Mostrar el registro sencillo del ítem
dc.contributor.author | Climent Olmedo, María José | es_ES |
dc.contributor.author | Corma Canós, Avelino | es_ES |
dc.contributor.author | Iborra Chornet, Sara | es_ES |
dc.contributor.author | Martí Montaner, Laura | es_ES |
dc.date.accessioned | 2016-03-30T09:12:55Z | |
dc.date.issued | 2014-04 | |
dc.identifier.issn | 1864-5631 | |
dc.identifier.uri | http://hdl.handle.net/10251/62078 | |
dc.description.abstract | 1,5-Benzothiazepines derivatives were obtained first by starting from 1,3-diphenylpropenone derivatives (chalcones) and 2-aminothiophenol by using aluminosilicate solid catalysts. However, diffusional limitations and the strong adsorption of products on the catalyst are deleterious for catalyst activity and life. Then a structured amorphous mesoporous catalyst with large pores and mild acidity that works at higher temperatures allowed us to obtain high conversions (99%) and selectivities (98%) of the desired product. A one-pot synthesis of 1,5-benzothiazepines that starts from benzaldehyde, acetophenone, and 2-aminothiophenol with 95% yield was performed by combining optimized solid base and acid catalysts in batch mode as well as in a continuous-flow reactor system. Much better conversion and selectivity as well as process intensification has been achieved with the structured mesoporous materials by avoiding intermediate and final neutralization and purification steps required in the synthesis reported previously that uses homogeneous catalysts. | es_ES |
dc.description.sponsorship | The authors acknowledge the Spanish Ministry of Education and Science for financial support in the project Consolider-Ingenio 2010 and CTQ-2011-27550. L. M. thanks the Spanish Ministry of Education and Science for a Jae-Predoc grant, co-financed by the European Social Fund Plan 2007-2013. | en_EN |
dc.language | Inglés | es_ES |
dc.publisher | Wiley-VCH Verlag | es_ES |
dc.relation.ispartof | ChemSusChem | es_ES |
dc.rights | Reserva de todos los derechos | es_ES |
dc.subject | cyclization | es_ES |
dc.subject | heterocycles | es_ES |
dc.subject | heterogeneous catalysis | es_ES |
dc.subject | mesoporous materials | es_ES |
dc.subject | multicomponent reactions | es_ES |
dc.subject.classification | QUIMICA ORGANICA | es_ES |
dc.title | Solid Catalysts for Multistep Reactions: One- Pot Synthesis of 2,3-Dihydro-1,5-benzothiazepines with Solid Acid and Base Catalysts | es_ES |
dc.type | Artículo | es_ES |
dc.embargo.lift | 10000-01-01 | |
dc.embargo.terms | forever | es_ES |
dc.identifier.doi | 10.1002/cssc.201301064 | |
dc.relation.projectID | info:eu-repo/grantAgreement/MICINN//CTQ2011-27550/ES/TRANSFORMACION CATALITICA DE BIOMASA EN DIESEL Y EN PRODUCTOS QUIMICOS/ | es_ES |
dc.rights.accessRights | Cerrado | es_ES |
dc.contributor.affiliation | Universitat Politècnica de València. Departamento de Química - Departament de Química | es_ES |
dc.contributor.affiliation | Universitat Politècnica de València. Instituto Universitario Mixto de Tecnología Química - Institut Universitari Mixt de Tecnologia Química | es_ES |
dc.description.bibliographicCitation | Climent Olmedo, MJ.; Corma Canós, A.; Iborra Chornet, S.; Martí Montaner, L. (2014). Solid Catalysts for Multistep Reactions: One- Pot Synthesis of 2,3-Dihydro-1,5-benzothiazepines with Solid Acid and Base Catalysts. ChemSusChem. 7(4):1177-1185. https://doi.org/10.1002/cssc.201301064 | es_ES |
dc.description.accrualMethod | S | es_ES |
dc.description.upvformatpinicio | 1177 | es_ES |
dc.description.upvformatpfin | 1185 | es_ES |
dc.type.version | info:eu-repo/semantics/publishedVersion | es_ES |
dc.description.volume | 7 | es_ES |
dc.description.issue | 4 | es_ES |
dc.relation.senia | 281669 | es_ES |
dc.identifier.eissn | 1864-564X | |
