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Palladium-Catalysed C−H/N−H Annulations of (E,Z)-3-Arylidene Indolin-2-ones with Alkynes: A Synthesis of Benzazepine Derivatives

We developed an efficient palladium-catalyzed synthesis of benzazepine derivatives from ( E,Z )-3-(arylidene)indolin-2-ones with alkynes, affording the desired products in good yields. The reaction proceeds via a palladium-catalyzed C−H/N−H activation,… Click to show full abstract

We developed an efficient palladium-catalyzed synthesis of benzazepine derivatives from ( E,Z )-3-(arylidene)indolin-2-ones with alkynes, affording the desired products in good yields. The reaction proceeds via a palladium-catalyzed C−H/N−H activation, followed by alkyne insertion and reductive elimination sequences. Furthermore, we have also demonstrated the gram scale reaction as well as some synthetic transformations of the annulated products.

Keywords: arylidene indolin; synthesis benzazepine; ones alkynes; benzazepine derivatives; indolin ones

Journal Title: Synlett
Year Published: 2025

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