Arylative Cyclization of Indole‐1‐carboxamides with 1,6‐Enynes for the Synthesis of Polycyclic Indole Scaffolds

A new alkyne annulation strategy has been developed for the synthesis of polycyclic indole derivatives through a cascade of C–H annulation and Michael addition reactions. This is the first report on sequential alkyne annulation and aza‐Michael addition reactions of indole‐1‐carboxamides with alkyne...

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Published inEuropean journal of organic chemistry Vol. 2017; no. 38; pp. 5763 - 5768
Main Authors Reddy, Chatrala Ravikumar, Yarlagadda, Suresh, Sridhar, Balasubramanian, Reddy, Basi V. Subba
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 17.10.2017
Wiley Subscription Services, Inc
Subjects
Alkynes
Annulation
Cascade chemical reactions
Chemical reactions
Chemistry
Chemistry, Organic
Michael addition
Nitrogen heterocycles
Organic chemistry
Physical Sciences
Polycycles
Scaffolds
Science & Technology
Substrates
Synthesis
Synthetic methods
Transition‐metal catalysis
Michael addition
Transition-metal catalysis
CATALYZED ANNULATION
CASCADE
ALKYNES
C-H ACTIVATION
Polycycles
FUNCTIONALIZATION
Nitrogen heterocycles
Synthetic methods
N BOND FORMATION
Annulation
DERIVATIVES
ACCESS
HYDROARYLATION
ALKALOIDS
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Summary:A new alkyne annulation strategy has been developed for the synthesis of polycyclic indole derivatives through a cascade of C–H annulation and Michael addition reactions. This is the first report on sequential alkyne annulation and aza‐Michael addition reactions of indole‐1‐carboxamides with alkyne tethered substrates. A facile synthesis of polycyclic indole derivatives is reported through a sequential C–C and C–N bond formation using transition metal catalysis.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201701029