Synthesis of pharmacophores containing a prolinate core using a multicomponent 1,3-dipolar cycloaddition of azomethine ylides

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Title: Synthesis of pharmacophores containing a prolinate core using a multicomponent 1,3-dipolar cycloaddition of azomethine ylides
Authors: Selva, Elisabet | Castelló Moncayo, Luis Miguel | Mancebo Aracil, Juan | Selva, Verónica | Nájera, Carmen | Foubelo, Francisco | Sansano, Jose M.
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: Prolinates | Cycloaddition | Azomethine ylides | Multicomponent | Azanucleoside
Knowledge Area: Química Orgánica
Issue Date: 7-Dec-2017
Publisher: Elsevier
Citation: Tetrahedron. 2017, 73(49): 6840-6846. doi:10.1016/j.tet.2017.10.030
Abstract: A multicomponent 1,3-dipolar cycloaddition between heterocyclic aldehydes, amino esters and dipolarophiles is efficiently promoted by silver acetate as catalyst, and depending on the nature of the heterocycle and its reactivity the reaction requires 70 °C or rt to complete. Selected pharmacophores anchored to a formyl group are chromone, 5-methoxyindole, pyridoxal surrogates and a very attractive uracyl derivative. The preference of each tested amino esters towards different dipolarophiles is discussed. At the end, a selective reduction of the ester group allows to obtain a very interesting dideoxiazanucleoside derivative.
Sponsor: We gratefully acknowledge financial support from the Spanish Ministerio de Ciencia e Innovación (MICINN) (projects CTQ2010-20387 and Consolider Ingenio 2010, CSD2007-00006), 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 (projects CTQ2016-76782-P and CTQ2016-81797-REDC), the Generalitat Valenciana (PROMETEO2009/039 and PROMETEOII/2014/017), the University of Alicante and Medalchemy S. L. E. Selva thanks Univerisdad de Alicante and Medalchemy S. L. for a predoctoral fellowship.
URI: http://hdl.handle.net/10045/71257
ISSN: 0040-4020 (Print) | 1464-5416 (Online)
DOI: 10.1016/j.tet.2017.10.030
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.2017.10.030
Appears in Collections:INV - SINTAS - Artículos de Revistas

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