2024-03-28T06:12:29Zhttps://riubu.ubu.es/oai/requestoai:riubu.ubu.es:10259/67772022-07-21T00:05:22Zcom_10259_3924com_10259_5086com_10259_2604col_10259_3925
2022-07-20T11:04:53Z
urn:hdl:10259/6777
One-Pot Diastereoselective Synthesis of Pyrrolopiperazine-2,6-diones by a Ugi/Nucleophilic Substitution/N-Acylation Sequence
González Saiz, Beatriz
Carreira Barral, Israel
Pertejo Fernández, Pablo
Gómez Ayuso, Javier
Quesada Pato, Roberto
García Valverde, María
Anions
Cesium
Inorganic carbon compounds
Mixtures
Solvents
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).
2022-07-20T11:04:53Z
2022-07-20T11:04:53Z
2022-07
info:eu-repo/semantics/article
0022-3263
http://hdl.handle.net/10259/6777
10.1021/acs.joc.2c00694
1520-6904
eng
The Journal of Organic Chemistry. 2022, V. 87, n. 14, p. 9391–9398
https://doi.org/10.1021/acs.joc.2c00694
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2020-117610RB-I00/ES/SMALL MOLECULE TRANSMEMBRANE ANION CARRIERS FOR BIOLOGICAL APPLICATIONS
info:eu-repo/grantAgreement/Junta de Castilla y León//BU067P20
info:eu-repo/grantAgreement/Junta de Castilla y León//BU075G19
http://creativecommons.org/licenses/by/4.0/
info:eu-repo/semantics/openAccess
Atribución 4.0 Internacional
American Chemical Society