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Cycloreversion of beta-lactams via photoinduced electron transfer

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Cycloreversion of beta-lactams via photoinduced electron transfer

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dc.contributor.author Pérez Ruiz, Raul es_ES
dc.contributor.author Sáez Cases, José Antonio es_ES
dc.contributor.author Jiménez Molero, María Consuelo es_ES
dc.contributor.author Miranda Alonso, Miguel Ángel es_ES
dc.date.accessioned 2016-04-01T10:55:11Z
dc.date.available 2016-04-01T10:55:11Z
dc.date.issued 2014-11-14
dc.identifier.issn 1477-0520
dc.identifier.uri http://hdl.handle.net/10251/62110
dc.description.abstract The radical anions of beta-lactams, photogenerated in the presence of DABCO as an electron donor, undergo cycloreversion via N-C4 bond cleavage, back electron transfer and final C2-C3 bond cleavage, leading to olefins. The involved intermediates are 1,4-radical anions and 1,4-biradicals. The experimental observations are consistent with the results of DFT calculations. es_ES
dc.description.sponsorship Financial support from the Spanish Government (CTQ2013-47872-C2-1-P, SEV-2012-0267, BES-2011-043706, JCI-2010-06204), from CSIC (JAEDOC 101-2011 co-funded by FSE) and from the Generalitat Valenciana (PROMETEOII/2013/005) is gratefully acknowledged. J. A. S. acknowledges the computational facilities provided by the Theoretical Computational Chemistry Group of Prof. L. R. Domingo at the Universitat de Valencia. en_EN
dc.language Inglés es_ES
dc.publisher Royal Society of Chemistry es_ES
dc.relation.ispartof Organic and Biomolecular Chemistry es_ES
dc.rights Reserva de todos los derechos es_ES
dc.subject PHOTOCHEMICAL-REACTIONS es_ES
dc.subject MILLENNIUM es_ES
dc.subject KINETICS es_ES
dc.subject.classification QUIMICA ORGANICA es_ES
dc.title Cycloreversion of beta-lactams via photoinduced electron transfer es_ES
dc.type Artículo es_ES
dc.identifier.doi 10.1039/c4ob01416b
dc.relation.projectID info:eu-repo/grantAgreement/MINECO//CTQ2013-47872-C2-1-P/ES/METABOLITOS FOTOACTIVOS/ / es_ES
dc.relation.projectID info:eu-repo/grantAgreement/CSIC//JAEDOC 101-2011/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/GVA//PROMETEOII%2F2013%2F005/ES/ESPECIES FOTOACTIVAS Y SU INTERACCION CON BIOMOLECULAS/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/MICINN//JCI-2010-06204/ES/JCI-2010-06204/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/MICINN//BES-2011-043706/ES/BES-2011-043706/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/MINECO//SEV-2012-0267/ES/SEV-2012-0267/ es_ES
dc.rights.accessRights Abierto 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 Pérez Ruiz, R.; Sáez Cases, JA.; Jiménez Molero, MC.; Miranda Alonso, MÁ. (2014). Cycloreversion of beta-lactams via photoinduced electron transfer. Organic and Biomolecular Chemistry. 12(42):8428-8432. https://doi.org/10.1039/c4ob01416b es_ES
dc.description.accrualMethod S es_ES
dc.relation.publisherversion http://dx.doi.org/10.1039/c4ob01416b es_ES
dc.description.upvformatpinicio 8428 es_ES
dc.description.upvformatpfin 8432 es_ES
dc.type.version info:eu-repo/semantics/publishedVersion es_ES
dc.description.volume 12 es_ES
dc.description.issue 42 es_ES
dc.relation.senia 288000 es_ES
dc.identifier.eissn 1477-0539
dc.contributor.funder Generalitat Valenciana es_ES
