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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Summary: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.
Bibliography:ObjectType-Article-1
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ObjectType-Feature-2
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ISSN:1934-578X
1555-9475
DOI:10.1177/1934578X1100600406