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Lewis Acid-Catalyzed Switchable Functionalization of C,N-Cyclic Ketimines with Vinyl Azides: Access to Diverse C(2)-Alkylated Pseudoindoxyls.

PubMed
Authors: Baruah A, Baruah M, Bulbul RM, Dey SK, More AA

Year

2026

Paper ID

68609

Status

Peer-reviewed

Abstract Read

~2 min

Abstract Words

67

Citations

0

Abstract

Herein, a divergent coupling of indole-derived ,-cyclic ketimines with vinyl azides is described for the synthesis of structurally diverse C(2)-alkylated pseudoindoxyls, especially α-indoxylacetamides, ketones, and acetonitrile derivatives. The Lewis acid-catalyzed divergent Schmidt and interrupted Schmidt-type pathways of the transient iminodiazonium ion intermediate enable vinyl azides to effectively function as surrogates for amides, ketones, and cyanomethanides. Furthermore, α-indoxylacetamides exhibited fluorescence properties, demonstrating an impressive fluorescence quantum yield.

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  • Herein, a divergent coupling of indole-derived ,-cyclic ketimines with vinyl azides is described for the synthesis of structurally diverse C(2)-alkylated pseudoindoxyls...

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References & Citation Signals

[1] DOI https://doi.org/10.1021/acs.joc.5c03190 [2] Publisher https://pubmed.ncbi.nlm.nih.gov/41855212/

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