Three-Component Domino Reactions for Selective Formation of Indeno[1,2‑b]indole Derivatives

Efficient three-component domino strategies for the synthesis of multifunctionalized tetracyclic indeno[1,2-b]indole derivatives with different substituted patterns have been established successfully. The first pathway involves a novel sequential methyl migration, aromatization, and esterification,...

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Bibliographic Details
Published inOrganic letters Vol. 14; no. 20; pp. 5210 - 5213
Main Authors Jiang, Bo, Li, Qiu-Yun, Tu, Shu-Jiang, Li, Guigen
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.10.2012
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Indoles - chemical synthesis
Models, Molecular
Molecular Structure
Physical Sciences
Science & Technology
Stereoisomerism
GENERATION
INDOLE
HETEROCYCLES
CYCLIZATION REACTIONS
DNA
NINHYDRIN
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Summary:Efficient three-component domino strategies for the synthesis of multifunctionalized tetracyclic indeno[1,2-b]indole derivatives with different substituted patterns have been established successfully. The first pathway involves a novel sequential methyl migration, aromatization, and esterification, while a second reaction in HOAc leads to compounds 6 with high syn diastereoselectivity. Both reactions showed attractive features including mild conditions, convenient one-pot operation, short reaction times of 15–32 min, and excellent regio- and/or stereoselectivity.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol3023038