Journal of Chemical Sciences

, 131:105 | Cite as

Development of novel pyrazolones by using SiO2/ZnCl2 – green approach

  • G Neelima
  • K Lakshmi
  • K Sesha MaheswarammaEmail author
Regular Article


The present research work deals with the green synthesis of substituted pyrazolone derivatives 4(a–f) from 2,4-dinitrophenylhydrazine with various substituted aromatic aldehyde and ethyl acetoacetate in the presence of silica-supported zinc chloride (SiO2/ZnCl2) as a recyclable Lewis acid catalyst. The synthesized compounds were structurally characterized with IR, 1H NMR, Mass spectra and elemental analysis. All these compounds were tested for their antioxidant activity by using the DPPH radical scavenging method.

Graphic abstract

Synthetic Scheme of pyrazolone derivatives


Pyrazolone silica-supported zinc chloride catalyst green synthesis anti-oxidant activity 



The authors thank the Management and the Principal of Sri Venkateswara College of Pharmacy, Chittoor for providing the facilities and financial assistance to carry out this study. They are also thankful to SIF, VIT University, Vellore for the spectral analysis.

Supplementary material

12039_2019_1679_MOESM1_ESM.pdf (797 kb)
Supplementary material 1 (PDF 798 kb)


  1. 1.
    Chanshetti U 2014 Green chemistry: Environmentally benign chemistry Chem. Sci. 1 110Google Scholar
  2. 2.
    Bhattacharjee D, Sheet S K, Khatua S, Biswas K, Joshi S and Myrboh B 2018 A reusable magnetic nickel nanoparticle based catalyst for the aqueous synthesis of diverse heterocycles and their evaluation as potential antibacterial agent Bio. Med. Chem. 26 5018CrossRefGoogle Scholar
  3. 3.
    El-Hawash S A M, Badawey E A M and El-Ashmawey I M 2006 Nonsteroidal antiinflammatory agents part 2 antiinflammatory, analgesic and antipyretic activity of some substituted 3-pyrazolin-5-ones and 1,2,4,5,6,7-3H-hexahydroindazol-3-ones Eur. J. Med. Chem. 41 155CrossRefGoogle Scholar
  4. 4.
    Gaffer H E, Abdel-Fattah S, Etman H A and Abdel-Latif E 2017 Synthesis and antioxidant activity of some new thiazolyl–pyrazolone derivatives J. Heterocycl. Chem. 54 331CrossRefGoogle Scholar
  5. 5.
    Seham Y and Hassan 2013 Synthesis, antibacterial and antifungal activity of some new pyrazoline and pyrazole derivatives Molecules 18 2683CrossRefGoogle Scholar
  6. 6.
    El-Gaby M S A, Ghorab M M, Ismail Z H, Abdel-Gawad S M and Aly H M 2017 Synthesis, structural characterization and anticancer evaluation of pyrazole derivatives Med. Chem. Res. 27 72Google Scholar
  7. 7.
    Al-Mutairi A A, El-Baih F E M and Al-Hazim H M 2010 Microwave versus ultrasound assisted synthesis of some new heterocycles based on pyrazolone moiety J. Saudi Chem. Soc. 14 287CrossRefGoogle Scholar
  8. 8.
    Pal S, Mareddy J and Devi N S 2008 High speed synthesis of pyrazolones using microwave-assisted neat reaction technology J. Braz. Chem. Soc. 19 1207CrossRefGoogle Scholar
  9. 9.
    Mousa S A S, Ishak E A, Bakheet M E M and Shanab F A 2015 A new route for the synthesis of pyrazolone derivatives Elixir Org. Chem. 89 36854Google Scholar
  10. 10.
    Gupta P and Gupta J K 2016 Synthesis and In-vitro antifungal evaluation of 5-pyrazolones Open Chem. J. 3 17CrossRefGoogle Scholar
  11. 11.
    Gunkara O T, Bagdatli E and Ocal N 2013 Synthesis of new pyrazolone dyes J. Chem. Res. 37 227CrossRefGoogle Scholar
  12. 12.
    Zang H, Su Q, Guo S, Mo Y and Cheng B 2011 An efficient one‐pot synthesis of pyrazolone derivatives promoted by acidic ionic liquid Chin. J. Chem. 29 2202Google Scholar
  13. 13.
    Ziarati A, Ghomi J S and Rohani S 2013 Sonochemically synthesis of pyrazolones using reusable catalyst CuI nanoparticles that was prepared by sonication Ultrason. Sonochem. 20 1069CrossRefGoogle Scholar
  14. 14.
    Min Z L and Hu X M 2013 Tungstophosphoric Acid-Catalyzed Synthesis of Pyrazolones in Water Asian J. Chem. 25 7290Google Scholar
