Synthesis of highly functionalized 2-(pyrrolidin-1-yl)thiazole frameworks with interesting antibacterial and antimycobacterial activity

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Title: Synthesis of highly functionalized 2-(pyrrolidin-1-yl)thiazole frameworks with interesting antibacterial and antimycobacterial activity
Authors: Belveren, Samet | Dondas, H. Ali | Ülger, Mahmut | Poyraz, Samet | García-Mingüens, Eduardo | Ferrándiz-Saperas, Marcos | Sansano, Jose M.
Research Group/s: Síntesis Asimétrica (SINTAS)
Center, Department or Service: Universidad de Alicante. Departamento de Química Orgánica
Keywords: Prolinates | Thiazole | Antibacterial | Antimycobacterial
Knowledge Area: Química Orgánica
Issue Date: 30-Nov-2017
Publisher: Elsevier
Citation: Tetrahedron. 2017, 73(48): 6718-6727. doi:10.1016/j.tet.2017.10.007
Abstract: A versatile, facile and concise approach to access to highly substituted functionalized 2-(pyrrolidin-1-yl)thiazole ring system is accomplished. The efficient protocol proceeds by the reaction of corresponding racemic or enantiomerically enriched pyrrolidines and readily available benzoylisothiocyanate in acetonitrile followed by sequential reaction of readily available alpha-bromo ketones in acetone. The selectivity and good yield in the desired product is another important advantage of this reaction protocol. In a few cases, the resulting N-benzoylthiourea intermediate cyclizes spontaneously before reacting with the benzophenone component. Finally, a wide study of the biological scope of this new bisheterocyclic molecules is reported.
Sponsor: This work is a part of Samet Belveren's ongoing PhD thesis granted by Mersin University (Project no. BAP-SBE TEB(SB) 2017-2-TP3-2564). The authors thank Mersin University (Turkey) and the University of Alicante for support. We also thank the Scientific and Technological Research Council of Turkey (TÜBİTAK), 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), (Consolider Ingenio 2010, CSD2007-00006) for research financing.
URI: http://hdl.handle.net/10045/70888
ISSN: 0040-4020 (Print) | 1464-5416 (Online)
DOI: 10.1016/j.tet.2017.10.007
Language: eng
Type: info:eu-repo/semantics/article
Rights: © 2017 Elsevier Ltd.
Peer Review: si
Publisher version: http://dx.doi.org/10.1016/j.tet.2017.10.007
Appears in Collections:INV - SINTAS - Artículos de Revistas

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