Skip to main content
Log in

Cerium ammonium nitrate (CAN)-catalyzed four-component one-pot synthesis of multi-substituted pyrano[2,3-\(\varvec{c}\)]pyrazoles under ultrasound irradiation

  • Full-Length Paper
  • Published:
Molecular Diversity Aims and scope Submit manuscript

Abstract

A convenient and efficient synthesis of multi-substituted dihydropyrano[2,3-c]pyrazole derivatives is reported. The four-component reaction of 4-hydrazinobenzoic acid, \(\beta \)-keto esters, aromatic aldehydes, and malononitrile using 10 mol% CAN catalyst in water under ultrasound irradiation produced the target compounds in good-to-excellent yields. This method has advantages over conventional methods in being economic, non-toxic, and environmentally compatible due to its use of efficient and eco-friendly CAN catalyst and water solvent.

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
Scheme 2

Similar content being viewed by others

References

  1. Zhu J (2003) Recent developments in the isonitrile-based multicomponent synthesis of heterocycles. Eur J Org Chem 7: 1133–1144. doi:10.1002/ejoc.200390167

  2. Dömling A (2006) Recent developments in isocyanide-based multicomponent reactions in applied chemistry. Chem Rev 106:17–89. doi:10.1021/cr0505728

    Article  PubMed  Google Scholar 

  3. Mihovilovic MD, Tanetty P (2007) Metal-assisted multicomponent reactions involving carbon monoxide-towards heterocycle synthesis. Angew Chem Int Ed 46:3612–3615. doi:10.1002/anie.200604743

    Google Scholar 

  4. Weber L (2002) The application of multi-component reactions in drug discovery. Curr Med Chem 9:2085–2093. doi:10.2174/0929867023368719

    Article  PubMed  CAS  Google Scholar 

  5. Paravidino M, Bon RS, Scheffelaar R, Vugts DJ, Znabet A, Schmitz RF, de Kanter FJJ, Stevens CV, Swart M, Bickelhaupt FM, Groen MB, Orru RVA (2006) Diastereoselective multicomponent synthesis of dihydropyridones with an isocyanide functionality. Org lett 8:5369–5372. doi:10.1021/ol062204b

    Article  PubMed  CAS  Google Scholar 

  6. Wang GW, Miao CB (2006) Environmentally benign one-pot multi-component approaches to the synthesis of novel unsymmetrical 4-arylacridinediones. Green Chem 8:1080–1085. doi:10.1039/B604064K

    Article  CAS  Google Scholar 

  7. Pirali T, Tron GC, Zhu J (2006) One-pot synthesis of macrocycles by a tandem three-component reaction and intramolecular [3+2] cycloaddition. Org Lett 8:4145–4148. doi:10.1021/ol061782p

    Article  PubMed  CAS  Google Scholar 

  8. Paravidino M, Scheffelaar R, Schmitz RF, de Kanter FJJ, Groen MB, Ruijter E, Orru RVA (2009) A flexible six-component reaction to access constrained depsipeptides based on a dihydropyridine-one core. J Org Chem 72:10239–10242. doi:10.1021/jo701978v

    Article  Google Scholar 

  9. Magedov IV, Manpadi M, Evdokimov NM, Elias EM, Rozhkova E, Ogasawara MA, Bettale JD, Przhevalskii NM, Rogelj S, Kornienko A (2007) Antiproliferative and apoptosis inducing properties of pyrano[3,2-c]pyridones accessible by a one-step multicomponent synthesis. Bioorg Med Chem Lett 17:3872–3876. doi:10.1016/j.bmcl.2007.05.004

    Article  PubMed  CAS  Google Scholar 

  10. Mecadon H, Rohman MR, Kharbangar I, Laloo BM, Khar-kongor I, Rajbangshi M, Myrboh B (2011) l-Proline as an efficicent catalyst for the multi-component synthesis of 6-amino-4-alkyl/aryl-3-methyl-2,4-dihydropyrano [2,3-c]pyrazole-5-carbonitriles in water. Tetrahedron Lett 52:3228–3231. doi:10.1016/j.tetlet.2011.04.048

    Article  CAS  Google Scholar 

  11. Enders D, Grossmann A, Gieraths B, Düzdemir M, Merkens C (2012) Organocatalytic one-pot asymmetric synthesis of 4H,5H-pyrano[2,3-c]pyrazoles. Org Lett 14:4254–4257. doi:10.1021/ol301983f

    Article  PubMed  CAS  Google Scholar 

  12. Shaabani A, Sarvary A, Rezayan AH, Keshipour S (2009) Synthesis of fully substituted pyrano[2,3-c]pyrazole derivatives via a multicomponent reaction of isocyanides. Tetrahedron 65:3492–3495. doi:10.1016/j.tet.2009.02.035

