2026-06-17T21:52:24Zhttps://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

00925njm 22002777a 4500 dc Pertejo Fernández, Pablo author Peña Calleja, Pablo author Carreira Barral, Israel author Quesada Pato, Roberto author Cordero Tejedor, Nicolás A. author Rodríguez Vidal, Francisco Javier author García Valverde, María author 2017-09 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. 1477-0520 http://hdl.handle.net/10259/8088 10.1039/c7ob01807 1477-0539 Novel pyrrolobenzodiazepine and pyrroloquinazoline scaffolds synthesized by a simple and highly selective Ugi/cyclization sequence