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SCMNPs@Uridine/Zn: An efficient and reusable heterogeneous nanocatalyst for the rapid one-pot synthesis of tricyclic fused pyrazolopyranopyrimidine and 3-methyl carboxylate substituted pyrano[2,3-c]pyrazole derivatives under solvent-free conditions

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Języki publikacji
EN
Abstrakty
EN
SCMNPs@Uridine/Zn is utilized as an environmental-friendly and efficient heterogeneous nanocatalyst for two one-pot four-component condensation reactions, containing hydrazine hydrate, arylaldehyde, ethyl acetoacetate, and barbituric acid to yield tricyclic fused pyrazolopyranopyrimidine derivatives (5a-q), and hydrazine hydrate, arylaldehyde, malononitrile, and dimethyl acetylenedicarboxylate/diethyl acetylenedicarboxylate to yield 3-methyl carboxylate substituted pyrano[2,3-c]pyrazole derivatives (8a-y) under solvent-free conditions with high to excellent yields. The main advantages of this process are easy work-up, short reaction times, no chromatographic purifications, and recyclability of the catalyst for a minimum of six runs without any signifcant decrease in yields of the products. Also, the prepared catalyst SCMNPs@Uridine/Zn was synthesized and fully characterized by various techniques including Fourier transform infrared spectroscopy (FT-IR), energy dispersive X-ray (EDX), thermogravimetric analysis (TGA), X-ray diffraction (XRD), vibrating sample magnetometer (VSM) and Raman spectroscopy.
Rocznik
Strony
20--33
Opis fizyczny
Bibliogr. 47 poz., rys., tab.
Twórcy
autor
  • Gansu Agricultural University, Institute of Agricultural Resources Chemistry and Application, College of Science, Gansu Province, 730000, China
autor
  • Gansu Agricultural University, Institute of Agricultural Resources Chemistry and Application, College of Science, Gansu Province, 730000, China
autor
  • Gansu Agricultural University, Institute of Agricultural Resources Chemistry and Application, College of Science, Gansu Province, 730000, China
  • Gansu Agricultural University, Institute of Agricultural Resources Chemistry and Application, College of Science, Gansu Province, 730000, China
  • University of Al-Qadisiyah, College of Science, Department of Chemistry, Republic of Iraq
Bibliografia
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  • 3. Mori, K., Hara, T., Mizugaki, T., Ebitani, K. & Kaneda, K. (2004). Hydroxyapatite-supported palladium nanoclusters: a highly active heterogeneous catalyst for selective oxidation of alcohols by use of molecular oxygen. J. Amer. Chem. Soc. 126(34), 10657–10666. DOI:10.1021/ja0488683.
  • 4. Mahmoudi, M., Sant, S., Wang, B., Laurent, S. & Sen, T. (2011). Superparamagnetic iron oxide nanoparticles (SPIONs): development, surface modification and applications in chemotherapy. Adv. Drug Delivery Rev. 63(1–2), 24–46. DOI:10.1016/j.addr.2010.05.006.
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  • 8. Kotarba, A., Bieniasz, W., Kuśtrowski, P., Stadnicka, K. & Sojka, Z. (2011). Composite ferrite catalyst for ethylbenzene dehydrogenation: Enhancement of potassium stability and catalytic performance by phase selective doping. Appl. Catal. A: General, 407(1–2), 100–105. DOI:10.1016/j.apcata.2011.08.029.
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  • 22. Mecadon, H., Rohman, M.R., Kharbangar, I., Laloo, B.M., Kharkongor, 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 Letters, 52(25), 3228–3231. DOI:10.1016/j.tetlet.2011.04.048.
  • 23. Mecadon, H., Rohman, M.R., Rajbangshi, M. & Myrboh, B. (2011). γ-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 Letters, 52(19), 2523–2525. DOI:10.1016/j.tetlet.2011.03.036.
  • 24. Reddy, M.M., Jayashankara, V.P. & Pasha, M.A. (2010). Glycine-catalyzed efficient synthesis of pyranopyrazoles via one-pot multicomponent reaction. Synthetic Communications®, 40(19), 2930–2934. DOI:10.1080/00397910903340686.
  • 25. Siddekha, A., Nizam, A. & Pasha, M.A. (2011). An efficient and simple approach for the synthesis of pyranopyrazoles using imidazole (catalytic) in aqueous medium, and the vibrational spectroscopic studies on 6-amino-4-(4′-methoxyphenyl)-5-cyano-3-methyl-1-phenyl-1, 4-dihydropyrano [2, 3-c] pyrazole using density functional theory. Spectrochim. Acta Part A: Molec. Biomol. Spectrosc. 81(1), 431–440. DOI:10.1016/j.saa.2011.06.033.
  • 26. Mohamed, N.R., Khaireldin, N.Y., Fahmyb, A.F. & El-Sayeda, A.A.F. (2010). Facile synthesis of fused nitrogen containing heterocycles as anticancer agents. Der. Pharm. Chem. 2, 400–417.
  • 27. Prasad, Y.R., Rao, A.L., Prasoona, L., Murali, K. & Kumar, P.R. (2005). Synthesis and antidepressant activity of some 1, 3, 5-triphenyl-2-pyrazolines and 3-(2 ″-hydroxy naphthalen-1 ″-yl)-1, 5-diphenyl-2-pyrazolines. Bioorg. & Med. Chem. Letters, 15(22), 5030–5034. DOI:10.1016/j.bmcl.2005.08.040.
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  • 31. Bagley, M.C., Hughes, D.D., Lubinu, M.C., Merritt, E.A., Taylor, P.H. & Tomkinson, N.C. (2004). Microwave-assisted synthesis of pyrimidine libraries. QSAR & Combinat. Sci. 23(10), 859–867. DOI:10.1002/qsar.200420044.
