Intramolecular C-sp(2)-C-sp(2) Friedel-Crafts Arylation: Substrate- and Condition-Controlled Divergent Synthesis of Fused-beta-carbolines

A triple cooperative catalysis-mediated multicomponent reaction between 1-formyl-N-substituted-beta-carbolines, a terminal alkyne, and a secondary amine allows access to unprecedented polycyclic beta-carbolines via sequential A(3)-coupling and an intramolecular C-sp(2)-C-sp(2) Friedel Crafts arylati...

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Published inOrganic letters Vol. 18; no. 23; pp. 6010 - 6013
Main Authors Dighe, Shashikant U., Yadav, Veena D., Mahar, Rohit, Shukla, Sanjeev K., Batra, Sanjay
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 02.12.2016
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ANALOGS
STRATEGY
DERIVATIVES
CYCLIZATION
DISCOVERY
ALKALOIDS
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Abstract A triple cooperative catalysis-mediated multicomponent reaction between 1-formyl-N-substituted-beta-carbolines, a terminal alkyne, and a secondary amine allows access to unprecedented polycyclic beta-carbolines via sequential A(3)-coupling and an intramolecular C-sp(2)-C-sp(2) Friedel Crafts arylation reaction. The reaction is successful in a dry inert atmosphere only with substrates bearing a methoxy-substituted benzyl group at the indole nitrogen. Conversely, treating 3-aminoindolizino [8,7-b]indoles (obtained after A(3)-coupling) with acid in the presence of H2O in air offers a general route to natural-alkaloid-like products.
AbstractList A triple cooperative catalysis-mediated multicomponent reaction between 1-formyl-N-substituted-beta-carbolines, a terminal alkyne, and a secondary amine allows access to unprecedented polycyclic beta-carbolines via sequential A(3)-coupling and an intramolecular C-sp(2)-C-sp(2) Friedel Crafts arylation reaction. The reaction is successful in a dry inert atmosphere only with substrates bearing a methoxy-substituted benzyl group at the indole nitrogen. Conversely, treating 3-aminoindolizino [8,7-b]indoles (obtained after A(3)-coupling) with acid in the presence of H2O in air offers a general route to natural-alkaloid-like products.
Author Yadav, Veena D.
Dighe, Shashikant U.
Mahar, Rohit
Batra, Sanjay
Shukla, Sanjeev K.
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Keywords ANALOGS
STRATEGY
DERIVATIVES
CYCLIZATION
DISCOVERY
ALKALOIDS
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Snippet A triple cooperative catalysis-mediated multicomponent reaction between 1-formyl-N-substituted-beta-carbolines, a terminal alkyne, and a secondary amine allows...
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SubjectTerms Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Title Intramolecular C-sp(2)-C-sp(2) Friedel-Crafts Arylation: Substrate- and Condition-Controlled Divergent Synthesis of Fused-beta-carbolines
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