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dc.contributor.author | Abonia, Rodrigo | - |
dc.contributor.author | C. García, Andres | - |
dc.date.accessioned | 2022-11-03T23:37:55Z | - |
dc.date.available | 2022-11-03T23:37:55Z | - |
dc.date.issued | 2021-12-13 | - |
dc.identifier.issn | 0370-3908 | spa |
dc.identifier.uri | https://repositorio.accefyn.org.co/handle/001/2019 | - |
dc.description.abstract | Los productos de Knoevenagel diversamente sustituidos se sometieron a reducción con NaBH4 en una solución de MeOH/dioxano a 70 oC. En todos los casos se consiguió una reducción selectiva de su doble enlace C=C. Las condiciones de reducción toleraron una variedad de grupos funcionales, aunque los productos aldólicos simples o Claisen-Schmidt mostraron ser menos selectivos hacia la reducción C=C y, por el contrario, el enlace C=O se redujo en estas condiciones de reacción. Además, la selectividad de la reducción química mediada por NaBH4 se comparó con la hidrogenación catalítica mediada por Raney-Nickel clásica para encontrar similitudes y diferencias. Además, al tratar de explicar el proceso reductor selectivo mediado por NaBH4, se propuso una vía mecanicista plausible a este respecto. | spa |
dc.description.abstract | Diversely substituted Knoevenagel products were subjected to reduction with NaBH4 in MeOH/pdioxane solution at 70 oC. Selectively reduction of their C=C double bond was achieved in all cases. Reduction conditions tolerated a variety of functional groups although simple aldolic or Claisen-Schmidt products showed to be less selective toward C=C reduction and on the contrary C=O bond was reduced under these reaction conditions. Additionally, selectivity of the NaBH4-mediated chemical reduction was compared with the classical Raney-Nickel-mediated catalytic hydrogenation in order to find similarities and differences. Moreover, trying to explain the selective NaBH4-mediated reductive process a plausible mechanistic pathway was proposed in this regard. | eng |
dc.format.mimetype | application/pdf | spa |
dc.language.iso | eng | spa |
dc.publisher | Revista de la Academia Colombiana de Ciencias Exactas, Físicas y Naturales | spa |
dc.rights.uri | https://creativecommons.org/licenses/by-nc-sa/4.0/ | spa |
dc.title | Uso de una mezcla tibia de dioxano/MeOH/NaBH4 como medio conveniente para la reducción química selectiva del doble enlace C=C en sistemas α,β-insaturados | spa |
dc.title | Using a warm dioxane/MeOH/NaBH4 mixture as convenient medium for the selective chemical reduction of the C=C double bond in α,β-unsaturated systems | eng |
dc.type | Artículo de revista | spa |
dcterms.audience | Estudiantes, Profesores, Comunidad científica. | spa |
dcterms.references | Aramini, A., Brinchi, L., Germani, R., Savelli, G. (2000). Reductions of α,β‐unsaturated ketones by NaBH4 or NaBH4 + CoCl2: Selectivity control by water or by aqueous micellar solutions. Eur. J. Org. Chem. 2000: 1793-1797. doi.org/10.1002/(SICI)1099-690(200005)2000:9<1793::AIDEJOC1793>3.0.CO;2-A | spa |
dcterms.references | Balcells, D., Clot, E., Eisenstein, O., Nova, A., Perrin, L. (2016). Deciphering selectivity in organic reactions: A multifaceted problem. Acc. Chem. Res. 49: 1070-1078. doi: 10.1021/acs.accounts.6b00099 | spa |
dcterms.references | Cai, Q., Sheng, H.-Y., Li, D.-K., Liu, Y., Wu, A.-X. (2018). Base-promoted tandem cyclization for the synthesis of polyfunctional 2-hydroxy-,3-dihydrofurans from arylglyoxal monohydrates and 3-(1H-indol-3-yl)-3-oxopropanenitrile. Synlett. 29: 1926-1932. doi: 10.1055/s-0037-1609555 | spa |
