Domino alkyne insertion/aldol reaction/aromatization of 2-alkynyl indole-3-carbaldehyde with 1,3-diketones: entry to 2-indolyl phenols - Université de Rennes Accéder directement au contenu
Article Dans Une Revue Organic & Biomolecular Chemistry Année : 2023

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

Résumé

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.
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hal-03969066 , version 1 (14-03-2023)

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Paternité - Pas d'utilisation commerciale

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Chada Raji Reddy, Karna Nair, Amol D. Patil, Ramachandra Reddy Donthiri, René Grée. Domino alkyne insertion/aldol reaction/aromatization of 2-alkynyl indole-3-carbaldehyde with 1,3-diketones: entry to 2-indolyl phenols. Organic & Biomolecular Chemistry, 2023, 21, pp.1046-1055. ⟨10.1039/d2ob02025d⟩. ⟨hal-03969066⟩
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