  15. 15.
    Sobhani S, Hasaninejad A, Maleki M F and Parizi Z P 2012 Tandem Knoevenagel–Michael reaction of 1-phenyl-3-methyl-5-pyrazolone with aldehydes using 3-aminopropylated silica gel as an efficient and reusable heterogeneous catalyst Synth. Commun. 42 2245Google Scholar
  16. 16.
    Niknam K and Mirzaee S 2011 Silica sulfuric acid, an efficient and recyclable solid acid catalyst for the synthesis of 4,4′-(arylmethylene)bis (1H-pyrazol-5-ols) Synth. Commun. 41 2403Google Scholar
  17. 17.
    Baghernejad M and Niknam K 2012 Synthesis of 4,4′-(arylmethylene)bis(1h-pyrazol-5-ols) using silica-bonded ionic liquid as recyclable catalyst Int. J. Chem. 4 52CrossRefGoogle Scholar
  18. 18.
    Wang W, Wang S X, Qin X Y and Li J T 2005 Reaction of aldehydes and pyrazolones in the presence of sodium dodecyl sulfate in aqueous media Synth. Commun. 35 1263Google Scholar
  19. 19.
    Kuarm B S and Rajitha B 2012 Xanthan sulfuric acid: An efficient, biosupported, and recyclable solid acid catalyst for the synthesis of 4,4′-(arylmethylene)bis(1H-pyrazol-5-ols) Synth. Commun. 42 2382Google Scholar
  20. 20.
    Khazaei A, Zolfigol M A, Moosavi Zare A R, Asgari Z, Shekouhy M, Zare A and Hasaninejad A 2012 Preparation of 4,4’-(arylmethylene)-bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)s over 1,3-disulfonic acid imidazolium tetrachloroaluminate as a novel catalyst RSC Adv. 2 8010Google Scholar
  21. 21.
    Tayebi S and Niknam K 2012 Synthesis of 4,4′-(arylmethylene)bis(1H-pyrazol-5-ols) via multi-component reactions by using silica-bonded sulfamic acid derivatives Iran. J. Catal. 2 69Google Scholar
  22. 22.
    Martins D M, Torres B G, Spohr P R, Machado P, Bonacorso H G and Zanatta N 2008 Antioxidant potential of new pyrazoline derivatives to prevent oxidative damage Basic Clin. Pharmacol. Toxicol. 104 107Google Scholar
  23. 23.
    Tamaddon F and Tavakoli F 2011 One-pot synthesis of N-tert-butyl amides from alcohols, ethers and esters using ZnCl2/SiO2 as a recyclable heterogeneous catalyst J. Mol. Catal. A: Chem. 337 52CrossRefGoogle Scholar
  24. 24.
    Prajapati S P, Patel D P and Patel P S 2012 Synthesis and characterization of 6-amino-4-(substituted phenyl)-1-(2,4-dinitrophenyl)-3-methyl-pyrazolo[3,4-b]pyridine-5-carbonitrile Elixir Org. Chem. 48 9414Google Scholar
  25. 25.
    Gupta A K, Kalpana S and Malik J K 2012 Synthesis and in vitro antioxidant activity of new 3-substituted-2-oxindole derivatives Indian J. Pharma. Sci. 74 481Google Scholar
  26. 26.
    Sreejayan N and Rao MNA 1996 Free radical scavenging activity by curcuminoids Drug Res. 46 169Google Scholar
  27. 27.
    Mahesh B, Mohan G, Santhisudha S, Sridevi C, Vasudeva R N, Vijaya T and Suresh R C 2017 Synthesis and antioxidant activity of some new N-alkylated pyrazole-containing benzimidazole Chem. Heterocycl. Comp. 53 173CrossRefGoogle Scholar
  28. 28.
    Anka P, Aleksandra M, Jovana J, Marko P, Danijela I K, Ivan D, Dragana S, Vladimir M and Jelena K 2018 Synthesis, characterization, antioxidant and antimicrobial activity of novel 5- arylidene-2-ferrocenyl-1,3-thiazolidin-4-ones J. Organometal. Chem. 869 1CrossRefGoogle Scholar
  29. 29.
    Wang S, Zhang Z, Liua B and Li J 2013 Silica coated magnetic Fe3O4 nanoparticles supported phosphotungstic acid: a novel environmentally friendly catalyst for the synthesis of 5-ethoxymethylfurfural from 5-hydroxymethylfurfural and fructose Catal. Sci. Technol. 3 2104Google Scholar

Copyright information

© Indian Academy of Sciences 2019

Authors and Affiliations

  1. 1.JNTU, AnanthapuramuAnantapurIndia
  2. 2.Department of Pharmaceutical AnalysisSri Venkateswara College of PharmacyChittoorIndia
  3. 3.Department of ChemistryJNTU College of Engineering (Autonomous) PulivendulaPulivendulaIndia

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