Home Articles List Article Information
Iranian Journal of Chemistry and Chemical Engineering (IJCCE)
Journal Archive
Volume Volume 37 (2018)
Volume Volume 36 (2017)
Volume Volume 35 (2016)
Volume Volume 34 (2015)
Volume Volume 33 (2014)
Volume Volume 32 (2013)
Volume Volume 31 (2012)
Volume Volume 30 (2011)
Volume Volume 29 (2010)
Volume Volume 28 (2009)
Volume Volume 27 (2008)
Volume Volume 26 (2007)
Volume Volume 25 (2006)
Volume Volume 24 (2005)
Volume Volume 23 (2004)
Volume Volume 22 (2003)
Volume Volume 21 (2002)
Volume Volume 20 (2001)
Volume Volume 19 (2000)
Volume Volume 18 (1999)
Volume Volume 17 (1998)
Volume Volume 16 (1997)
Volume Volume 15 (1996)
Volume Volume 14 (1995)
Volume Volume 13 (1994)
Volume Volume 12 (1993)
Volume Volume 11 (1992)
Volume Volume 10 (1991)
Volume Volume 9 (1990)
Volume Volume 8 (1989)
Volume Volume 7 (1988)
Volume Volume 6 (1987)
Saeedi, M., Jeiroudi, M., Ma’mani, L., Mahdavi, M., Alipour, E., Shafiee, A., Foroumadi, A. (2015). 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. Iranian Journal of Chemistry and Chemical Engineering (IJCCE), 34(4), 39-45.
Mina Saeedi; Mohammad Jeiroudi; Leila Ma’mani; Mohammad Mahdavi; Eskandar Alipour; Abbas Shafiee; Ali Reza Foroumadi. "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". Iranian Journal of Chemistry and Chemical Engineering (IJCCE), 34, 4, 2015, 39-45.
Saeedi, M., Jeiroudi, M., Ma’mani, L., Mahdavi, M., Alipour, E., Shafiee, A., Foroumadi, A. (2015). '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', Iranian Journal of Chemistry and Chemical Engineering (IJCCE), 34(4), pp. 39-45.
Saeedi, M., Jeiroudi, M., Ma’mani, L., Mahdavi, M., Alipour, E., Shafiee, A., Foroumadi, A. 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. Iranian Journal of Chemistry and Chemical Engineering (IJCCE), 2015; 34(4): 39-45.

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

Article 3, Volume 34, Issue 4, November and December 2015, Page 39-45  XML PDF (360.66 K)
Document Type: Research Article
Authors
Mina Saeedi1; Mohammad Jeiroudi2; Leila Ma’mani3; Mohammad Mahdavi3; Eskandar Alipour2; Abbas Shafiee3; Ali Reza Foroumadi3
1Medicinal Plants Research Center, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, I.R. IRAN
2Department of Chemistry, Tehran-North Branch, Islamic Azad University, Zafar St, Tehran, I.R. IRAN
3Department 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.  
Keywords
Chalcones; Functionalized SBA-15; 4-Hydroxycoumarin; Pyrano[3; 2-c]chromenones; Supported ionic liquid
Main Subjects
Catalysts, Kinetics, Reactor; Organic Chemistry
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).

Statistics
Article View: 1,837
PDF Download: 1,644