An Efficient Multi‐Component Double Friedel‐Crafts Alkylation of Isatin: Access to Unsymmetrical and Symmetrical 3, 3‐Diaryl oxindoles

Abstract Acetic acid‐mediated three‐component double Friedel–Crafts alkylation reaction for the synthesis of α, α‐diaryl oxindole derivatives is demonstrated. The reaction is successful with various isatin, indole, and N, N ‐disubstituted aniline derivatives. The efficiency of the reaction is further enhanced by a four‐component reaction of isatin, electrophiles and acetic anhydride for the synthesis of N ‐acylated 3,3‐diaryl oxindole derivatives facilitated by dual activation of C3 and N 1 acetylation in a single‐step. Various unsymmetrical and symmetrical 3,3‐diaryl oxindoles were prepared in single‐step MCR reaction under easy to operate reaction conditions.

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Journal
ChemistrySelect
Published
2024-09-30
DOI
https://doi.org/10.1002/slct.202403328
Citations
1
Primary Topic
Chemical Synthesis and Reactions
Type
article
Field-Weighted Citation Impact
0.25
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article

An Efficient Multi‐Component Double Friedel‐Crafts Alkylation of Isatin: Access to Unsymmetrical and Symmetrical 3, 3‐Diaryl oxindoles

Navyasree Pilli, Malapaka Chandrasekharam, Sudheer Kumar Karu
1 citations
ChemistrySelect
Chemical Synthesis and Reactions
0.25
article

An Efficient Multi‐Component Double Friedel‐Crafts Alkylation of Isatin: Access to Unsymmetrical and Symmetrical 3, 3‐Diaryl oxindoles

Navyasree Pilli, Malapaka Chandrasekharam, Sudheer Kumar Karu
article en
1 citations

Abstract

Abstract Acetic acid‐mediated three‐component double Friedel–Crafts alkylation reaction for the synthesis of α, α‐diaryl oxindole derivatives is demonstrated. The reaction is successful with various isatin, indole, and N, N ‐disubstituted aniline derivatives. The efficiency of the reaction is further enhanced by a four‐component reaction of isatin, electrophiles and acetic anhydride for the synthesis of N ‐acylated 3,3‐diaryl oxindole derivatives facilitated by dual activation of C3 and N 1 acetylation in a single‐step. Various unsymmetrical and symmetrical 3,3‐diaryl oxindoles were prepared in single‐step MCR reaction under easy to operate reaction conditions.

ChemistrySelectVol. 9(37)
Indian Institute of Chemical Technology (IN), Academy of Scientific and Innovative Research (IN)
Openalex Percentile: Top 48%
Chemical Synthesis and Reactions
0.25
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