  • 32. Kamdar, N.R., Haveliwala, D.D., Mistry, P.T., & Patel, S.K. (2010). Design, synthesis and in vitro evaluation of antitubercular and antimicrobial activity of some novel pyranopyrimidines. Europ. J. Med. Chem. 45(11), 5056–5063. DOI:10.1016/j.ejmech.2010.08.014.
  • 33. Heravi, M.M., Mousavizadeh, F., Ghobadi, N., & Tajbakhsh, M. (2014). A green and convenient protocol for the synthesis of novel pyrazolopyranopyrimidines via a one-pot, four-component reaction in water. Tetrahedron Letters, 55(6), 1226–1228. DOI:10.1016/j.tetlet.2014.01.004.
  • 34. Khodabakhshi, S., Rashidi, A., Tavakoli, Z., Baghernejad, M., & Yadegari, A. (2016). The first catalytic application of oxidized carbon nanotubes in a four-component synthesis of fused heterocycles. Monatshefte für Chemie-Chemical Monthly, 147(4), 791–795. DOI:10.1007/s00706-015-1532-6.
  • 35. Dastkhoon, S., Tavakoli, Z., Khodabakhshi, S., Baghernejad, M. & Abbasabadi, M.K. (2015). Nanocatalytic onepot, four-component synthesis of some new triheterocyclic compounds consisting of pyrazole, pyran, and pyrimidinone rings. J. Chem. 39(9), 7268–7271. DOI:10.1039/C5NJ01046B.
  • 36. Wang, S., Izquierdo, J., Rodríguez-Escrich, C. & Pericà s, M.A. (2017). Asymmetric [4+ 2] Annulation Reactions Catalyzed by a Robust, Immobilized Isothiourea. ACS Catal. 7(4), 2780–2785. DOI:10.1021/acscatal.7b00360.
  • 37. Ganesan, A., Kothandapani, J. & Subramaniapillai, S.G. (2016). Extending the scope of oleic acid catalysis in diversityoriented synthesis of chromene and pyrimidine based scaffolds. RSC Adv. 6(25), 20582–20587. DOI:10.1039/C6RA02507B.
  • 38. Li, X.T., Zhao, A.D., Mo, L.P. & Zhang, Z.H. (2014). Meglumine catalyzed expeditious four-component domino protocol for synthesis of pyrazolopyranopyrimidines in aqueous medium. RSC Adv. 4(93), 51580–51588. DOI:10.1039/C4RA08689A.
  • 39. Safaei-Ghomia, J., Asgari-Kheirabadia, M., ShahbaziAlavia, H. & Ziaratib, A. (2016). Synthesis of methyl 6-amino-5-cyano-4-aryl-2, 4-dihydropyrano [2, 3-c] pyrazole-3-carboxylates using nano-ZnZr4 (PO4) 6 as an efficient catalyst. Iranian J. Catal. 6(4), 319–324.
  • 40. Safaei-Ghomi, J., Asgari-Kheirabadi, M., & ShahbaziAlavi, H. (2016). Environmentally benign synthesis of methyl 6-amino-5-cyano-4-aryl-2, 4-dihydropyrano [2, 3-c] pyrazole3-carboxylates using CeO2 nanoparticles as a reusable and robust catalyst. Zeitschrift für Naturforschung B, 71(11), 1135–1140. DOI:10.1515/znb-2016-0119.
  • 41. Zonouz, A.M., Eskandari, I., & Khavasi, H.R. (2012). A green and convenient approach for the synthesis of methyl 6-amino-5-cyano-4-aryl-2, 4-dihydropyrano [2, 3-c] pyrazole3-carboxylates via a one-pot, multi-component reaction in water. Tetrahedron Letters, 53(41), 5519–5522. DOI:10.1016/j.tetlet.2012.08.010.
  • 42. Azzam, S.H.S. & Pasha, M.A. (2012). Simple and efficient protocol for the synthesis of novel dihydro-1H-pyrano [2, 3-c] pyrazol-6-ones via a one-pot four-component reaction. Tetrahedron Letters, 53(50), 6834–6837. DOI:10.1016/j.tetlet.2012.10.025.
  • 43. Bihani, M., Bora, P.P., Bez, G., & Askari, H. (2013). Amberlyst A21 catalyzed chromatography-free method for multicomponent synthesis of dihydropyrano [2, 3-c] pyrazoles in ethanol. ACS Sustain. Chem. & Engin. 1(4), 440–447. DOI:10.1021/sc300173z.
  • 44. Ambethkar, S., Padmini, V. & Bhuvanesh, N. (2015). A green and effi cient protocol for the synthesis of dihydropyrano [2, 3-c] pyrazole derivatives via a one-pot, four component reaction by grinding method. J. Adv. Res. 6(6), 975–985. DOI:10.1016/j.jare.2014.11.011.
  • 45. Bhaskaruni, S.V., Maddila, S., van Zyl, W.E., & Jonnalagadda, S.B. (2018). An efficient and green approach for the synthesis of 2, 4-dihydropyrano [2, 3-c] pyrazole-3-carboxylates using Bi 2 O 3/ZrO 2 as a reusable catalyst. RSC Adv. 8(29), 16336–16343. DOI:10.1039/C8RA01994K.
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Uwagi
Opracowanie rekordu ze środków MNiSW, umowa Nr 461252 w ramach programu "Społeczna odpowiedzialność nauki" - moduł: Popularyzacja nauki i promocja sportu (2020).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-c6daf656-0525-438d-b8a3-fb32453b0eb8
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