Green Synthesis of Pyrazol‑chromeno[2,3‑d]pyrimidinones Using SBA-Pr-SO3H as an Efficient Nanocatalyst

Document Type: Research Article

Authors

1 Department of Chemistry, Alzahra University, P.O. Box 1993893973 Tehran, I.R. IRAN

2 School of Chemistry, College of Science, University of Tehran, P.O. Box 14155-6455 Tehran, I.R. IRAN

3 Research Institute of Petroleum, Shahid Beheshti University Branch, Academic Center for Education, Culture & Research, Tehran, I.R. IRAN

Abstract

Hexagonal mesoporous silica (SBA-15) was prepared and then functionalized by(3-mercaptopropyl)trimethoxysilane. The obtained 3-mercaptopropyl functionalized SBA-15 (SBA-Pr-SH) was then oxidized using H2O2 in methanol under an acidic condition to give sulfonic acid functionalized mesoporous silica (SBA-Pr-SO3H). The latter was characterized using different techniques (including TGA, BET, BJH, CHN, SEM, and TEM) and then used as a catalyst in organic synthesis. In the next step, SBA-Pr-SO3H catalyzed the three-component reaction of pyrazolone, salicylaldehydes, and barbituric acid in water under reflux condition. Through this procedure various pyrazolchromeno[2,3-d]pyrimidinone derivatives were obtained. The reaction conditions were completely green due to the use of water as a solvent and the presence of an environmentally benign catalyst.

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[1] Tojino M., Ryu I. "Multicomponent Reactions" Wiley-VCH, Weinheim, Germany (2005).

[2] Newton D.W., Kluza R.B., pKa Values of Medicinal Compounds in Pharmacy Practice, Ann. Pharmacother., 12(9): 546-554 (1978).

[3] Wiley R.H., Wiley P.F. "Pyrazolones, Pyrazolidones, and Derivatives" Wiley-Interscience (1964).

[4] Madhu N., Radhakrishnan P., Grunert M., Weinberger P., Linert W., Antipyrine and Its Derivatives with First Row Transition Metals, Rev. Inorg. Chem., 23(1): 1-24 (2003).

[5] Bamoniri A., Mirjalili B.F., Jafari A.A., Abasaltian F., Synthesis of 1,3,5-tri-Substituted Pyrazoles Promoted by P2O5.SiO2, Iran. J. Catal., 2(2): 75-78 (2012).

[6] Kees K., Fitzgerald J., Steiner K., Mattes J., Mihan B., Tosi T., Mondoro D., McCaleb M., New Potent Antihyperglycemic Agents in db/db Mice: Synthesis and Structure−Activity Relationship Studies of
(4-substituted benzyl)(trifluoromethyl)pyrazoles and -Pyrazolones
, J. Med. Chem., 39: 3920-3928 (1996).

[7] Singh P., Paul K., Holzer W., Synthesis of Pyrazole-Based Hybrid Molecules: Search for Potent Multidrug Resistance Modulators, Bioorg. Med. Chem., 14(14): 5061-5071 (2006).

[8] Lashgari N., Badiei A., Mohammadi Ziarani G., Modification of Mesoporous Silica SBA-15 with Different Organic Molecules to Gain Chemical Sensors: A Review, Nanochem. Res., 1(1): 127-141 (2016).

[9] Beck J., Vartuli J., Roth W.J., Leonowicz M., Kresge C., Schmitt K., Chu C., Olson D.H., Sheppard E., McCullen S., A New Family of Mesoporous Molecular Sieves Prepared with Liquid Crystal Templates, J. Am. Chem. Soc., 114(27): 10834-10843 (1992).

[10] Zhao D., Feng J., Huo Q., Melosh N., Fredrickson G.H., Chmelka B.F., Stucky G.D., Triblock Copolymer Syntheses of Mesoporous Silica with Periodic 50 to 300 Angstrom Pores, Science, 279(5350): 548-552 (1998).

