jo9b02127_si_002.cif (709.23 kB)

BF3·OEt2‑Catalyzed Vinyl Azide Addition to in Situ Generated N‑Acyl Iminium Salts: Synthesis of 3‑Oxoisoindoline-1-acetamides

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posted on 27.11.2019, 13:08 by Deb Kumar Das, Vinod Kumar Kannaujiya, Milon M. Sadhu, Sumit Kumar Ray, Vinod K. Singh
BF3·OEt2-catalyzed nucleophilic addition of vinyl azides to in situ generated N-acyl iminium salts obtained from 3-hydroxyisoindolinones is described in this article. The procedure is operationally simple, mild, additive, and metal-free. The reaction proceeds smoothly at ambient temperature with a wide range of 3-hydroxyisoindol-1-ones and vinyl azides to afford 3-oxoisoindoline-1-acetamides (32 examples) in high yields (up to 97%). Furthermore, the synthetic utility of this methodology is depicted by exploiting the reactivity of an amide functionality in the products.