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dc.contributor.authorPertejo Fernández, Pablo
dc.contributor.authorPeña Calleja, Pablo 
dc.contributor.authorCarreira Barral, Israel 
dc.contributor.authorQuesada Pato, Roberto 
dc.contributor.authorCordero Tejedor, Nicolás A. 
dc.contributor.authorRodríguez Vidal, Francisco Javier 
dc.contributor.authorGarcía Valverde, María 
dc.date.accessioned2023-11-22T12:10:48Z
dc.date.available2023-11-22T12:10:48Z
dc.date.issued2017-09
dc.identifier.issn1477-0520
dc.identifier.urihttp://hdl.handle.net/10259/8088
dc.description.abstractPyrrolo[2,1-c][1,4]benzodiazepines (PBDs) and other benzo-fused N-heterocycles constitute privileged structures found in numerous bioactive compounds. Thus, developing simple and selective syntheses to furnish these derivatives from easily accessible starting materials is an important and challenging goal. In this work, novel pyrrolobenzodiazepine and pyrroloquinazoline derivatives have been synthesized following a common two step synthetic strategy. This strategy involves a one-pot Ugi/cyclization sequence followed by a reduction with spontaneous thermocontrolled cyclization. The control of the temperature in this second step allows fully selective access to either pyrrolo[2,1-c][1,4]benzodiazepine-3-ones 6 or pyrrolo[2,1-b]quinazolines 7. Density functional theory (DFT) calculations have been carried out to rationalize this reactivity, identifying the kinetic and thermodynamic reaction products and offering insights into the cyclization pathways. These synthetic methodologies show the versatility of the Ugi reaction as a tool in the synthesis of heterocyclic compounds with a pseudopeptidic skeleton.en
dc.description.sponsorshipFunding from the Consejería de Educación de la Junta de Castilla y León (projects BU340U13 and BU092U16) is gratefully acknowledged.en
dc.format.mimetypeapplication/pdf
dc.language.isoenges
dc.publisherRoyal Society of Chemistryen
dc.relation.ispartofOrganic & Biomolecular Chemistry. 2017, V.15, n. 36, p. 7549-7557en
dc.subject.otherQuímica orgánicaes
dc.subject.otherChemistry, Organicen
dc.titleNovel pyrrolobenzodiazepine and pyrroloquinazoline scaffolds synthesized by a simple and highly selective Ugi/cyclization sequenceen
dc.typeinfo:eu-repo/semantics/articlees
dc.rights.accessRightsinfo:eu-repo/semantics/openAccesses
dc.relation.publisherversionhttps://doi.org/10.1039/C7OB01807Jes
dc.identifier.doi10.1039/c7ob01807
dc.relation.projectIDinfo:eu-repo/grantAgreement/Junta de Castilla y León//BU340U13//IONÓFOROS SINTÉTICOS CON ACTIVIDAD BIOLÓGICA: DISEÑO, SÍNTESIS Y EVALUACIÓN/es
dc.relation.projectIDinfo:eu-repo/grantAgreement/Junta de Castilla y León//BU092U16//NUEVOS NANO-TRANSPORTADORES PARA LA ADIMINISTRACION SELECTIVA DE FÁRMACOS ANTITUMORALES/es
dc.identifier.essn1477-0539
dc.type.hasVersioninfo:eu-repo/semantics/acceptedVersiones


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