Tsai CH, Tseng C, Yao C-F (2008) Tetrahedron 64:9143

    Article  CAS  Google Scholar 

  29. Tu S-J, Jiang B, Jia R-H, Zhang J-Y, Zhang Y, Yao C-S, Shi F (2006) Org Biomol Chem 4:3664

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors are thankful to the Department of Biotechnology, New Delhi for financial assistance.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Krishna Nand Singh.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Singh, S.K., Singh, K.N. DBU-catalyzed expeditious and facile multicomponent synthesis of N-arylquinolines under microwave irradiation. Monatsh Chem 143, 805–808 (2012). https://doi.org/10.1007/s00706-011-0651-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-011-0651-y

Keywords

Navigation