Lewis Acid Catalyzed [3+2] Coupling of Indoles with Quinone Monoacetals or Quinone Imine Ketal

The one‐pot synthesis of benzofuroindolines and tetrahydroindolo[2,3‐b]indoles was accomplished through a mild and concise [3+2] coupling of indoles and quinone monoacetals or quinone imine ketal promoted by a Lewis acid. A wide variety of benzofuroindolines and tetrahydroindolo[2,3‐b]indoles were p...

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Published inEuropean journal of organic chemistry Vol. 2014; no. 21; pp. 4467 - 4471
Main Authors Shu, Chang, Liao, Li-Hua, Liao, Yi-Jun, Hu, Xiao-Yan, Zhang, Yong-Hong, Yuan, Wei-Cheng, Zhang, Xiao-Mei
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 01.07.2014
WILEY‐VCH Verlag
Wiley
Wiley Subscription Services, Inc
Subjects
Acetals
C-C coupling
Chemistry
Chemistry, Organic
Fused-ring systems
Lewis acids
Nitrogen heterocycles
Physical Sciences
Science & Technology
C-C coupling
CONCISE
DIAZONAMIDE-A
ARYLATION
Lewis acids
ENANTIOSELECTIVE CONSTRUCTION
PYRROLOINDOLINES
TRYPTOPHOLS
Nitrogen heterocycles
ARYL
CYCLOADDITION REACTION
Acetals
CASCADE DEAROMATIZATION
Fused-ring systems
CONJUGATE ADDITION
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Summary:The one‐pot synthesis of benzofuroindolines and tetrahydroindolo[2,3‐b]indoles was accomplished through a mild and concise [3+2] coupling of indoles and quinone monoacetals or quinone imine ketal promoted by a Lewis acid. A wide variety of benzofuroindolines and tetrahydroindolo[2,3‐b]indoles were prepared in moderate to good yields. The [3+2] coupling of indoles and quinone monoacetals or quinone imine ketal promoted by the Lewis acid zinc trifluoromethanesulfonate [Zn(OTf)2] proceeds smoothly to provide various benzofuroindolines and tetrahydroindolo[2,3‐b]indoles in moderate to good yields; Ts = para‐tolylsulfonyl.
Bibliography:istex:143ADA2AF9298EF22F480575D227F650943C1E26
ArticleID:EJOC201402490
ark:/67375/WNG-QBJZPN28-M
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201402490