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One-pot multicomponent click synthesis of pyrazole derivatives using cyclodextrin-supported capsaicin nanoparticles as catalyst

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Abstract

Facile and efficient methodology for one-pot multicomponent click synthesis of pyrazole derivatives by using phenyl hydrazine, malononitrile and varying degrees of substituted aldehydes has been described. As a recyclable heterogeneous catalyst, we used CPS-CDMNPs. The nanoparticles were prepared by two-step synthesis using co-precipitation and ultrasonication method for the synthesis of CDMNPs, and further capsaicin was deposited on CDMNPs by wet impregnation method. The catalyst can be recovered in a facile manner from the reaction mixture magnetically by applying magnet outside the flask. Moreover, this protocol features the shortest reaction time, simple procedure, high conversion and no tedious workup procedures.

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References

  1. Dar AM, Shamsuzzaman (2015) Review on the synthesis of pyrazole heterocycles. Nucl Med Radiat Ther 6:250–254

    Google Scholar 

  2. Bekhit AA, Hymete A, Asfaw H, Bekhit AEA (2012) Synthesis and biological evaluation of some pyrazole derivatives as anti-malarial agents. Arch Pharm 345(2):147–154

    Article  Google Scholar 

  3. Jamwal A, Javed A, Bhardwaj V (2013) A review on Pyrazole derivatives of pharmacological potential. J Pharm BioSci 3:114–123

    Google Scholar 

  4. Du K, Mei Y, Cao X et al (2013) The synthesis of pyrazole derivatives based on glucose. Int J Chem Eng Appl 4:2011–2013

    Google Scholar 

  5. Mert S, Kasimogullari R, Ok S (2014) A short review on pyrazole derivatives and their applications. J Postdoc Res 2:64–72

    Google Scholar 

  6. Kumar KA, Jayaroopa P (2013) Pyrazoles: synthetic strategies and their pharmaceutical applications-an overview. Int J PharmTech Res 5:1473–1486

    Google Scholar 

  7. Palermo V, Sathicq A, Liberto N et al (2016) Calix[n]arenes: active organocatalysts for the synthesis of densely functionalized piperidines by one-pot multicomponent procedure. Tetrahedron Lett 57:2049–2054

    Article  Google Scholar 

  8. Welsch SJ, Umkehrer M, Ross G et al (2011) Pd II/IV catalyzed oxidative cyclization of 1, 6-enynes derived by Ugi-4-component reaction. Tetrahedron Lett 52:6295–6297

    Article  Google Scholar 

  9. Dondoni A (2007) Triazole: the keystone in glycosylated molecular architectures constructed by a click reaction. Chem Asian J 2:700–708

    Article  Google Scholar 

  10. Golas PL, Matyjaszewski K (2010) Marrying click chemistry with polymerization: expanding the scope of polymeric materials. Chem Soc Rev 39:1338–1354

    Article  Google Scholar 

  11. Gawande MB, Goswami A, Asefa T et al (2015) Core-shell nanoparticles: synthesis and applications in catalysis and electrocatalysis. Chem Soc Rev 44:7540–7590

    Article  Google Scholar 

  12. Ito A, Shinkai M, Honda H, Kobayashi T (2005) Medical application of functionalized magnetic nanoparticles. J Biosci Bioeng 100:1–11

    Article  Google Scholar 

  13. Wang D, Astruc D (2014) Fast-growing field of magnetically recyclable nanocatalysts. Chem Rev 114:6949–6985

    Article  Google Scholar 

  14. Gref R, Quellec P, Sanchez A et al (2001) Development and characterization of CyA-loaded poly (lactic acid)-poly (ethylene glycol) PEG micro- and nanoparticles. Comparison with conventional PLA particulate carriers. Eur J Pharm Biopharm 51:111–118

    Article  Google Scholar 

  15. Dresco PA, Zaitsev VS, Gambino RJ, Chu B (1999) Preparation and properties of magnetite and polymer magnetite nanoparticles. Langmuir 15:1945–1951

    Article  Google Scholar 

  16. Sinniah S, Mohamad S, Manan NSA (2015) Magnetite nanoparticles coated with β-cyclodextrin functionalized-ionic liquid: synthesis and its preliminary investigation as a new sensing material. Appl Surf Sci 357:543–550

    Article  Google Scholar 

  17. Pralhad T, Rajendrakumar K (2004) Study of freeze-dried quercetin-cyclodextrin binary systems by DSC, FT-IR, X-ray diffraction and SEM analysis. J Pharm Biomed Anal 34:333–339

    Article  Google Scholar 

  18. Yallapu MM, Jaggi M, Chauhan SC (2010) β-Cyclodextrin-curcumin self-assembly enhances curcumin delivery in prostate cancer cells. Colloids Surf B Biointerfaces 79:113–125

