RT info:eu-repo/semantics/article
T1 Novel pyrrolobenzodiazepine and pyrroloquinazoline scaffolds synthesized by a simple and highly selective Ugi/cyclization sequence
A1 Pertejo Fernández, Pablo
A1 Peña Calleja, Pablo
A1 Carreira Barral, Israel
A1 Quesada Pato, Roberto
A1 Cordero Tejedor, Nicolás A.
A1 Rodríguez Vidal, Francisco Javier
A1 García Valverde, María
K1 Química orgánica
K1 Chemistry, Organic
AB 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.
PB Royal Society of Chemistry
SN 1477-0520
YR 2017
FD 2017-09
LK http://hdl.handle.net/10259/8088
UL http://hdl.handle.net/10259/8088
LA eng
NO Funding from the Consejería de Educación de la Junta de Castilla y León (projects BU340U13 and BU092U16) is gratefully acknowledged.
DS Repositorio Institucional de la Universidad de Burgos
RD 10-may-2024