    Article  CAS  Google Scholar 

  13. Wang JL, Liu D, Zhang ZJ, Shan S, Han X, Srinivasula SM, Croce CM, Alnemri ES, Huang Z (2009) Structure-based discovery of an organic compound that binds Bcl-2 protein and induces apoptosis of tumor cells. Proc Natl Acad Sci USA 97:7124–7129. doi:10.1073/pnas.97.13.7124

    Article  Google Scholar 

  14. Kuo SC, Huang LJ, Nakamura HJ (1984) Studies on heterocyclic compounds. 6. Synthesis and analgesic and antiinflammatory activities of 3,4-dimethylpyrano[2,3-c]pyrazol-6-one derivatives. J Med Chem 27:539–544. doi:10.1021/jm00370a020

    Article  PubMed  CAS  Google Scholar 

  15. van Herk T, Brussee J, Van den Nieuwendijk AMCH, Van Der Klein PAM, IJzerman AP, Stannek C, Lorenzen A (2003) Pyrazole derivatives as partial agonists for the nicotinic acid receptor. J Med Chem 46:3945–3951. doi:35400011275907.0190

    Article  PubMed  Google Scholar 

  16. Zhou JF, Tu SJ, Zhu HQ, Zhi SJ (2002) A facile one pot synthesis of pyrano[2,3-c]pyrazole derivatives under microwave irradiation. Synth Commun 32:3363–3366. doi:10.1081/SCC-120014044

    Article  CAS  Google Scholar 

  17. Ren ZJ, Cao W, Tong W, Jin Z (2005) Solvent-free, one-pot synthesis of pyrano [2,3-c] pyrazole derivatives in the presence of \({\rm KF}{\cdot }2{\rm H}_{2}{\rm O}\) by grinding. Synth Commun 35:2509–2513. doi:10.1080/00397910500212809

    Google Scholar 

  18. Guo SB, Wang SX, Li JT (2007) d,l-Proline-catalyzed one-pot synthesis of pyrans and pyrano[2,3-c]pyrazole derivatives by a grinding method under solvent-free conditions. Synth Commun 37:2111–2120. doi:10.1080/00397910701396906

    Article  CAS  Google Scholar 

  19. Ablajan K, Maimaiti Z (2012) An efficient four-component synthesis of multisubstituted pyrano[2,3-c]pyrazole. Synth Commun 42:1959–1966. doi:10.1080/00397911.2010.551169

    Article  CAS  Google Scholar 

  20. Mecadon H, Rohman MR, Rajbangshi M, Myrboh B (2011) \(\gamma \)-Alumina as a recyclable catalyst for the four-component synthesis of 6-amino-4-alkyl/aryl-3-methyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitriles in aqueous medium. Tetrahedron Lett 52:2523–2525. doi:10.1016/j.tetlet.2011.03.036

    Google Scholar 

  21. Chavan HV, Babar SB, Hoval RU, Bandgar BP (2011) Rapid one-pot, four component synthesis of pyranopyrazoles using heteropolyacid under solvent-free condition. Bull Korean Chem Soc 32:3963. doi:10.5012/bkcs.2011.32.11.3963

    Article  CAS  Google Scholar 

  22. Mason TJ (1992) Industrial sonochemistry: potential and practicality. Ultrasonics 30:192–196. doi:10.1016/0041-624X(92)90072-T

    Article  CAS  Google Scholar 

  23. Asakura Y, Nishida T, Matsuoka T, Koda S (2008) Effects of ultrasonic frequency and liquid height on sonochemical efficiency of large-scale sonochemical reactors. Ultrason Sonochem 15: 244–250. doi:10.1016/j.ultsonch.2007.03.012

    Google Scholar 

  24. Fiametti KG, Sychoski MM, Cesaro AD, Furigo A, Bretanhac LC, Pereira CMP, Treichel H, Oliveira D, Oliveira JV (2011) Ultrasound irradiation promoted efficient solvent-free lipase-catalyzed production of mono- and diacylglycerols from olive oil. Ultrason Sonochem 18:981–987. doi:10.1016/j.ultsonch.2010.11.010

    Article  PubMed  CAS  Google Scholar 

  25. Li JT, Han JF, Yang JH, Li TS (2003) An efficient synthesis of 3,4-dihydropyrimidin-2-ones catalyzed by \({\rm NH}_{2}{\rm SO}_{3}{\rm H}\) under ultrasound irradiation. Ultrason Sonochem 10:119–122. doi: 10.1016/S1350-4177(03)00092-0

    Article  PubMed  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by the Natural Science Foundation of China (No. 21162028) and the Natural Science Foundation of the Xinjiang Science Technology Agency (No. 2009 211A02).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Keyume Ablajan.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (pdf 2037 KB)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ablajan, K., Liju, W., Kelimu, Y. et al. Cerium ammonium nitrate (CAN)-catalyzed four-component one-pot synthesis of multi-substituted pyrano[2,3-\(\varvec{c}\)]pyrazoles under ultrasound irradiation. Mol Divers 17, 693–700 (2013). https://doi.org/10.1007/s11030-013-9465-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11030-013-9465-7

Keywords

Navigation