Tetrahedron letters2022，Vol.996.DOI:10.1016/j.tetlet.2022.153797

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

Mamedov, Vakhid A. Galimullina, Venera R. Kadyrova, Saniya F. Rizvanov, Il'dar Kh. Latypov, Shamil K.
Tetrahedron letters2022，Vol.996.DOI:10.1016/j.tetlet.2022.153797
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  • NSTL
  • Elsevier

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

Mamedov, Vakhid A. 1Galimullina, Venera R. 1Kadyrova, Saniya F. 1Rizvanov, Il'dar Kh. 1Latypov, Shamil K.1
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作者信息

  • 1. Russian Acad Sci
  • 折叠

Abstract

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-2carboxamides, proved to be excellent starting compounds for the synthesis 3-chloro(aryl)methyl)-3hydroxyindolin-2-ones with the formation of a new C(sp2)-C(sp2)- bond via intramolecular FriedelCrafts 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. (c) 2022 Published by Elsevier Ltd.

Key words

Synthesis/Friedel-Crafts alkylation/Darzens condensation/Diarylpropanamides/Indol-2-ones/RADICAL CYCLIZATION/ACTIVATED ALKENES/3/3-DISUBSTITUTED OXINDOLES/H FUNCTIONALIZATION/NATURAL-PRODUCTS/CONSTRUCTION/DERIVATIVES/ARYLATION/ARYLACRYLAMIDES/CARBONITRATION

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出版年

2022
Tetrahedron letters

Tetrahedron letters

CCR
ISSN：0040-4039
被引量2
参考文献量69
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