dcterms.references | Chen, T., Xu, X.‐P., Ji, S.‐J. (2013). Facile and efficient synthesis of indol‐3‐yl substituted pyran derivatives via one‐pot multicomponent reactions under ultrasonic irradiation. J. Heterocycl. Chem. 50: 244-251. doi.org/10.1002/jhet.983 | spa |
dcterms.references | Chikashita, H., Nishida, S., Miyazaki, M., Morita, Y., Itoh, K. (1987). In situ generation and synthetic application of 2-henylbenzimidazoline to the selective reduction of carbon–carbon double bonds of electron-deficient olefins. Bull. Chem. Soc. Jpn. 60: 737-746. doi. org/10.1246/bcsj.60.737 | spa |
dcterms.references | Cornubert, R. & Eggert, H.G. (1954). Bull. Soc. Chim. Fr. 21: 522-523. | spa |
dcterms.references | Cornubert, R. & Thomas, P. (1954). Bull. Soc. Chim. Fr. 21: 524-528. | spa |
dcterms.references | Fadda, A.A., El-Mekabaty, A., Mousa, I.A., Elattar, K.M. (2014). Chemistry of 3-(1H-indol-3-yl)-3-oxopropanenitrile. Synth. Commun. 44:1579-1599. doi.org/10.1080/00397911.2013.861915 | spa |
dcterms.references | Felpin, F.-X. & Fouquet, E. (2010). A useful, reliable and safer protocol for hydrogenation and the hydrogenolysis of O‐benzyl groups: The in situ preparation of an active Pd0/C catalyst with | spa |
dcterms.references | well‐defined properties. Chem. Eur. J. 16: 12440–12445. doi.org/10.1002/chem.201001377 Gutierrez, M., Nazareno, M.A., Sosa, V., López de Mishima, B.A., Mishima, H.T. (2010). | spa |
dcterms.references | Hydrogenation of chalcones using hydrogen permeating through a Pd and palladized Pd electrodes. Electrochim. Acta. 55: 5831–5839. doi.org/10.1016/j.electacta.2010.05.032 | spa |
dcterms.references | Hammond, C.N., Schatz, P.F., Davidson, T.A. (2009). Synthesis and hydrogenation of disubstituted chalcones. A guided-inquiry organic chemistry project. J. Chem. Educ. 86: 234-239. doi.org/10.1021/ed086p234 | spa |
dcterms.references | Inoue, K., Ishida, T., Shibata, I., Baba, A. (2002). Remarkable dependence of diastereoselectivity on anhydrous or aqueous solvent in the indium hydride promoted reductive aldol reaction of α,β‐unsaturated ketones. Adv. Synth. Catal. 344: 283-287. doi.org/10.1002/1615-4169(200206)344:3/4<283::AID-ADSC283>3.0.CO;2-S | spa |
dcterms.references | Insuasty, B., Ramírez, J., Becerra, D., Echeverry, C., Quiroga, J., Abonia, R., Robledo, S.M., Vélez, I.D., Upegui, Y., Munoz, J.A., Ospina, V., Nogueras, M., Cobo, J. (2015). An efficient synthesis of new caffeine-based chalcones, pyrazolines and pyrazolo[3,4-b][1,4] diazepines as potential antimalarial, antitrypanosomal and antileishmanial agents. Eur. J. Med. Chem. 93: 401-413. doi.org/10.1016/j.ejmech.2015.02.040 | spa |
dcterms.references | Insuasty, D., Robledo, S.M., Vélez, I.D., Cuervo, P., Insuasty, B., Quiroga, J., Nogueras, M., Cobo, J., Abonia, R. (2017). A Schmidt rearrangement-mediated synthesis of novel tetrahydro-benzo[1,4]diazepin-5-ones as potential anticancer and antiprotozoal agents. Eur. J. Med. Chem. 141: 567-583. doi.org/10.1016/j.ejmech.2017.10.024 | spa |
dcterms.references | Keess, S. & Oestreich, M. (2017). Access to fully alkylated germanes by B(C6F5)3-catalyzed transfer hydrogermylation of alkenes. Org. Lett. 19: 1898-1901. doi.org/10.1021/acs.orglett.7b00672 | spa |
dcterms.references | Kong, A., Han, X., Lu, X. (2006). Highly efficient construction of benzene ring in carbazoles by palladium-catalyzed endo-mode oxidative cyclization of 3-(3‘-alkenyl)indoles. Org. Lett. 8: 1339-1342. doi.org/10.1021/ol060039u | spa |
