2026-04-22T22:03:02Zhttps://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 d85c2f90-326d-457f-954a-54c0194d36a2 600 Carreira Barral, Israel 703d8822-8907-4c5b-9bdd-773fda8112db 600 Pertejo Fernández, Pablo b9e6524a-c9e8-44a9-9cf8-befd2d6cd56a 600 Gómez Ayuso, Javier c1a51865-cdde-4202-a435-1c5c9fa53cab Quesada Pato, Roberto 458 600 García Valverde, María 222 600 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 THUMBNAIL Gonzalez-joc_2022.pdf.jpg Gonzalez-joc_2022.pdf.jpg IM Thumbnail image/jpeg 5164 https://riubu.ubu.es/bitstream/10259/6777/5/Gonzalez-joc_2022.pdf.jpg 7da9242677cc33901ba5bd9b678b3fcd MD5 5 Gonzalez-joc_2022-Supporting-infomation.pdf.jpg Gonzalez-joc_2022-Supporting-infomation.pdf.jpg IM Thumbnail image/jpeg 3553 https://riubu.ubu.es/bitstream/10259/6777/6/Gonzalez-joc_2022-Supporting-infomation.pdf.jpg bab4ffa08ad4628d0166234f12f5c303 MD5 6 LICENSE license.txt license.txt text/plain; charset=utf-8 999 https://riubu.ubu.es/bitstream/10259/6777/4/license.txt b295bcbce42e2caabeb0c623d3860c06 MD5 4 CC-LICENSE license_rdf license_rdf application/rdf+xml; charset=utf-8 908 https://riubu.ubu.es/bitstream/10259/6777/3/license_rdf 0175ea4a2d4caec4bbcc37e300941108 MD5 3 ORIGINAL Gonzalez-joc_2022.pdf Gonzalez-joc_2022.pdf application/pdf 1678652 https://riubu.ubu.es/bitstream/10259/6777/1/Gonzalez-joc_2022.pdf 890d973cf94661feaf4b90f2ae452923 MD5 1 Gonzalez-joc_2022-Supporting-infomation.pdf Gonzalez-joc_2022-Supporting-infomation.pdf application/pdf 5700339 https://riubu.ubu.es/bitstream/10259/6777/2/Gonzalez-joc_2022-Supporting-infomation.pdf da497c24de4f960925b3257202f3f265 MD5 2 10259/6777 oai:riubu.ubu.es:10259/6777 2022-07-21 02:05:22.891 Repositorio Institucional de la Universidad de Burgos bubrep@ubu.es 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