2026-05-07T08:15:58Zhttps://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 b9e6524a-c9e8-44a9-9cf8-befd2d6cd56a 600 Peña Calleja, Pablo 426 600 0000-0001-9483-9808 Carreira Barral, Israel 763 600 0000-0002-4835-8752 Quesada Pato, Roberto 458 600 0000-0003-2764-7157 Cordero Tejedor, Nicolás A. 128 600 0000-0002-3609-4163 Rodríguez Vidal, Francisco Javier 482 600 0000-0001-8866-4757 García Valverde, María 222 600 0000-0002-3990-8388 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 THUMBNAIL Pertejo-obc_2017.pdf.jpg Pertejo-obc_2017.pdf.jpg IM Thumbnail image/jpeg 4823 https://riubu.ubu.es/bitstream/10259/8088/3/Pertejo-obc_2017.pdf.jpg c90123e27e90367c26cd43755494ff9b MD5 3 LICENSE license.txt license.txt text/plain; charset=utf-8 999 https://riubu.ubu.es/bitstream/10259/8088/2/license.txt b295bcbce42e2caabeb0c623d3860c06 MD5 2 ORIGINAL Pertejo-obc_2017.pdf Pertejo-obc_2017.pdf application/pdf 873667 https://riubu.ubu.es/bitstream/10259/8088/1/Pertejo-obc_2017.pdf 79a64b5efa98b387d9f8addc585e4a14 MD5 1 10259/8088 oai:riubu.ubu.es:10259/8088 2023-11-23 02:05:26.492 Repositorio Institucional de la Universidad de Burgos bubrep@ubu.es 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