    Article  Google Scholar 

  19. Goycoolea FM, Valle-Gallego A, Stefani R et al (2012) Chitosan-based nanocapsules: physical characterization, stability in biological media and capsaicin encapsulation. Colloid Polym Sci 290:1423–1434

    Article  Google Scholar 

  20. Zhang Y, Huang Z, Omari-Siaw E et al (2016) Preparation and in vitro–in vivo evaluation of sustained-release matrix pellets of capsaicin to enhance the oral bioavailability. AAPS PharmSciTech 17:339–349

    Article  Google Scholar 

  21. Arora P, Rajput JK, Singh H (2015) Nanostructured oxytyramine catalyst for the facile one-pot synthesis of cyclohexanecarbonitrile derivatives. RSC Adv 5:97212–97223

    Article  Google Scholar 

  22. Singh H, Rajput JK, Arora P, Jigyasa J (2016) Role of (3-aminopropyl)tri alkoxysilanes in grafting of chlorosulphonic acid immobilized magnetic nanoparticles and their application as heterogeneous catalysts for the green synthesis of α-aminonitriles. RSC Adv 6:84658–84671

    Article  Google Scholar 

  23. Reyes-Escogido M, Gonzalez-Mondragon EG, Vazquez-Tzompantzi E (2011) Chemical and pharmacological aspects of capsaicin. Molecules 16:1253–1270

    Article  Google Scholar 

  24. Liu Y, Liu P, Su Z et al (2008) Attapulgite–Fe3O4 magnetic nanoparticles via co-precipitation technique. Appl Surf Sci 255:2020–2025

    Article  Google Scholar 

  25. Chen L, Berry RM, Tam KC (2014) Synthesis of β-Cyclodextrin-modified cellulose nanocrystals (CNCs)@Fe3O4@SiO2 superparamagnetic nanorods. ACS Sustain Chem Eng 2:951–958

    Article  Google Scholar 

  26. Domínguez-Martínez I, Meza-Márquez OG, Osorio-Revilla G et al (2014) Determination of capsaicin, ascorbic acid, total phenolic compounds and antioxidant activity of Capsicum annuum L. var. serrano by mid infrared spectroscopy (Mid-FTIR) and chemometric analysis. J Korean Soc Appl Biol Chem 57:133–142

    Article  Google Scholar 

  27. Zhu J, Wang P, Lu M (2013) β-Cyclodextrin coated Fe3O4 nanoparticles: a simple preparation and application for selective oxidation of alcohols in water. J Braz Chem Soc 24:171–176

    Article  Google Scholar 

  28. Khalfaoui M, Knani S, Hachicha MA, Lamine AB (2003) New theoretical expressions for the five adsorption type isotherms classified by BET based on statistical physics treatment. J Colloid Interface Sci 263:350–356

    Article  Google Scholar 

  29. Gałuszka A, Migaszewski Z, Namieśnik J (2013) The 12 principles of green analytical chemistry and the SIGNIFICANCE mnemonic of green analytical practices. TrAC Trends Anal Chem 50:78–84

    Article  Google Scholar 

  30. Srivastava M, Rai P, Singh J, Singh J (2013) An environmentally friendlier approach—ionic liquid catalysed, water promoted and grinding induced synthesis of highly functionalised pyrazole derivatives. RSC Adv 3:16994

    Article  Google Scholar 

  31. Srivastava M, Rai P, Singh J, Singh J (2014) Efficient iodine-catalyzed one pot synthesis of highly functionalised pyrazoles in water. New J Chem 38:302–307

    Article  Google Scholar 

  32. Nemati F, Nikkhah SH, Elhampour A (2015) An environmental friendly approach for the catalyst-free synthesis of highly substituted pyrazoles promoted by ultrasonic radiation. Chinese Chem Lett 26:1397–1399

    Article  Google Scholar 

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Acknowledgements

We are thankful to SAIF, Panjab University, Chandigarh, for FT‐IR, TEM and 1H‐NMR, IIT Ropar for SEM, XRD, 1H‐NMR, 13C‐NMR, CSMCRI Bhavnagar and BIT Bengaluru for BET, CIL IIT Roorkee for VSM. DST-FIST New Delhi, for financial assistance for acquiring the FT-IR at NIT Jalandhar. One of the author (P.A.) is thankful to MHRD and NIT Jalandhar for providing the research fellowship. We would like to thank Mr. Harminder Singh and Miss Jigyasa Badhan for their valuable suggestions in manuscript writing.

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Correspondence to Priya Arora.

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Arora, P., Rajput, J.K. One-pot multicomponent click synthesis of pyrazole derivatives using cyclodextrin-supported capsaicin nanoparticles as catalyst. J Mater Sci 52, 11413–11427 (2017). https://doi.org/10.1007/s10853-017-1304-2

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  • DOI: https://doi.org/10.1007/s10853-017-1304-2

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