Transition-Metal-Free, Brønsted Acid-Mediated Cascade Sequence in the Reaction of Propargyl Alcohols with Sulfonamido-indoles/-indolines: Highly Substituted δ- and α‑Carbolines

Brønsted acid-mediated, transition-metal-free reaction of propargyl alcohols with sulfonamido-indoles/-indolines under mild conditions affords highly substituted δ- or α-carbolines in good to excellent yields. This protocol involves cascade reaction sequences of Friedel–Crafts alkylation/ [1,5]-hydr...

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Published inJournal of organic chemistry Vol. 83; no. 24; pp. 15043 - 15056
Main Authors Selvaraj, Karuppu, Swamy, K. C. Kumara
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.12.2018
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
MIGRATION
ANALOGS
CATALYZED SYNTHESIS
REGIOSELECTIVE SYNTHESIS
C-C
SELECTIVE SYNTHESIS
TANDEM REACTION
DERIVATIVES
ACCESS
BETA
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Summary:Brønsted acid-mediated, transition-metal-free reaction of propargyl alcohols with sulfonamido-indoles/-indolines under mild conditions affords highly substituted δ- or α-carbolines in good to excellent yields. This protocol involves cascade reaction sequences of Friedel–Crafts alkylation/ [1,5]-hydrogen shift/electrocyclization/elimination/ [1,2]-aryl migration followed by aromatization. An unexpected regioselective tosyl group migration from indole 2- to 6-position and arene elimination leading to α-carbolines has also been discovered.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b02293