Combustion-derived CdO nanopowder as a heterogeneous basic catalyst for efficient synthesis of sulfonamides from aromatic amines using p-toluenesulfonyl chloride

[1] Abd El-Salaam, K. M., & Hassan, E. A. (1982). Active surface centres in a heterogeneous CdO catalyst for ethanol decomposition. Surface Technology, 16, 121–128. DOI: 10.1016/0376-4583(82)90031-0. http://dx.doi.org/10.1016/0376-4583(82)90031-010.1016/0376-4583(82)90031-0Search in Google Scholar

[2] Alves, M. B., Medeiros, F. C. M., & Suarez, P. A. Z. (2010). Cadmium compounds as catalysts for biodiesel production. Industrial & Engineering Chemistry Research, 49, 7176–7182. DOI: 10.1021/ie100172u. http://dx.doi.org/10.1021/ie100172u10.1021/ie100172uSearch in Google Scholar

[3] Anderson, K. K. (1979). Sulphonic acids and their derivatives. In D. N. Jones (Ed.), Comprehensive organic chemistry (Vol. 3, pp. 345). Oxford, UK: Pergamon Press. Search in Google Scholar

[4] Angappan, S., Bechermans, L. J., & Augustin, C. O. (2004). Sintering behaviour of MgAl2O4-a prospective anode material. Materials Letters, 58, 2283–2289. DOI: 10.1016/j.matlet.2004.01.033. http://dx.doi.org/10.1016/j.matlet.2004.01.03310.1016/j.matlet.2004.01.033Search in Google Scholar

[5] Ashoka, S., Chithaiah, P., & Chandrappa, G. T. (2010). Studies on the synthesis of CdCO3 nanowires and porous CdO powder. Materials Letters, 64, 173–178. DOI: 10.1016/j.matlet.2009.10.036. http://dx.doi.org/10.1016/j.matlet.2009.10.03610.1016/j.matlet.2009.10.036Search in Google Scholar

[6] Askarinejad, A., & Morsali, A. (2008). Syntheses and characterization of CdCO3 and CdO nanoparticles by using sonochemical method. Materials Letters, 62, 478–482. DOI: 10.1016/j.matlet.2007.05.082. http://dx.doi.org/10.1016/j.matlet.2007.05.08210.1016/j.matlet.2007.05.082Search in Google Scholar

[7] Balandin, A. A., Ferapontov, V. A., & Tolstopyatova, A. A. (1960). The activity of cadmium oxide as catalyst for hydrogen dehydrogenation. Russian Chemical Bulletin, 9, 1630–1636. DOI: 10.1007/bf00906559. http://dx.doi.org/10.1007/BF0090655910.1007/BF00906559Search in Google Scholar

[8] Blin, J. L., Léonard, A., Yuan, Z. Y., Gigot, L., Vantomme, A., Cheetham, A. K., & Su, B. L. (2003). Hierarchically mesoporous/macroporous metal oxides templated from polyethylene oxide surfactant assemblies. Angewandte Chemie, 115, 2978–2981. DOI: 10.1002/ange.200250816. http://dx.doi.org/10.1002/ange.20025081610.1002/ange.200250816Search in Google Scholar

[9] Blomqvist, K., & Ebbe, R. (1984). Solution studies of systems with polynuclear complex formation. 5. Copper (II) and cadmium (II) d-(+)-tartrate systems. Inorganic Chemistry, 23, 3730–3734. DOI: 10.1021/ic00191a013. http://dx.doi.org/10.1021/ic00191a01310.1021/ic00191a013Search in Google Scholar

[10] Chan, Y.W., & Berthelette, C. ( 2002). A mild, efficient method for the synthesis of aromatic and aliphatic sulfonamides. Tetrahedron Letters, 43, 4537–4540. DOI: 10.1016/s0040-4039(02)00848-1. http://dx.doi.org/10.1016/S0040-4039(02)00848-110.1016/S0040-4039(02)00848-1Search in Google Scholar