dc.contributor.funder Consejo Superior de Investigaciones Científicas es_ES
dc.contributor.funder European Social Fund es_ES
dc.description.references Von Nussbaum, F., Brands, M., Hinzen, B., Weigand, S., & Häbich, D. (2006). Antibacterial Natural Products in Medicinal Chemistry—Exodus or Revival? Angewandte Chemie International Edition, 45(31), 5072-5129. doi:10.1002/anie.200600350 es_ES
dc.description.references β-Lactams in the New Millennium. Part-I: Monobactams and Carbapenems. (2004). Mini-Reviews in Medicinal Chemistry, 4(1), 69-92. doi:10.2174/1389557043487501 es_ES
dc.description.references β-Lactams in the New Millennium. Part-II: Cephems, Oxacephems, Penams and Sulbactam. (2004). Mini-Reviews in Medicinal Chemistry, 4(1), 93-109. doi:10.2174/1389557043487547 es_ES
dc.description.references Buynak, J. (2004). The Discovery and Development of Modified Penicillin- and Cephalosporin- Derived β-Lactamase Inhibitors. Current Medicinal Chemistry, 11(14), 1951-1964. doi:10.2174/0929867043364847 es_ES
dc.description.references Veinberg, G., Vorona, M., Shestakova, I., Kanepe, I., & Lukevics, E. (2003). Design of β-Lactams with Mechanism Based Nonantibacterial Activities. Current Medicinal Chemistry, 10(17), 1741-1757. doi:10.2174/0929867033457089 es_ES
dc.description.references Chemistry and Biology of β-Lactam Antibiotics , ed. R. B. Morin and M. Gorman , Academic Press , New York , 1982 , pp. 1–3 es_ES
dc.description.references Nathwani, D., & Wood, M. J. (1993). Penicillins. Drugs, 45(6), 866-894. doi:10.2165/00003495-199345060-00002 es_ES
dc.description.references Fischer, M. (1968). Photochemische Reaktionen, IV. Photochemische Fragmentierungen von β-Lactamen. Chemische Berichte, 101(8), 2669-2678. doi:10.1002/cber.19681010809 es_ES
dc.description.references Fabre, H., Ibork, H., & Lerner, D. A. (1994). Photoisomerization Kinetics of Cefuroxime Axetil and Related Compounds. Journal of Pharmaceutical Sciences, 83(4), 553-558. doi:10.1002/jps.2600830422 es_ES
dc.description.references Rossi, E., Abbiati, G., & Pini, E. (1999). Substituted 1-benzyl-4-(benzylidenimino)-4-phenylazetidin-2-ones: Synthesis, thermal and photochemical reactions. Tetrahedron, 55(22), 6961-6970. doi:10.1016/s0040-4020(99)00325-7 es_ES
dc.description.references Gómez-Gallego, M., Alcázar, R., Ramírez, P., Vincente, R., J. Mancheño, M., & A. Sierra, M. (2001). A Study of the Photochemical Isomerization in b-Lactam Rings. HETEROCYCLES, 55(3), 511. doi:10.3987/com-00-9127 es_ES
dc.description.references MUKERJEE, A. K., & SINGH, A. K. (1975). Reactions of Natural and Synthetic β-Lactams. Synthesis, 1975(09), 547-589. doi:10.1055/s-1975-23842 es_ES
dc.description.references Mukerjee, A. K., & Singh, A. K. (1978). β-Lactams: retrospect and prospect. Tetrahedron, 34(12), 1731-1767. doi:10.1016/0040-4020(78)80209-9 es_ES
dc.description.references Pérez-Ruiz, R., Jiménez, M. C., & Miranda, M. A. (2014). Hetero-cycloreversions Mediated by Photoinduced Electron Transfer. Accounts of Chemical Research, 47(4), 1359-1368. doi:10.1021/ar4003224 es_ES
dc.description.references Pérez-Ruiz, R., Sáez, J. A., Domingo, L. R., Jiménez, M. C., & Miranda, M. A. (2012). Ring splitting of azetidin-2-ones via radical anions. Organic & Biomolecular Chemistry, 10(39), 7928. doi:10.1039/c2ob26528a es_ES
dc.description.references Rehm, D., & Weller, A. (1970). Kinetics of Fluorescence Quenching by Electron and H-Atom Transfer. Israel Journal of Chemistry, 8(2), 259-271. doi:10.1002/ijch.197000029 es_ES
