From Bioactive Pyrrolidino[3,4-c]pyrrolidines to more Bioactive Pyrrolidino[3,4-b]pyrrolidines via Ring-Opening/Ring-Closing Promoted by Sodium Methoxide

Please use this identifier to cite or link to this item: http://hdl.handle.net/10045/89887
Información del item - Informació de l'item - Item information
Title: From Bioactive Pyrrolidino[3,4-c]pyrrolidines to more Bioactive Pyrrolidino[3,4-b]pyrrolidines via Ring-Opening/Ring-Closing Promoted by Sodium Methoxide
Authors: Belveren, Samet | Larrañaga Agirre, Olatz | Poyraz, Samet | Dondas, H. Ali | Ülger, Mahmut | Şahin, Ertan | Ferrándiz-Saperas, Marcos | Sansano, Jose M. | Retamosa Hernández, María de Gracia | Cózar Ruano, Abel de
Research Group/s: Síntesis Asimétrica (SINTAS)
Center, Department or Service: Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica
Keywords: Cycloaddition | Azomethine ylides | Rearrangement | Antibacterials | DFT calculations
Knowledge Area: Química Orgánica
Issue Date: 2019
Publisher: Georg Thieme Verlag
Citation: Synthesis. 2019, 51(07): 1565-1577. doi:10.1055/s-0037-1611356
Abstract: The process involving a rearrangement of pyrrolidino[3,4-c]pyrrolidine to another pyrrolidino[3,4-b]pyrrolidine using sodium methoxide as base is fully studied. The effects of the substituents are analyzed during the ring-opening/ring-closing sequence. Computational studies are also performed to explain the importance of susbstituents and quaternary carbons, especially when the (3-indolyl)methyl is present in the starting material. Finally, all the samples are evaluated as potential candidates for antibacterial and antimycobacterial activities.
Sponsor: We are grateful for support from Mersin University [Project no: MEU-2017-COL-01007-M150D and BAP-SBE AKB (SB) 2012-8 YL and BAP 2015- AP2-1342]. We gratefully acknowledge financial support from the Spanish Ministerio de Economía y Competitividad (MINECO) (projects CTQ2013-43446-P and CTQ2014-51912-REDC), the Spanish Ministerio de Economía, Industria y Competitividad, Agencia Estatal de Investigación (AEI) and Fondo Europeo de Desarrollo Regional (FEDER, EU) (projects CTQ2016-76782-P and CTQ2016-81797-REDC), the Generalitat Valenciana (PROMETEOII/2014/017), the Gobierno Vasco/Eusko Jaurlaritza (GV/EJ, grant IT673-13), and the University of Alicante. O.L. gratefully acknowledges UPV/EHU for her postdoctoral grant. O.L. and A.d.C. gratefully thank SGI/IZO-SGIker and DIPC for generous allocation of computational resources.
URI: http://hdl.handle.net/10045/89887
ISSN: 0039-7881 (Print) | 1437-210X (Online)
DOI: 10.1055/s-0037-1611356
Language: eng
Type: info:eu-repo/semantics/article
Rights: © Georg Thieme Verlag Stuttgart · New York
Peer Review: si
Publisher version: https://doi.org/10.1055/s-0037-1611356
Appears in Collections:INV - SINTAS - Artículos de Revistas

Files in This Item:
Files in This Item:
File Description SizeFormat 
Thumbnail2019_Belveren_etal_Synthesis_final.pdfVersión final (acceso restringido)2,16 MBAdobe PDFOpen    Request a copy
Thumbnail2019_Belveren_etal_Synthesis_accepted.pdfEmbargo 12 meses (acceso abierto: 13 dic. 2019)1,51 MBAdobe PDFOpen    Request a copy


Items in RUA are protected by copyright, with all rights reserved, unless otherwise indicated.