[11] Chandrasekhar, S., & Mahapatra, S. (1998). Neighbouring group assisted sulfonamide cleavage of Sharpless aminols under acetonation conditions. Tetrahedron Letters, 39, 695–698. DOI: 10.1016/s0040-4039(97)10638-4. http://dx.doi.org/10.1016/S0040-4039(97)10638-410.1016/S0040-4039(97)10638-4Search in Google Scholar

[12] Chintareddy, V. R., & Kantam, M. L. (2011). Recent developments on catalytic applications of nano-crystalline magnesium oxide. Catalysis Surveys from Asia, 15, 89–110. DOI: 10.1007/s10563-011-9113-0. http://dx.doi.org/10.1007/s10563-011-9113-010.1007/s10563-011-9113-0Search in Google Scholar

[13] Davis, M. E. (2002). Ordered porous materials for emerging applications. Nature, 417, 813–821. DOI: 10.1038/nature00785. http://dx.doi.org/10.1038/nature0078510.1038/nature00785Search in Google Scholar

[14] Fahim, R. B., & Abd El-Salaam, K. M. (1967). Surface properties and hydration of cadmium oxide. Journal of Catalysis, 9, 63–69. DOI: 10.1016/0021-9517(67)90181-9. http://dx.doi.org/10.1016/0021-9517(67)90181-910.1016/0021-9517(67)90181-9Search in Google Scholar

[15] Gliński, M., Kijeński, J., & Jakubowski, A. (1995). Ketones from monocarboxylic acids: Catalytic ketonization over oxide systems. Applied Catalysis A: General, 128, 209–217. DOI: 10.1016/0926-860x(95)00082-8. http://dx.doi.org/10.1016/0926-860X(95)00082-810.1016/0926-860X(95)00082-8Search in Google Scholar

[16] Harter, W. G., Albrect, H., Brady, K., Caprathe, B., Dunbar, J., Gilmore, J., Hays, S., Kostlan, C. R., Lunney, B., & Walker, N. (2004). The design and synthesis of sulfonamides as caspase-1 inhibitors. Bioorganic & Medicinal Chemistry Letters, 14, 809–812. DOI: 10.1016/j.bmcl.2003.10.065. http://dx.doi.org/10.1016/j.bmcl.2003.10.06510.1016/j.bmcl.2003.10.065Search in Google Scholar PubMed

[17] Johnston, L. L., Nettleman, J. H., Braverman, M. A., Sposato, L. K., Supkowski, R. M., & LaDuca, R. L. (2010). Copper benzenedicarboxylate coordination polymers incorporating a long-spanning neutral co-ligand: Effect of anion inclusion and carboxylate pendant-arm length on topology and magnetism. Polyhedron, 29, 303–311. DOI: 10.1016/j.poly.2009.05.022. http://dx.doi.org/10.1016/j.poly.2009.05.02210.1016/j.poly.2009.05.022Search in Google Scholar

[18] Khaleel, A., & Al-Mansouri, S. (2010). Meso-macroporous γ-alumina by template-free sol-gel synthesis: The effect of the solvent and acid catalyst on the microstructure and textural properties. Colloid Surface A: Physicochemical and Engineering Aspects, 369, 272–280. DOI: 10.1016/j.colsurfa.2010.08.040. http://dx.doi.org/10.1016/j.colsurfa.2010.08.04010.1016/j.colsurfa.2010.08.040Search in Google Scholar

[19] Madhusudana Reddy, M. B., Ashoka, S., Chandrappa, G. T., & Pasha, M. A. (2010). Nano-MgO: An efficient catalyst for the synthesis of formamides from amines and formic acid under MWI. Catalysis Letters, 138, 82–87. DOI: 10.1007/s10562-010-0372-6. http://dx.doi.org/10.1007/s10562-010-0372-610.1007/s10562-010-0372-6Search in Google Scholar

