Deacylative alkylation (DaA) of N-methyl-3-acetyl-2-oxindole for the synthesis of symmetrically 3,3-disubstituted 2-oxindoles. An access gate to anticancer agents and natural products

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Title: Deacylative alkylation (DaA) of N-methyl-3-acetyl-2-oxindole for the synthesis of symmetrically 3,3-disubstituted 2-oxindoles. An access gate to anticancer agents and natural products
Authors: Moreno-Cabrerizo, Cristina | Ortega-Martínez, Aitor | Molina, Cynthia | Nájera, Carmen | 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: Deacylation | Alkylation | 2-oxindoles | Metathesis | Anticancer | Natural products
Knowledge Area: Química Orgánica
Issue Date: 2018
Publisher: Academia Brasileira de Ciências
Citation: Anais da Academia Brasileira de Ciências. 2018, 90(1 Suppl. 2): 1089-1099. doi:10.1590/0001-3765201820170783
Abstract: The synthesis of 3,3-disubstituted N-methyloxindoles, starting from 3-acetyl-2-hydroxy-1-methyloxindole employing a sequential one-pot synthesis, is studied. The process involves a first alkylation in the presence of 1 equiv. of both organic halide and Triton B and the second one employs another 1.5 equiv. of each in moderate to high yields. This procedure is compared with the results obtained from the direct dialkylation of N-methyloxindole. The metathesis of one of the corresponding diallylated product was also studied obtaining the spiranic oxindole. All these methodologies are directed towards the access to anticancer agents and natural biologically active products.
Sponsor: Financial support was provided by 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), by the Generalitat Valenciana (PROMETEO2009/039 and PROMETEOII/ 2014/017) and by the University of Alicante. Aitor Ortega-Martínez thanks MINECO for a predoctoral fellowship.
URI: http://hdl.handle.net/10045/76371
ISSN: 0001-3765 | 1678-2690 (Online)
DOI: 10.1590/0001-3765201820170783
Language: eng
Type: info:eu-repo/semantics/article
Rights: Creative Commons Attribution License
Peer Review: si
Publisher version: https://doi.org/10.1590/0001-3765201820170783
Appears in Collections:INV - SINTAS - Artículos de Revistas

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