Transition-Metal-Free, Bronsted Acid-Mediated Cascade Sequence in the Reaction of Propargyl Alcohols with Sulfonamido-indoles/- indolines: Highly Substituted delta- and alpha-Carbolines

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

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Vydáno v:Journal of organic chemistry Ročník 83; číslo 24; s. 15043 - 15056
Hlavní autoři: Selvaraj, Karuppu, Swamy, K. C. Kumara
Médium: Journal Article
Jazyk:angličtina
Vydáno: WASHINGTON Amer Chemical Soc 21.12.2018
Témata:
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
MIGRATION
ANALOGS
CATALYZED SYNTHESIS
REGIOSELECTIVE SYNTHESIS
C-C
SELECTIVE SYNTHESIS
TANDEM REACTION
DERIVATIVES
ACCESS
BETA
ISSN:0022-3263, 1520-6904, 1520-6904
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Shrnutí:Bronsted acid-mediated, transition-metal-free reaction of propargyl alcohols with sulfonamido-indoles/indolines under mild conditions affords highly substituted delta- or alpha-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 alpha-carbolines has also been discovered.
Bibliografie:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.8b02293