dc.contributor.funder | Ministerio de Ciencia e Innovación | es_ES |
dc.contributor.funder | European Social Fund | es_ES |
dc.contributor.funder | Ministerio de Educación y Ciencia | es_ES |
dc.description.references | Bariwal, J. B., Upadhyay, K. D., Manvar, A. T., Trivedi, J. C., Singh, J. S., Jain, K. S., & Shah, A. K. (2008). 1,5-Benzothiazepine, a versatile pharmacophore: A review. European Journal of Medicinal Chemistry, 43(11), 2279-2290. doi:10.1016/j.ejmech.2008.05.035 | es_ES |
dc.description.references | Wang, L., Zhang, P., Zhang, X., Zhang, Y., Li, Y., & Wang, Y. (2009). Synthesis and biological evaluation of a novel series of 1,5-benzothiazepine derivatives as potential antimicrobial agents. European Journal of Medicinal Chemistry, 44(7), 2815-2821. doi:10.1016/j.ejmech.2008.12.021 | es_ES |
dc.description.references | De Sarro, G., Chimirri, A., De Sarro, A., Gitto, R., Grasso, S., Giusti, P., & Chapman, A. G. (1995). GYKI 52466 and related 2,3-benzodiazepines as anticonvulsant agents in DBA/2 mice. European Journal of Pharmacology, 294(2-3), 411-422. doi:10.1016/0014-2999(95)00561-7 | es_ES |
dc.description.references | Ansari, F. L., Kalsoom, S., Zaheer-ul-Haq, Ali, Z., & Jabeen, F. (2011). In silico studies on 2,3-dihydro-1,5-benzothiazepines as cholinesterase inhibitors. Medicinal Chemistry Research, 21(9), 2329-2339. doi:10.1007/s00044-011-9754-6 | es_ES |
dc.description.references | N. K. Ahmed 1991 | es_ES |
dc.description.references | Org. Chem. Int. 2013 | es_ES |
dc.description.references | Pant, S., Singhal, B., Upreti, M., & Pant, U. (1998). Syntheses of 1,5-Benzothiazepines. Part 20. Syntheses of 8-Substituted-2,5-dihydro-2-(4-N-dimethylaminophenyl)-4-(4-methoxyphenyl)-1,5-benzothiazepines. Molecules, 3(8), 159-163. doi:10.3390/30600159 | es_ES |
dc.description.references | Micheli, F., Degiorgis, F., Feriani, A., Paio, A., Pozzan, A., Zarantonello, P., & Seneci, P. (2001). A Combinatorial Approach to [1,5]Benzothiazepine Derivatives as Potential Antibacterial Agents. Journal of Combinatorial Chemistry, 3(2), 224-228. doi:10.1021/cc0000949 | es_ES |
dc.description.references | Pan, X.-Q., Zou, J.-P., Huang, Z.-H., & Zhang, W. (2008). Ga(OTf)3-promoted condensation reactions for 1,5-benzodiazepines and 1,5-benzothiazepines. Tetrahedron Letters, 49(36), 5302-5308. doi:10.1016/j.tetlet.2008.06.082 | es_ES |
dc.description.references | Kodomari, M., Noguchi, T., & Aoyama, T. (2004). Solvent‐Free Synthesis of 1,5‐Benzothiazepines and Benzodiazepines on Inorganic Supports. Synthetic Communications, 34(10), 1783-1790. doi:10.1081/scc-120034159 | es_ES |
dc.description.references | Arya, K., & Dandia, A. (2008). The expedient synthesis of 1,5-benzothiazepines as a family of cytotoxic drugs. Bioorganic & Medicinal Chemistry Letters, 18(1), 114-119. doi:10.1016/j.bmcl.2007.11.002 | es_ES |
dc.description.references | Dandia, A., Sati, M., & Loupy, A. (2002). Dry-media one-pot syntheses of fluorinated-2,3-dihydro-1,5-benzothiazepines under microwave activation. Green Chemistry, 4(6), 599-602. doi:10.1039/b207004a | es_ES |
dc.description.references | Khatik, G. L., Sharma, G., Kumar, R., & Chakraborti, A. K. (2007). Scope and limitations of HClO4–SiO2 as an extremely efficient, inexpensive, and reusable catalyst for chemoselective carbon–sulfur bond formation. Tetrahedron, 63(5), 1200-1210. doi:10.1016/j.tet.2006.11.050 | es_ES |
dc.description.references | Sharma, G., Kumar, R., & Chakraborti, A. K. (2008). Fluoroboric acid adsorbed on silica-gel (HBF4–SiO2) as a new, highly efficient and reusable heterogeneous catalyst for thia-Michael addition to α,β-unsaturated carbonyl compounds. Tetrahedron Letters, 49(27), 4272-4275. doi:10.1016/j.tetlet.2008.04.144 | es_ES |