[20] Madhusudana Reddy, M. B., Ashoka, S., Anandakumar, B. S., Chandrappa, G. T., & Pasha, M. A. (2011). Combustion derived nanocrystalline-ZrO2 and its catalytic activity for Biginelli condensation under microwave irradiation. Chinese Journal of Chemistry, 29, 1863–1868. DOI: 10.1002/cjoc.201180325. http://dx.doi.org/10.1002/cjoc.20118032510.1002/cjoc.201180325Search in Google Scholar

[21] Masoumeh, T., Alefeh G., Elaheh, K., & Masood, P. (2011). Two tartrate-pillared coordination polymers: Hydrothermal preparation, crystal structures, spectroscopic and thermal analyses of [M2(μ-C4H4O6)2(H2O)] · 3H2O∞ (M = Mn, Cd). Journal of Inorganic and Organometalic Polymers and Materials, 2121, 627–633 DOI: 10.1007/s10904-011-9495-5. http://dx.doi.org/10.1007/s10904-011-9495-510.1007/s10904-011-9495-5Search in Google Scholar

[22] Mazaheritehrani, M., Asghari, J., Lotfi Orimi, R., & Pahlavan, S. (2010). Microwave-assisted synthesis of nano-sized cadmium oxide as a new and highly efficient catalyst for solvent free acylation of amines and alcohols. Asian Journal of Chemistry, 22, 2554–2564. Search in Google Scholar

[23] Nagappa, B., & Chandrappa, G. T. (2007). Mesoporous nanocrystalline magnesium oxide for environmental remediation. Micropores and Mesopores Materials, 106, 212–218. DOI: 10.1016/j.micromeso.2007.02.052. http://dx.doi.org/10.1016/j.micromeso.2007.02.05210.1016/j.micromeso.2007.02.052Search in Google Scholar

[24] Nishida, H., Hamada, T., & Yonemitsu, O. (1988). Hydrolysis of tosyl esters initiated by an electron transfer from photoexcited electron-rich aromatic compounds. Journal of Organic Chemistry, 53, 3386–3387. DOI: 10.1021/jo00249a058. http://dx.doi.org/10.1021/jo00249a05810.1021/jo00249a058Search in Google Scholar

[25] Nondek, L., Vít, Z., & Málek, J. (1979). Determination of basic sites on the surface of metal oxide catalysts by desorption of benzoic acid. Reaction Kinetics and Catalysis Letters, 10, 7–11. DOI: 10.1007/bf02067504. http://dx.doi.org/10.1007/BF0206750410.1007/BF02067504Search in Google Scholar

[26] O’Connell, J. F., & Rapoport, H. (1992). 1-Benzenesulfonyland 1-p-toluenesulfonyl-3-methylimidazolium triflates: efficient reagents for the preparation of arylsulfonamides and arylsulfonates. The Journal of Organic Chemistry, 57, 4775–4777. DOI: 10.1021/jo00043a046. http://dx.doi.org/10.1021/jo00043a04610.1021/jo00043a046Search in Google Scholar

[27] Okuhara, T., & Tanaka, K. I. (1980). Intermediates of hydrogenation of conjugated dienes and of the isomerization of n-butenes on CdO catalyst. Journal of Catalysis, 61, 135–139. DOI: 10.1016/0021-9517(80)90348-6. http://dx.doi.org/10.1016/0021-9517(80)90348-610.1016/0021-9517(80)90348-6Search in Google Scholar

[28] Patil, K. C., Hegde, M. S., Rattan, T., & Aruna, S. T. (2008). Chemistry of nanocrystalline oxide materials: Combustion synthesis, properties and applications. Danvers, MA, USA: World Scientific. http://dx.doi.org/10.1142/978981279315710.1142/6754Search in Google Scholar

[29] Poissonnet, G., Théret-Bettiol, M. H., & Dodd, R. H. (1996). Preparation and 1,3-dipolar cycloaddition reactions of β-carboline azomethine ylides: A direct entry into C-1-and/or C-2-functionalized indolizino[8,7-b]indole derivatives. The Journal of Organic Chemistry, 61, 2273–2282. DOI: 10.1021/jo951520t. http://dx.doi.org/10.1021/jo951520t10.1021/jo951520tSearch in Google Scholar

