2026-08-22T20:47:42Zhttps://riubu.ubu.es/oai/request

oai:riubu.ubu.es:10259/80882023-11-23T01:05:26Zcom_10259.4_2527com_10259_5086com_10259_2604com_10259_3924col_10259.4_2528col_10259_3925

Pertejo Fernández, Pablo Peña Calleja, Pablo Carreira Barral, Israel Quesada Pato, Roberto Cordero Tejedor, Nicolás A. Rodríguez Vidal, Francisco Javier García Valverde, María 2023-11-22T12:10:48Z 2023-11-22T12:10:48Z 2017-09 1477-0520 http://hdl.handle.net/10259/8088 10.1039/c7ob01807 1477-0539 Pyrrolo[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. Funding from the Consejería de Educación de la Junta de Castilla y León (projects BU340U13 and BU092U16) is gratefully acknowledged. application/pdf eng Royal Society of Chemistry Organic & Biomolecular Chemistry. 2017, V.15, n. 36, p. 7549-7557 https://doi.org/10.1039/C7OB01807J info:eu-repo/grantAgreement/Junta de Castilla y León//BU340U13//IONÓFOROS SINTÉTICOS CON ACTIVIDAD BIOLÓGICA: DISEÑO, SÍNTESIS Y EVALUACIÓN/ info:eu-repo/grantAgreement/Junta de Castilla y León//BU092U16//NUEVOS NANO-TRANSPORTADORES PARA LA ADIMINISTRACION SELECTIVA DE FÁRMACOS ANTITUMORALES/ Química orgánica Chemistry, Organic Novel pyrrolobenzodiazepine and pyrroloquinazoline scaffolds synthesized by a simple and highly selective Ugi/cyclization sequence info:eu-repo/semantics/article info:eu-repo/semantics/acceptedVersion info:eu-repo/semantics/openAccess