[11] Zhao D., Yang P., Melosh N., Feng J., Chmelka B.F., Stucky G.D., Continuous Mesoporous Silica Films with Highly Ordered Large Pore Structures, Adv. Mater., 10(16): 1380-1385 (1998).

[12] Bahrami K., Khodaei M.M., Fattahpour P., SBA-15-Pr–SO3H as Nanoreactor Catalyzed Oxidation of Sulfides Into Sulfoxides, Catal. Sci. Tech., 1(3): 389-393 (2011).

[13] Mohammadi Ziarani G., Hassanzadeh Z., Gholamzadeh P., Asadi S., Badiei A., Advances in Click Chemistry for Silica-Based Material Construction, RSC Adv., 6(26): 21979-22006 (2016).

[14] Kim K.B., Kim H., Song E.J., Kim S., Noh I., Kim C., A Cap-Type Schiff Base Acting as a Fluorescence Sensor for Zinc (II) and a Colorimetric Sensor for Iron (II), Copper (II), and Zinc (II) in Aqueous Media, Dalton Trans., 42(47): 16569-16577 (2013).

[15] Hajiaghababaei L., Abozari S., Badiei A., Zarabadi Poor P., Dehghan Abkenar S., Ganjali M.R., Mohammadi Ziarani G., Amino Ethyl-Functionalized SBA-15: a Promising Adsorbent for Anionic and Cationic Dyes Removal, Iran. J. Chem. Chem. Eng. (IJCCE), 36(1): 97-108 (2017).

[16] Hu Q., Li J.J., Hao Z.P., Li L.D., Qiao S.Z., Dynamic Adsorption of Volatile Organic Compounds on Organofunctionalized SBA-15 Materials, Chem. Eng. J., 149(1): 281-288 (2009).

[17] Mohammadi Ziarani G., Ghorbi S., Gholamzadeh P., Badiei A., Application of SBA-Pr-SO3H as a Solid Acid Nanoreactor in the Biginelli Reaction, Iran. J. Catal., 6(6): 229-235 (2016).

[18] Gholamzadeh P., Mohammadi Ziarani G., Zandi F., Soorki, A.A., Badiei A., Yazdian F., Modification of Fumed Silica Surface with Different Sulfonamides via a Postsynthesis Method and Their Application as Antibacterial Agents, C. R. Chim., 20(8): 833-840 (2017)

[19] Gholamzadeh P., Mohammadi Ziarani G., Badiei A.R., Immobilization of Lipases onto the SBA-15 Mesoporous Silica, Biocatal. Biotransform., 35(3): 131-150 (2017),

[20] Mohammadi Ziarani G., Aleali F., Lashgari N., Badiei A., An Efficient Green Approach for the Synthesis of Structurally Diversified Spirooxindoles Using Sulfonic Acid Functionalized Nanoporous Silica (SBA-Pr-SO3H), Iran. J. Chem. Chem. Eng. (IJCCE), 35(1): 17-23 (2016).

[21] Afsar S.Y., Mohammadi Ziarani G., Mollabagher H., Gholamzadeh P., Badiei A., Soorki A.A., Application of SBA-Pr-SO3H in the Synthesis of 2,3-dihydroquinazoline-4(1H)-ones: Characterization, UV–Vis Investigations and DFT Studies, Res. Chem. Intermed., 14(3): 577–583 (2017).

[22] Gholamzadeh P., Mohammadi Ziarani G., Lashgari N., Badiei A., Shayesteh A., Jafari M., A Simple Colorimetric Chemosensor for Naked Eye Detection of Cyanide Ion, J. Fluoresc., 26(5): 1857–1864 (2016).

[23] Gholamzadeh P., Mohammadi Ziarani G., Badiei A., Application of SBA-Pr-SO3H in the Green Synthesis of Isatinhydrazone Derivatives: Their Characterization, J. Chil. Chem. Soc., 61(2): 2935-2939 (2016).