[30] Reddy, N. S., Mallireddigari, M. R., Cosenza, S., Gumireddy, K., Bell, S. C., Reddy, E. P., & Reddy, M. V. R. (2004). Synthesis of new coumarin 3-(N-aryl) sulfonamides and their anticancer activity. Bioorganic & Medicinal Chemistry Letters, 14, 4093–4097. DOI: 10.1016/j.bmcl.2004.05.016. http://dx.doi.org/10.1016/j.bmcl.2004.05.01610.1016/j.bmcl.2004.05.016Search in Google Scholar PubMed

[31] Ristić, M., Popović, S., & Musić, S. (2004). Formation and properties of Cd(OH)2 and CdO particles. Materials Letters, 58, 2494–2499. DOI: 10.1016/j.matlet.2004.03.016. http://dx.doi.org/10.1016/j.matlet.2004.03.01610.1016/j.matlet.2004.03.016Search in Google Scholar

[32] Russell, M. G. N., Baker, R. J., Barden, L., Beer, M. S., Bristow, L., Broughton, H. B., Knowles, M., McAllister, G., Patel, S., & Castro, J. L. (2001). N-Arylsulfonylindole derivatives as serotonin 5-HT6 receptor ligands. Journal of Medicinal Chemistry, 44, 3881–3895. DOI: 10.1021/jm010943m. http://dx.doi.org/10.1021/jm010943m10.1021/jm010943mSearch in Google Scholar PubMed

[33] Samadi, N. S., Amat Mustajab, M. K. A., & Yacob, A. R. (2010). Activation temperature effect on the basic strength of prepared aerogel MgO (AP-MgO). International Journal of Basic & Applied Sciences, 10(2), 118–121. Search in Google Scholar

[34] Santos-Cruz, J., Torres-Delgado, G., Castanedo-Perez, R., Zúñiga-Romero, C. I., & Zelaya-Angel, O. (2007). Optical and electrical characterization of fluorine doped cadmium oxide thin films prepared by the sol-gel method. Thin Solid Films, 515, 5381–5385. DOI: 10.1016/j.tsf.2007.01.036. http://dx.doi.org/10.1016/j.tsf.2007.01.03610.1016/j.tsf.2007.01.036Search in Google Scholar

[35] Scozzafava, A., Owa, T., Mastrolorenzo, A., & Supuran, C. T. (2003). Anticancer and antiviral sulfonamides. Current Medicinal Chemistry, 10, 925–953. DOI: 10.2174/0929867033457647. http://dx.doi.org/10.2174/092986703345764710.2174/0929867033457647Search in Google Scholar

[36] Sousa, C., Pacchioni, G., & Illas, F. (1999). Ab initio study of the optical transitions of F centers at low-coordinated sites of the MgO surface. Surface Science, 429, 217–228. DOI: 10.1016/s0039-6028(99)00380-5. http://dx.doi.org/10.1016/S0039-6028(99)00380-510.1016/S0039-6028(99)00380-5Search in Google Scholar

[37] Sterrer, M., Berger, T., Diwald, O., & Knözinger, E. (2003). Energy transfer on the MgO surface, monitored by UV-induced H2 chemisorption. Journal of the American Chemical Society, 125, 195–199. DOI: 10.1021/ja028059o. http://dx.doi.org/10.1021/ja028059o10.1021/ja028059oSearch in Google Scholar PubMed

[38] Stranix, B. R., Lavallée, J. F., Sévigny, G., Yelle, J., Perron, V., LeBerre, N., Herbart, D., & Wu, J. J. (2006). Lysine sulfonamides as novel HIV-protease inhibitors: Nɛ-Acyl aromatic α-amino acids. Bioorganic & Medicinal Chemistry Letters, 16, 3459–3462. DOI: 10.1016/j.bmcl.2006.04.011. http://dx.doi.org/10.1016/j.bmcl.2006.04.01110.1016/j.bmcl.2006.04.011Search in Google Scholar PubMed

