Catalysis Letters

, Volume 146, Issue 8, pp 1341–1347 | Cite as

NiO Nanoparticles: Efficient Catalyst for Four Component Coupling Reaction for Synthesis of Substituted Pyrroles



The present protocol demonstrates the four component, coupling reactions of 1,3-dicarbonyl compounds, amines, aldehydes, and nitroalkanes for the synthesis of highly functionalized pyrroles using NiO NPs as a heterogeneous and robust catalyst. The developed protocol is simple, convenient, solvent free, straightforward, easy separation of catalyst and carried at room temperature. This methodology provides an alternative approach for easy access of highly substituted pyrroles in moderate to very good yields using four simple and readily available building blocks via one-pot tandem reaction with catalyst recyclability.

Graphical Abstract


NiO NPs Multicomponent Solvent free Coupling reaction 



Author Aravind L. Gajengi thankful to the University Grand Commission–Basic Research Program (UGC-BSR) for providing fellowship. We are also thankful to Department of Science and Technology (DST), India for financial support under DST-Nano Mission Project No. SR/NM/NS-1097/2011.

Supplementary material

10562_2016_1762_MOESM1_ESM.docx (2.2 mb)
Supplementary material 1 (DOCX 2287 kb)


  1. 1.
    Domling A (2006) Chem Rev 106:17CrossRefGoogle Scholar
  2. 2.
    Lehuede J, Fauconneau B, Barrier L, Qurakow M, Piriou A, Vierfond JM (1999) Eur J Med Chem 34:991CrossRefGoogle Scholar
  3. 3.
    Williamson NR, Simonsen HT, Ahmed RAA, Goldet G, Slater H, Woodley L, Leeper FJ, Salmond PC (2005) Mol Microbiol 56:971CrossRefGoogle Scholar
  4. 4.
    Toja E, Selva D, Schiatti P (1984) J Med Chem 27:610CrossRefGoogle Scholar
  5. 5.
    Poeta MD, Schell WA, Dykstra CC, Jones S, Tidwell RR, Czarny A, Bajic M, Kumar A, Boykin D, Perfect JR (1998) Antimicrob Agents Chemother 42:2495Google Scholar
  6. 6.
    Biava M, Porretta GC, Deidda D, Pompei R, Tafi A, Manetti F (2004) Bioorg. Med Chem 12:1453CrossRefGoogle Scholar
  7. 7.
    Denny WA, Rewcastle GW, Baguley BC (1990) J Med Chem 33:814CrossRefGoogle Scholar
  8. 8.
    Higgins SJ (1997) Chem Soc Rev 26:247CrossRefGoogle Scholar
  9. 9.
    Kaupp G, Schmeyers J, Kuse A, Atfeh A (1999) Angew Chem Int Ed 38:2896CrossRefGoogle Scholar
  10. 10.
    Kleinspehn GG (1955) J Am Chem Soc 77:1546CrossRefGoogle Scholar
  11. 11.
    Minetto G, Raveglia LF, Sega A, Taddei M (2005) Eur J Org Chem 24:5277CrossRefGoogle Scholar
  12. 12.
    Goyal S, Patel JK, Gangar M, Kumar K, Nair VA (2015) RSC Adv 5:3187CrossRefGoogle Scholar
  13. 13.
    Meshram HM, Babu BM, Kumar GS, Thakur PB, Bangade VM (2013) Tetrahedron Lett 54:2296CrossRefGoogle Scholar
  14. 14.
    Silveira CC, Mendes SR, Martins GM, Schlosser SC, Kaufman TS (2013) Tetrahedron 69:9076CrossRefGoogle Scholar
  15. 15.
    Estevez V, Villacampa M, Menendez JC (2013) Chem Commun 49:591CrossRefGoogle Scholar
  16. 16.
    Maiti S, Biswas S, Jana U (2010) J Org Chem 75:1674CrossRefGoogle Scholar
  17. 17.
    Sarkar S, Bera K, Maiti S, Biswas S, Jana U (2013) Synth Commun 43:1563CrossRefGoogle Scholar
  18. 18.
    Li L, Zhao MN, Ren ZH, Li J, Guan ZH (2012) Synthesis 44:532Google Scholar
  19. 19.
    Khan AT, Lal M, Bagdi PR, Basha RS, Saravanan P, Patra S (2012) Tetrahedron Lett 53:4145CrossRefGoogle Scholar
  20. 20.
    Li BL, Zhang M, Hu HC, Du X, Zhang ZH (2014) N J Chem 38:2435CrossRefGoogle Scholar
  21. 21.
    Tang J, Yang M, Yang M, Wang J, Dong W, Wang G (2015) N J Chem 39:4919CrossRefGoogle Scholar
  22. 22.
    Li BL, Hu HC, Mo LP, Zhang ZH (2014) RSC Adv 4:12929CrossRefGoogle Scholar
  23. 23.
    Moghaddam FM, Foroushani BK, Rezvani HR (2015) RSC Adv 5:18092CrossRefGoogle Scholar
  24. 24.
    Saeidian H, Abdoli M, Salimi R (2013) C R Chim 16:1063CrossRefGoogle Scholar
  25. 25.
    Estevez V, Villacampa M, Menendez JC (2014) Chem Soc Rev 43:4633CrossRefGoogle Scholar
  26. 26.
    Leeper FJ, Kelly JM (2013) Org Prep Proced Int 45:172CrossRefGoogle Scholar
  27. 27.
    Dong H, Shen M, Redford JE, Stokes BJ, Pumphrey AL, Driver TG (2007) Org Lett 9:5191CrossRefGoogle Scholar
  28. 28.
    Gajengi AL, Sasaki T, Bhanage BM (2015) Catal Commun 72:174CrossRefGoogle Scholar
  29. 29.
    Atar AB, Jeong YT (2013) Tetrahedron Lett 54:5624CrossRefGoogle Scholar
  30. 30.
    Li BL, Li PH, Fang XN, Li CX, Sun JL, Mo LP, Zhang ZH (2013) Tetrahedron 69:7011CrossRefGoogle Scholar
  31. 31.
    Gupta N, Singh KN, Singh J (2014) J Mol Liq 199:470CrossRefGoogle Scholar
  32. 32.
    Hu HC, Liu YH, Li BL, Cui ZS, Zhang ZH (2015) RSC Adv 5:7720CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2016

Authors and Affiliations

  1. 1.Department of ChemistryInstitute of Chemical TechnologyMumbaiIndia

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