[24] Mohammadi Ziarani G., Hassanzadeh Z., Gholamzadeh P., Abolhassani Soorki A., A Rapid, Green, and Efficient Microwave-Assisted Synthesis and Antimicrobial Evaluation of Spiroindeno[1,2-b]pyrido[2,3-d]pyrimidine-5,3'-indoline Derivatives, Rev. Roum. Chim., 61(2): 77-81 (2016).

[25] Ahmadi T., Mohammadi Ziarani G., Gholamzadeh P., Mollabagher H., Recent Advances in Asymmetric Multicomponent Reactions, Tetrahedron Asymmetry, 28(5): 708-724 (2017).

[26] Mohammadi Ziarani G., Hosseini Nasab N., Rahimifard M., Abolhasani Soorki A., One-pot Synthesis of Pyrido[2,3-d]pyrimidine Derivatives Using Sulfonic Acid Functionalized SBA-15 and the Study on Their Antimicrobial Activities, J. Saudi Chem. Soc., 19(6): 676-681 (2015).

[27] Mohammadi Ziarani G., Hosseini Nasab N. Rahimifard M., Badiei A., Soorki A.A., Synthesis of Dihydropyrido[2,3-d]pyrimidine Derivatives in the Presence of Sulfonic Acid Functionalized SBA-15 and the Study of Their Antimicrobial Activities, Sci. Iran. Trans. C, 22(6): 2319-2325 (2015).

[28] Mohammadi Ziarani G., Lashgari N., Badiei A., Sulfonic Acid-Functionalized Mesoporous Silica (SBA-Pr-SO3H) as Solid Acid Catalyst in Organic Reactions, J. Mol. Catal. A: Chem., 397: 166-191 (2015).

[29] Gholamzadeh P., Mohammadi Ziarani G., Badiei A., Bahrami Z., Application of Sulfonic acid Functionalized Nanoporous Silica (SBA-Pr-SO3H) in the Solvent Free Synthesis of (E)-arylidene-1,3-dihydroindole-2-ones, Eur. J. Chem., 3(3): 279-282 (2012).

[30] Deruiter J., Carter D.A., Arledge W.S., Sullivan P.J., Synthesis and Reactions of 4‐isopropylidene‐1‐ aryl‐3‐methyl‐2‐pyrazolin‐5‐ones, J. Heterocycl. Chem., 24(1): 149-153 (1987).

[31] Jing L., Wang L., Zhao Y., Tan R., Xing X., Liu T., Huang W., Luo Y., Li Z., Synthesis, Crystal Structure and Evaluation of Cancer Inhibitory Activity of 4-[indol-3-yl-methylene]-1H-pyrazol-5(4H)-one Derivatives. J. Chem. Res., 36(12): 691-696 (2012).

[32] Bormasheva K., Nechaeva O., Moiseev I., Reactions of Adamantyl-substituted Keto Esters with Hydrazine and Phenylhydrazine, Russ. J. Org. Chem., 44(12): 1760-1764 (2008).

[33] Soleimani E., Ghanbarian M., Saei P., Taran M., Synthesis of New Derivatives of Pyrazol-Chromeno[2,3-d]pyrimidine-ones by a One-Pot Three-Component Reaction, J. Iran. Chem. Soc., 12(12): 2227-2232 (2015).

[34] Zhao D., Huo Q., Feng J., Chmelka B.F., Stucky G.D., Nonionic Triblock and Star Diblock Copolymer and Oligomeric Surfactant Syntheses of Highly Ordered, Hydrothermally Stable, Mesoporous Silica Structures, J. Am. Chem. Soc., 120(24): 6024-6036 (1998).

[35] Mohammadi Ziarani G., Badiei A.R., Khaniania Y., Haddadpour M., One Pot Synthesis of Polyhydroquinolines Catalyzed by Sulfonic Acid Functionalized SBA-15 as a New Nanoporous Acid Catalyst under Solvent Free Conditions, Iran. J. Chem. Chem. Eng. (IJCCE), 29(2): 1-10 (2010).