A concise synthesis of indolin-2-ones via direct acid-catalyzed intramolecular Friedel-Crafts alkylation of 3-chloro-N-(substituted)-2-oxo-N,3-diarylpropanamides

[Display omitted] 3-Chloro-2-oxo-N,3-diarylpropanamides, readily obtained from aromatic aldehydes and dichloroacetic acid anilides under Darzens condensation conditions or isomerization of 2-chloro-N,3-diaryloxirane-2-carboxamides, proved to be excellent starting compounds for the synthesis 3-chloro...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron letters 2022-06, Vol.99, p.153797, Article 153797
Main Authors: Mamedov, Vakhid A., Galimullina, Venera R., Kadyrova, Saniya F., Rizvanov, Il′dar Kh, Latypov, Shamil K.
Format: Article
Language:English
Subjects:
Darzens condensation
Diarylpropanamides
Friedel-Crafts alkylation
Indol-2-ones
Synthesis
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:[Display omitted] 3-Chloro-2-oxo-N,3-diarylpropanamides, readily obtained from aromatic aldehydes and dichloroacetic acid anilides under Darzens condensation conditions or isomerization of 2-chloro-N,3-diaryloxirane-2-carboxamides, proved to be excellent starting compounds for the synthesis 3-chloro(aryl)methyl)-3-hydroxyindolin-2-ones with the formation of a new C(sp2)–C(sp2)- bond via intramolecular Friedel-Crafts alkylation. Under optimized reaction conditions, the title compounds are obtained in a one-pot process, which involves a treatment of N-benzyl-3-chloro-2-oxo-N,3-diarylpropanamides with a CF3CO2H. The reactions proceed with the formation of easily separated by column chromatography anti and syn diastereomeric mixtures with a predominance of 36–49% of the formers.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2022.153797