Domino alkyne insertion/aldol reaction/aromatization of 2-alkynyl indole-3-carbaldehyde with 1,3-diketones: entry to 2-indolyl phenols

A novel one-pot base-promoted insertion of indolyl 2-alkynes into a C-C single bond of 1,3-diketones, followed by intramolecular aldol reaction and dehydrative aromatization is described. This reaction cascade leads to the construction of 2-indolyl phenols involving the formation of the C1-C2 and C3...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2023-02, Vol.21 (5), p.146-155
Main Authors: Raji Reddy, Chada, Nair, Karna, Patil, Amol D, Donthiri, Ramachandra Reddy, Grée, René
Format: Article
Language:English
Subjects:
Aldehydes
Alkynes
Chemical reactions
Chemical Sciences
Dehydration
Diketones
Insertion
Organic chemistry
Phenols
Reagents
Substrates
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Summary:A novel one-pot base-promoted insertion of indolyl 2-alkynes into a C-C single bond of 1,3-diketones, followed by intramolecular aldol reaction and dehydrative aromatization is described. This reaction cascade leads to the construction of 2-indolyl phenols involving the formation of the C1-C2 and C3-C4 bonds of phenols resulting from the formal insertion process with a good substrate scope. Further, these bifunctional compounds were used in a novel arylative annulation in the presence of Grignard reagents to provide chromeno-indole frameworks. Base mediated metal-free construction of 2-indolyl phenols was developed from 2-alkynyl indole-3-carbaldehyde. The obtained products led to a unique strategy to access dihydrochromeno[4,3- b ]indoles.
ISSN:1477-0520
1477-0539
DOI:10.1039/d2ob02025d