This research demonstrates a novel method to synthesize C(2)-alkylated pseudoindoxyls using vinyl azides, indicating new pathways for functionalization.
Herein, a divergent coupling of indole-derived C,N-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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BARUAH et al. (2026) studied this question.
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