RT info:eu-repo/semantics/article
T1 One-Pot Diastereoselective Synthesis of Pyrrolopiperazine-2,6-diones by a Ugi/Nucleophilic Substitution/N-Acylation Sequence
A1 González Saiz, Beatriz
A1 Carreira Barral, Israel
A1 Pertejo Fernández, Pablo
A1 Gómez Ayuso, Javier
A1 Quesada Pato, Roberto
A1 García Valverde, María
K1 Anions
K1 Cesium
K1 Inorganic carbon compounds
K1 Mixtures
K1 Solvents
K1 Química orgánica
K1 Chemistry, Organic
AB The diastereoselective synthesis of two families of pyrrolopiperazine-2,6-diones is presented. These compounds were prepared by one-pot Ugi/nucleophilic substitution/N-acylation/debenzoylation/(elimination) sequences. This novel route provides straightforward access to a wide variety of pyrrolopiperazine-2,6-diones with high chemical yields and complete diastereoselectivities. The proposed synthetic strategy poses a significant improvement compared to the syntheses of pyrrolopiperazine-2,6-diones previously described, as it allows introduction of different substituents to the C4 position and the diastereoselective generation of a new stereogenic center on the bridgehead carbon (C8a).
PB American Chemical Society
SN 0022-3263
YR 2022
FD 2022-07
LK http://hdl.handle.net/10259/6777
UL http://hdl.handle.net/10259/6777
LA eng
NO Funding from Consejería de Educación de la Junta de Castilla y León and FEDER (project BU075G19 and project BU067P20) and MCIN/AEI/10.13039/501100011033 (grant PID2020-117610RB-I00) is gratefully acknowledged. B.G.-S. and J.G.-A. thank Consejería de Educación de la Junta de Castilla y León for their predoctoral contracts. We also thank Inés María del Olmo for her contributions to the synthesis of some of the reported compounds.
DS Repositorio Institucional de la Universidad de Burgos
RD 01-may-2024