[39] Supuran, C. T., Casini, A., & Scozzafava, A. (2003). Protease inhibitors of the sulfonamide type: Anticancer, antiinflammatory, and antiviral agents. Medical Research Reviews, 23, 535–558. DOI: 10.1002/med.10047. http://dx.doi.org/10.1002/med.1004710.1002/med.10047Search in Google Scholar PubMed

[40] Thakuria, H., Borah, B. M., & Das, G. (2007). Macroporous metal oxides as an efficient heterogeneous catalyst for various organic transformations—A comparative study. Journal Molecular Catalysis A: Chemical, 274, 1–10. DOI: 10.1016/j.molcata.2007.04.024. http://dx.doi.org/10.1016/j.molcata.2007.04.02410.1016/j.molcata.2007.04.024Search in Google Scholar

[41] Waghulade, R. B., Patil, P. P., & Pasricha, R. (2007). Synthesis and LPG sensing properties of nano-sized cadmium oxide. Talanta, 72, 594–599. DOI: 10.1016/j.talanta.2006.11.024. http://dx.doi.org/10.1016/j.talanta.2006.11.02410.1016/j.talanta.2006.11.024Search in Google Scholar PubMed

[42] Yasuhara, A., Kameda, M., & Sakamoto, T. (1999). Selective monodesulfonylation of N,N-disulfonylarylamines with tetrabutylammonium fluoride. Chemical and Pharmaceutical Bulletin, 47, 809–812. http://dx.doi.org/10.1248/cpb.47.80910.1248/cpb.47.809Search in Google Scholar

[43] Yuan, W., Fearson, K., & Gelb, M. H. (1989). Synthesis of sulfur-substituted phospholipid analogs as mechanistic probes of phospholipase A2 catalysis. The Journal of Organic Chemistry, 54, 906–910. DOI: 10.1021/jo00265a034. http://dx.doi.org/10.1021/jo00265a03410.1021/jo00265a034Search in Google Scholar

[44] Yuan, Z. Y., Ren, T. Z., Vantomme, A., & Su, B. L. (2004). Facile and generalized preparation of hierarchically mesoporous-macroporous binary metal oxide materials. Chemistry of Materials, 16, 5096–5106. DOI: 10.1021/cm0494812. http://dx.doi.org/10.1021/cm049481210.1021/cm0494812Search in Google Scholar

[45] Zhang, G., Zhao, Z., Liu, J., Xu, J., Jing, Y., Duan, A., & Jiang, G. (2009). Macroporous perovskite-type complex oxide catalysts of La1−x KxCo1−y FeyO3 for diesel soot combustion. Journal of Rare Earths, 27, 955–960. DOI: 10.1016/s1002-0721(08)60369-5. http://dx.doi.org/10.1016/S1002-0721(08)60369-510.1016/S1002-0721(08)60369-5Search in Google Scholar

[46] Zheng, Y. Q., Lin., J. L., & Kong, Z. P. (2004). Coordination polymers based on cobridging of rigid and flexible spacer ligands: Syntheses, crystal structures, and magnetic properties of [Mn(bpy)(H2O)(C4H4O4)]·0.5bpy, Mn(bpy)(C5H6O4), and Mn(bpy)(C6H8O4). Inorganic Chemistry, 43, 2590–2596. DOI: 10.1021/ic0301268. http://dx.doi.org/10.1021/ic030126810.1021/ic0301268Search in Google Scholar PubMed

[47] Zheng, Y. Q., Han, X. Y., & Zhu, H. L. (2010). Syntheses, crystal structures and properties of tetrahydrofuran-2,3,4,5-tetracarboxylato bridged copper(II) coordination polymers with alkali metals. Polyhedron, 29, 911–919. DOI: 10.1016/j.poly.2009.10.022. http://dx.doi.org/10.1016/j.poly.2009.10.02210.1016/j.poly.2009.10.022Search in Google Scholar