Synthesis of Pyrrolidinoindolines from 2-(2-Oxo-3-indolyl)acetates: Scope and Limitations

A series of 1,3a,8-alkylpyrrolidinoindolines have been synthesized. The scope and limitations of the alkylation of starting methyl oxindol-3-acetates are explored employing electron-rich and electron-poor alkylating agents. Hydrolysis and reductive lactonization of the resulting carboxylic γ-oxindol...

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Published inNatural product communications Vol. 6; no. 4; pp. 457 - 464
Main Authors Morales-Ríos, Martha S., Rivera-Becerril, Ernesto, González-Juárez, Daphne E., García-Vázquez, Juan Benjamín, Trujillo-Serrato, Joel J., Hernández-Barragán, Angelina, Joseph-Nathan, Pedro
Format Journal Article
LanguageEnglish
Published Los Angeles, CA SAGE Publications 01.04.2011
Subjects
Acetates - chemistry
Indoles - chemistry
Pyrrolidines - chemical synthesis
2-oxofuroindolines
Pyrrolidinoindolines
3,3-dialkyloxindoles
electron-rich and electron poor alkylating agents
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Abstract A series of 1,3a,8-alkylpyrrolidinoindolines have been synthesized. The scope and limitations of the alkylation of starting methyl oxindol-3-acetates are explored employing electron-rich and electron-poor alkylating agents. Hydrolysis and reductive lactonization of the resulting carboxylic γ-oxindolic acid derivatives proceeds with good yields to afford 2-oxofuroindolines providing ready access to the pyrrolidinoindoline derivatives.
AbstractList A series of 1,3a,8-alkylpyrrolidinoindolines have been synthesized. The scope and limitations of the alkylation of starting methyl oxindol-3-acetates are explored employing electron-rich and electron-poor alkylating agents. Hydrolysis and reductive lactonization of the resulting carboxylic γ-oxindolic acid derivatives proceeds with good yields to afford 2-oxofuroindolines providing ready access to the pyrrolidinoindoline derivatives.
A series of 1,3a,8-alkylpyrrolidinoindolines have been synthesized. The scope and limitations of the alkylation of starting methyl oxindol-3-acetates are explored employing electron-rich and electron-poor alkylating agents. Hydrolysis and reductive lactonization of the resulting carboxylic gamma-oxindolic acid derivatives proceeds with good yields to afford 2-oxofuroindolines providing ready access to the pyrrolidinoindoline derivatives.
Author Rivera-Becerril, Ernesto
Morales-Ríos, Martha S.
González-Juárez, Daphne E.
Trujillo-Serrato, Joel J.
Hernández-Barragán, Angelina
Joseph-Nathan, Pedro
García-Vázquez, Juan Benjamín
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10.1021/jm800277g
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10.1021/jo0012647
10.1177/1934578X0800300421
10.1128/AEM.69.6.3469-3475.2003
10.3987/COM-06-10759
10.1021/jo981577q
10.1016/j.phytochem.2007.04.030
10.2174/0929867033457511
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Keywords 2-oxofuroindolines
Pyrrolidinoindolines
3,3-dialkyloxindoles
electron-rich and electron poor alkylating agents
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Morales-Ríos, Suárez-Castillo, Trujillo-Serrato, Joseph-Nathan 2001; 66
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Morales-Ríos, Suárez-Castillo 2008; 3
Kai, Horita, Wakasa, Miyagawa 2007; 68
Peters, Koning, Wright, Pukall, Stackebrandt, Eberl, Riedel 2003; 69
Miyamoto, Okawa, Nakasaki, Kobayashi 2007; 48
Suárez-Castillo, Meléndez-Rodríguez, Castelán-Duarte, Sánchez-Zavala, Rivera-Becerril, Morales-Ríos, Joseph-Nathan 2009; 20
Morales-Ríos, Rivera-Becerril, Joseph-Nathan 2005; 16
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Snippet A series of 1,3a,8-alkylpyrrolidinoindolines have been synthesized. The scope and limitations of the alkylation of starting methyl oxindol-3-acetates are...
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SubjectTerms Acetates - chemistry
Indoles - chemistry
Pyrrolidines - chemical synthesis
Title Synthesis of Pyrrolidinoindolines from 2-(2-Oxo-3-indolyl)acetates: Scope and Limitations
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