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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Bibliographic Details
Published in:Journal of organic chemistry Vol. 83; no. 24; pp. 15043 - 15056
Main Authors: Selvaraj, Karuppu, Swamy, K. C. Kumara
Format: Journal Article
Language:English
Published: WASHINGTON Amer Chemical Soc 21.12.2018
Subjects:
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
Online Access:Get more information
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Summary: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.
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ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.8b02293