2026-05-07T12:58:05Zhttps://riubu.ubu.es/oai/request

oai:riubu.ubu.es:10259/67772022-07-21T00:05:22Zcom_10259_3924com_10259_5086com_10259_2604col_10259_3925

González Saiz, Beatriz Carreira Barral, Israel Pertejo Fernández, Pablo Gómez Ayuso, Javier Quesada Pato, Roberto García Valverde, María 2022-07-20T11:04:53Z 2022-07-20T11:04:53Z 2022-07 0022-3263 http://hdl.handle.net/10259/6777 10.1021/acs.joc.2c00694 1520-6904 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). 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. application/pdf eng American Chemical Society 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 Atribución 4.0 Internacional http://creativecommons.org/licenses/by/4.0/ info:eu-repo/semantics/openAccess Anions Cesium Inorganic carbon compounds Mixtures Solvents Química orgánica Chemistry, Organic One-Pot Diastereoselective Synthesis of Pyrrolopiperazine-2,6-diones by a Ugi/Nucleophilic Substitution/N-Acylation Sequence info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion The Journal of Organic Chemistry 87 14 9391 9398