Brønsted Acidic Phosphonium Based Ionic Liquid Functionalized SBA-15 [HO3S-PhospIL@SBA-15]: Green, Recyclable, and Efficient Catalyst for the Synthesis of Pyrano[3,2-c]Chromenone Derivatives

Document Type : Research Article

Authors

1 Medicinal Plants Research Center, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, I.R. IRAN

2 Department of Chemistry, Tehran-North Branch, Islamic Azad University, Zafar St, Tehran, I.R. IRAN

3 Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, I.R. IRAN

Abstract

The surface of SBA-15 was modified by diphenylphosphine; then, it was treated with butane sultone and sulfuric acid to obtain Brønsted acid HO3S-phosphonium based ionic liquid functionalized SBA-15 with HSO4- as a counteranion. It efficiently catalyzed synthesis of pyrano[3,2-c]chromenone derivatives through the reaction of 4-hydroxycoumarin and chalcones at 60 °C in water/ethanol. Good yields, mild reaction conditions, and user-friendly procedure are advantages of this method. Also, the catalyst could be easily separated and reused five times without significant reduction of activity.  

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References

[1] Boon J.A., Levinsky J.A., Pflug J.L., Wilkes J.S., Friedel-Crafts Reactions in Ambient-Temperature Molten Salts, J. Org. Chem., 51: 480-483 (1986).
[2] a)  Petkovic M., Seddon K.R., Petkovic M., Seddon K.R., Rebelo L.P.N.,  Pereira C.S., Ionic Liquids:
A Pathway to Environmental Acceptability, Chem. Soc. Rev., 40: 1383-1403 (2011).
     b) Li Y.-F., Yuan, Y.-P., Wang K.-K., Jia J., Qin X.-L., Xu Y., Conversion of Sawdust Into
5-Hydroxymethylfurfura by Using 1,3-Dimethyl-2-Imidazolidinone as the Solvent, Iran. J. Chem. Chem. Eng. (IJCCE), 32(3): 75-79 (2013).
[3] Valkenberg M.H., deCastro C., Hölderich W.F., Immobilisation of Ionic Liquids on Solid Supports, Green Chem., 4: 88-93 (2002).
[4] Öchsner E., Schneider M.J., Meyer C., Haumann M., Wasserscheid P., Challenging the Scope of Continuous, Gas-Phase Reactions with Supported Ionic Liquid Phase (SILP) Catalysts-Asymmetric Hydrogenation of Methyl Acetoacetate,  Appl. Catal. A: Gen., 399: 35-41 (2011).
[5] Beck J.S., Vartuli J.C., Roth W.J., Leonowicz M.E., Kresge C.T., Schmitt K.D., Chu C.T-W., Olson D.H., Sheppard E.W., McCullen S.B., Higgins J.B., Schlenkert J.L., A New Family of Mesoporous Molecular Sieves Prepared with Liquid Crystal Templates, J. Am. Chem. Soc., 114: 10834-10843 (1992).
[6] Huirache-Acuña R., Nava R., Peza-Ledesma C.L., Lara-Romero J., Alonso-Núñez G., Pawelec B., Rivera-Muñoz E.M., SBA-15 Mesoporous Silica as Catalytic Support for Hydrodesulfurization Catalysts-Review, Materials, 6: 4139-4167 (2013).
[7] Rahmat N., Zuhairi A.A., Mohamed A.R., A Review: Mesoporous Santa Barbara Amorphous-15, Types, Synthesis and its Applications Towards Biorefinery Production, Am. J. Appl. Sci., 7: 1579-1586 (2010).
[8] McKee T.C., Fuller R.W., Covington  C.D., Cardellina J.H., Gulakowski R.J., Krepps B.L., McMahon J.B., Boyd M.R.,  New Pyranocoumarins Isolated from Calophyllum lanigerum and Calophyllum teysmannii, J. Nat. Prod., 59:
754-758 (1996).
[9] Chun-Hui M., Chen B., Qi H.-Y., Li B.-G., Zhang G.-L., Two Pyranocoumarins from the Seeds of Calophyllum polyanthum, J. Nat. Prod.,67: 1598-1600 (2004).
[10] Xu Z.Q., Pupek K., Suling W.J., Enache L., Flavin M.T., Pyranocoumarin, A Novel Anti-TB Pharmacophore: Synthesis and Biological Evaluation Against Mycobacterium Tuberculosis, Bioorg. Med. Chem., 14: 4610-4626 (2006).
[11] Mao W., Wang T., Zeng H., Wang Z., Chen J., Shen J., Synthesis and Evaluation of Novel Substituted
5-Hydroxycoumarin and Pyranocoumarin Derivatives Exhibiting Significant Antiproliferative Activity Against Breast Cancer Cell Lines, Bioorg. Med. Chem. Lett., 19: 4570-4573 (2009).
[12] Kongkathip B., Kongkathip N., Sunthitikawinsakul A., Napaswat C., Yoosook C., Anti-HIV-1 Constituents from Clausena Excavata: Part II. Carbazoles and A Pyranocoumarin, Phytother. Res., 19: 728-731      (2005).