dc.description.references | Sheldon, R. A. (1996). Selective catalytic synthesis of fine chemicals: opportunities and trends. Journal of Molecular Catalysis A: Chemical, 107(1-3), 75-83. doi:10.1016/1381-1169(95)00229-4 | es_ES |
dc.description.references | Jiang, J., Jorda, J. L., Yu, J., Baumes, L. A., Mugnaioli, E., Diaz-Cabanas, M. J., … Corma, A. (2011). Synthesis and Structure Determination of the Hierarchical Meso-Microporous Zeolite ITQ-43. Science, 333(6046), 1131-1134. doi:10.1126/science.1208652 | es_ES |
dc.description.references | RODRIGUEZ, I., CLIMENT, M., IBORRA, S., FORNES, V., & CORMA, A. (2000). Use of delaminated zeolites (ITQ-2) and mesoporous molecular sieves in the production of fine chemicals: Preparation of dimethylacetals and tetrahydropyranylation of alcohols and phenols. Journal of Catalysis, 192(2), 441-447. doi:10.1006/jcat.2000.2861 | es_ES |
dc.description.references | Stephens, W., & Field, L. (1959). Notes. A Seven-Membered Heterocycle from o-Aminobenzenethiol and Chalcone. The Journal of Organic Chemistry, 24(10), 1576-1576. doi:10.1021/jo01092a610 | es_ES |
dc.description.references | Baldwin, J. E. (1976). Rules for ring closure. Journal of the Chemical Society, Chemical Communications, (18), 734. doi:10.1039/c39760000734 | es_ES |
dc.description.references | Prakash, O., Kumar, A., Sadana, A., Prakash, R., Singh, S. P., Claramunt, R. M., … Elguero, J. (2005). Study of the reaction of chalcone analogs of dehydroacetic acid and o-aminothiophenol: synthesis and structure of 1,5-benzothiazepines and 1,4-benzothiazines. Tetrahedron, 61(27), 6642-6651. doi:10.1016/j.tet.2005.03.035 | es_ES |
dc.description.references | Ried, W., & Marx, W. (1957). Über heterocyclische Siebenringsysteme, VIII. Synthesen Kondensierter 7-Gliedriger Heterocyclen mit 1 Stickstoff- und 1 Schwefelatom. Chemische Berichte, 90(11), 2683-2687. doi:10.1002/cber.19570901139 | es_ES |
dc.description.references | Climent, M. J., Corma, A., Iborra, S., & Velty, A. (2002). Catalysis Letters, 79(1/4), 157-163. doi:10.1023/a:1015364526587 | es_ES |
dc.description.references | Climent, M. J., Corma, A., & Iborra, S. (2011). Heterogeneous Catalysts for the One-Pot Synthesis of Chemicals and Fine Chemicals. Chemical Reviews, 111(2), 1072-1133. doi:10.1021/cr1002084 | es_ES |
dc.description.references | José Climent, M., Corma, A., & Iborra, S. (2012). Homogeneous and heterogeneous catalysts for multicomponent reactions. RSC Adv., 2(1), 16-58. doi:10.1039/c1ra00807b | es_ES |
dc.description.references | Climent, M. J., Corma, A., Iborra, S., & Primo, J. (1995). Base Catalysis for Fine Chemicals Production: Claisen-Schmidt Condensation on Zeolites and Hydrotalcites for the Production of Chalcones and Flavanones of Pharmaceutical Interest. Journal of Catalysis, 151(1), 60-66. doi:10.1006/jcat.1995.1008 | es_ES |
dc.description.references | CLIMENT, M. (2004). Increasing the basicity and catalytic activity of hydrotalcites by different synthesis procedures. Journal of Catalysis, 225(2), 316-326. doi:10.1016/j.jcat.2004.04.027 | es_ES |
dc.description.references | Climent, M. ., Corma, A., Iborra, S., & Velty, A. (2004). Activated hydrotalcites as catalysts for the synthesis of chalcones of pharmaceutical interest. Journal of Catalysis, 221(2), 474-482. doi:10.1016/j.jcat.2003.09.012 | es_ES |
dc.description.references | Corma, A., Fornes, V., Pergher, S. B., Maesen, T. L. M., & Buglass, J. G. (1998). Delaminated zeolite precursors as selective acidic catalysts. Nature, 396(6709), 353-356. doi:10.1038/24592 | es_ES |
dc.description.references | Emeis, C. A. (1993). Determination of Integrated Molar Extinction Coefficients for Infrared Absorption Bands of Pyridine Adsorbed on Solid Acid Catalysts. Journal of Catalysis, 141(2), 347-354. doi:10.1006/jcat.1993.1145 | es_ES |