Synthesis of 3,3-Disubstituted 2-Oxindoles by Deacylative Alkylation of 3-Acetyl-2-oxindoles

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Title: Synthesis of 3,3-Disubstituted 2-Oxindoles by Deacylative Alkylation of 3-Acetyl-2-oxindoles
Authors: Ortega-Martínez, Aitor | Molina, Cynthia | Moreno-Cabrerizo, Cristina | Sansano, Jose M. | Nájera, Carmen
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 | Michael addition | Triton­ B
Knowledge Area: Química Orgánica
Issue Date: 22-Aug-2017
Publisher: Georg Thieme Verlag
Citation: Synthesis. 2017, 49(23): 5203-5210. doi:10.1055/s-0036-1590880
Abstract: An innovative and efficient monoalkylation and nonsymmetrical 3,3-dialkylation of oxindoles has been achieved. First, the monoalkylation of 3-acetyl-2-oxindoles can be performed in good yields under mild reaction conditions using alkyl halides and benzyltrimethylammonium hydroxide (Triton B) as base at room temperature. This methodology is applied to construct the synthetically challenging compound 1,3-dimethyl-2-oxindole. Subsequent deacylative alkylation (DaA) of the alkylated 3-acetyl-2-oxindoles with alkyl halides takes place efficiently using LiOEt or by conjugate addition with electron-deficient alkenes in the presence of Triton B at room temperature under argon, affording the corresponding unsymmetrically 3,3-disubstituted 2-oxindoles. This simple methodology has been applied to the synthesis of precursors of horsfiline, esermethole, physostigmine, and phenserine alkaloids.
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 (FEDER, EU) (projects CTQ2016-76782-P and CTQ2016-81797-REDC), the Generalitat Valenciana (PROMETEO2009/039 and PROMETEOII/ 2014/017) and the University of Alicante. A.O.-M. thanks MINECO for a predoctoral fellowship.
URI: http://hdl.handle.net/10045/71354
ISSN: 0039-7881 (Print) | 1437-210X (Online)
DOI: 10.1055/s-0036-1590880
Language: eng
Type: info:eu-repo/semantics/article
Rights: © Georg Thieme Verlag Stuttgart · New York
Peer Review: si
Publisher version: http://dx.doi.org/10.1055/s-0036-1590880
Appears in Collections:INV - SINTAS - Artículos de Revistas

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