[13] Symeonidis T., Fylaktakidou K.C., Hadjipavlou-Litina D.J., Litinas K.E., Synthesis and Anti-Inflammatory Evaluation of Novel Angularly or Linearly Fused Coumarins, Eur. J. Med. Chem., 44: 5012-5017 (2009).
[14] Lee H.J., Lee H.J., Lee E.O., Lee J.H., Lee K.S., Kim K.H., Kim S.-H., Lü J., In Vivo Anti-Cancer Activity of Korean Angelica Gigas and Its Major Pyranocoumarin Decursin, Am. J. Chin. Med., 37: 127-142 (2009).
[15] Oketch-Rabah H.A., Lemmich E., Dossaji S.F., Theander T.G., Olsen C.E., Cornett C., Kharazmi A., Christensen S.B., Two New Antiprotozoal 5-Methylcoumarins from Vernonia Brachycalyx, J. Nat. Prod., 60: 458-461 (1997).
[16] Moreau J., Hubert C., Batany J., Toupet L., Roisnel T., Hurvois J.-P., Renaud J.-L., Metal-Free Brønsted Acid Catalyzed Formal [3 + 3] Annulation. Straightforward Synthesis of Dihydro-2H-chromenones, Pyranones, and Tetrahydroquinolinones, J. Org. Chem., 74: 8963-8973 (2009).
[17] Gohain M., van Tonder J.H., Bezuidenhoudt B.C.B., Bi(OTf)3-Catalyzed Solvent-Free Synthesis of Pyrano[3,2-c]coumarins through a Tandem Addition/Annulation Reaction Between Chalcones and 4-Hydroxycoumarins, Tetrahedron Lett., 54: 3773-3776 (2013).
[18] Bagdi A.K., Majee A., Hajra A., Regioselective Synthesis of Pyrano[3,2-c]coumarins via Cu(II)-Catalyzed Tandem Reaction, Tetrahedron Lett., 54: 3892-3895 (2013).
[19] Ahmed N., Babu B.V., Efficient Route to Highly Functionalized Chalcone-Based Pyranocoumarins via Iodine-Promoted Michael Addition Followed by Cyclization of 4-Hydroxycoumarins, Synth. Commun., 43: 3044-3053 (2013).
[20] Liu Y., Zhu J., Qian J., Jiang B., Xu Z., Gold(III)-Catalyzed Tandem Conjugate Addition/Annulation of 4-Hydroxycoumarins with α,β-Unsaturated Ketones, J. Org. Chem., 76: 9096-9101 (2011).
[21] He Z., Lin X., Zhu Y., Wang Y., DDQ-Mediated Ta0ndem Synthesis of Functionalized Pyranocoumarins from 4-Hydroxycoumarins and 1,3-Diarylallylic Compounds, Heterocycles, 81: 965-976 (2010).
[22] Choi M., Heo W., Kleitz F., Ryoo R., Facile Synthesis of High Quality Mesoporous SBA-15 with Enhanced Control of the Porous Network Connectivity and Wall Thickness, Chem. Commun.,  1340-1341 (2003).
[23] Khalafi-Nezhad A., Panahi F., Phosphine-Functionalized Magnetic Nanoparticles (PFMN) as a Magnetic Recyclable Phosphorus Ligand: Preparation of its Palladium(II) Complex for Heck Reaction of Chloroarenes, J. Organomet. Chem., 741-742: 7-14 (2013).
[24] Cole A.C., Jensen J.L., Ntai I., Tran K.L.T., Weaver K.J., Forbes D.C., Davis Jr J.H., Novel Brønsted Acidic ionic Liquids and Their Use as Dual Solvent-Catalysts, J. Am. Chem. Soc., 124: 5962-5963 (2002).
[25] Jalili-Baleh L., Mohammadi N., Khoobi M., Ma’mani L., Foroumadi A., Shafiee A., Synthesis of Monospiro-2-amino-4H-pyran Derivatives Catalyzed by Propane-1-sulfonic Acid-Modified Magnetic Hydroxyapatite Nanoparticles, Helv. Chim. Acta, 96: 1601-1609 (2013).
[26] Khoobi M.,  Ma’mani L., Rezazadeh F., Zareie Z., Foroumadi A., Ramazani A., Shafiee A., One-pot Synthesis of 4H-Benzo[b]pyrans and Dihydropyrano[c]chromenes Using Inorganic-Organic Hybrid Magnetic Nanocatalyst In Water,
J. Mol. Catal. A: Chem., 359: 74-80 (2012).
[27] Hosseini-Zare M.S., Mahdavi M., Saeedi M., Asadi M., Javanshir S., Shafiee A., Foroumadi A., Synthesis of 2,3-Diaryl-5H-imidazo[2,1-a]isoindol-5-ones via the One-Pot Reaction of 1,2-Diketones, 2-Formylbenzoic Acids, and Ammonium Acetate, Tetrahedron Lett., 53: 3448-3451 (2012).
[28] Alizadeh, B.H.; Vosooghi M., Khoobi M., Javidnia A., Panah F., Safavi M., Ardestani S., Shafiee A., Synthesis and Cytotoxic Activity of Novel 9-[Hydroxy(Substitutedphenyl) Methyl]-2,2-Dimethyl-2,3,8,9-Tetrahydro-4H,10H-Pyrano [2,3-f] Chromene-4,10-Diones, Iran. J. Chem. Chem. Eng. (IJCCE), 29(4): 189-196 (2010).

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