dc.description.references Kavarnos, G. J., & Turro, N. J. (1986). Photosensitization by reversible electron transfer: theories, experimental evidence, and examples. Chemical Reviews, 86(2), 401-449. doi:10.1021/cr00072a005 es_ES
dc.description.references Gandon, V., Bertus, P., & Szymoniak, J. (2000). A Straightforward Synthesis of Cyclopropanes from Aldehydes and Ketones. European Journal of Organic Chemistry, 2000(22), 3713-3719. doi:10.1002/1099-0690(200011)2000:22<3713::aid-ejoc3713>3.0.co;2-1 es_ES
dc.description.references Wang, S. C., Troast, D. M., Conda-Sheridan, M., Zuo, G., LaGarde, D., Louie, J., & Tantillo, D. J. (2009). Mechanism of the Ni(0)-Catalyzed Vinylcyclopropane−Cyclopentene Rearrangement. The Journal of Organic Chemistry, 74(20), 7822-7833. doi:10.1021/jo901525u es_ES
dc.description.references Kashima, C., Fukusaka, K., & Takahashi, K. (1997). Synthesis of optically active β-lactams by the reaction of 2-acyl-3-phenyl-l-menthopyrazoles with CN compounds. Journal of Heterocyclic Chemistry, 34(5), 1559-1565. doi:10.1002/jhet.5570340529 es_ES
dc.description.references Andreu, I., Delgado, J., Espinós, A., Pérez-Ruiz, R., Jiménez, M. C., & Miranda, M. A. (2008). Cycloreversion of Azetidines via Oxidative Electron Transfer. Steady-State and Time-Resolved Studies. Organic Letters, 10(22), 5207-5210. doi:10.1021/ol802181u es_ES
dc.description.references Belger, C., Neisius, N. M., & Plietker, B. (2010). A Selective Ru-Catalyzed Semireduction of Alkynes to Z Olefins under Transfer-Hydrogenation Conditions. Chemistry - A European Journal, 16(40), 12214-12220. doi:10.1002/chem.201001143 es_ES
dc.description.references Eicher, T., Böhm, S., Ehrhardt, H., Harth, R., & Lerch, D. (1981). Zur Reaktion von Diphenylcyclopropenon, seinen funktionellen Derivaten und Imoniumsalzen mit Aminen. Liebigs Annalen der Chemie, 1981(5), 765-788. doi:10.1002/jlac.198119810503 es_ES
dc.description.references Mazzocchi, P. H., & Thomas, J. J. (1972). Photolysis of N-methyl-2-pyrrolidone. Journal of the American Chemical Society, 94(23), 8281-8282. doi:10.1021/ja00778a085 es_ES
dc.description.references Platz, M. S., & Burns, J. R. (1979). Heteroatomic biradicals. Electron spin resonance spectroscopy of a nitrogen analog of 1,8-naphthoquinodimethane. Journal of the American Chemical Society, 101(15), 4425-4426. doi:10.1021/ja00509a086 es_ES
dc.description.references Leo, E. A., Domingo, L. R., Miranda, M. A., & Tormos, R. (2006). Photogeneration and Reactivity of 1,n-Diphenyl-1,n-azabiradicals. The Journal of Organic Chemistry, 71(12), 4439-4444. doi:10.1021/jo0601967 es_ES
dc.description.references Miranda, M. A., Font-Sanchis, E., Pérez-Prieto, J., & Scaiano, J. C. (1999). Two-Photon Generation of the 1,4-Diphenyl-1,4-butanediyl Biradical:  Direct Detection and Product Studies. The Journal of Organic Chemistry, 64(21), 7842-7845. doi:10.1021/jo990872n es_ES
dc.description.references R. M. Wilson , in Organic Photochemistry , ed. A. Padwa , Marcel Dekker , New York , 1985 , ch. 5, vol. 7 , pp. 339–467 es_ES
dc.description.references Adam, W., Grabowski, S., & Wilson, R. M. (1990). Localized cyclic triplet diradicals. Lifetime determination by trapping with oxygen. Accounts of Chemical Research, 23(5), 165-172. doi:10.1021/ar00173a008 es_ES


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