dcterms.references | Lipshutz, B.H., Keith, J., Papa, P., Vivian, R. (1998). A convenient, efficient method for conjugate reductions using catalytic quantities of Cu(I). Tetrahedron Lett. 39: 4627-4630. doi.org/10.1016/S0040-4039(98)00855-7 | spa |
dcterms.references | Mohamadi, M., Setamdideh, D., Khezri, B. (2013). Regioselective and chemoselective reduction of Ramírez-Prada, J., Robledo, S.M., Vélez, D., Crespo, M.P., Quiroga, J., Abonia, R., Montoya, A., Svetaz, L., Zacchino, S., Insuasty, B. (2017). Synthesis of novel quinoline–based 4,5–dihydro–1H–pyrazoles as potential anticancer, antifungal, antibacterial and antiprotozoal agents. Eur. J. Med. Chem. 131: 237-254. doi.org/10.1016/j.ejmech.2017.03.016 | spa |
dcterms.references | Tucker, S.H. (1950). Catalytic hydrogenation using Raney nickel. J. Chem. Educ. 27: 489-493. | spa |
dcterms.references | Wang, Q.-D., Yang, J.-M., Fang, D., Ren, J., Dong, B., Zhou, B., Zeng, B.-B. (2016). Chemoselective Cu (I) catalyzed bis (pinacolato) diboron conjugate addition and reduction onto α,β-unsaturated carbonyl compounds. Tetrahedron Lett. 57: 2587-2590. doi.org/10.1016/j.tetlet.2016.04.094 | spa |
dcterms.references | Ward, R.S. (1999). In Selectivity in organic synthesis, 1st Edition, Wiley eds,. ISBN: 978-0-471-98779-6 | spa |
dcterms.references | Zeynizadeh, B. & Shirini, F. (2003). Mild and efficient reduction of α,β-unsaturated carbonyl compounds, α-diketones and acyloins with sodium borohydride/Dowex1-x8 system. Bull. Korean Chem. Soc. 24: 295-298. doi.org/10.5012/bkcs.2003.24.3.295 | spa |
dcterms.references | Zheng, H.-X., Xiao, Z.-F., Yao, C.-Z., Li, Q.-Q., Ning, X.-S., Kang, Y.-B., Tang, Y. (2015). Transition-metal-free self-hydrogen-transferring allylic isomerization. Org. Lett. 17: 6102-6105. doi.org/10.1021/acs.orglett.5b03124 | spa |
dc.rights.accessrights | info:eu-repo/semantics/openAccess | spa |
dc.type.driver | info:eu-repo/semantics/article | spa |
dc.type.version | info:eu-repo/semantics/updatedVersion | spa |
dc.rights.creativecommons | Atribución-NoComercial-CompartirIgual 4.0 Internacional (CC BY-NC-SA 4.0) | spa |
dc.identifier.doi | https://doi.org/10.18257/raccefyn.1465 | - |
dc.subject.proposal | Chalcones | spa |
dc.subject.proposal | Chalcones | eng |
dc.subject.proposal | Knoevenagel productos | spa |
dc.subject.proposal | Knoevenagel products | eng |
dc.subject.proposal | Sistemas α,β-insaturados | spa |
dc.subject.proposal | α,β-Unsaturated systems | eng |
dc.subject.proposal | Reducciones selectivas | spa |
dc.subject.proposal | Selective reductions | eng |
dc.subject.proposal | Reducciones mediadas por NaBH4 | spa |
dc.subject.proposal | NaBH4-mediate reductions | eng |
dc.subject.proposal | Hidrogenación catalítica | spa |
dc.subject.proposal | Catalytic hydrogenation | eng |
dc.type.coar | http://purl.org/coar/resource_type/c_2df8fbb1 | spa |
dc.relation.ispartofjournal | Revista de la Academia Colombiana de Ciencias Exactas, Físicas y Naturales | spa |
dc.relation.citationvolume | 45 | spa |
dc.relation.citationstartpage | 1232 | spa |
dc.relation.citationendpage | 1245 | spa |
dc.contributor.corporatename | Academia Colombiana de Ciencias Exactas, Físicas y Naturales | spa |
dc.identifier.eissn | 2382-4980 | spa |
dc.relation.citationissue | 177 | spa |
dc.type.content | Text | spa |
dc.type.redcol | http://purl.org/redcol/resource_type/ART | spa |
oaire.accessrights | http://purl.org/coar/access_right/c_abf2 | spa |
oaire.version | http://purl.org/coar/version/c_970fb48d4fbd8a85 | spa |
Appears in Collections: | BB. Boletín Electrónico de la Academia Colombiana de Ciencias Exactas, Físicas y Naturales |
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