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BF3·OEt2-Catalyzed Vinyl Azide Addition to in Situ Generated N-Acyl Iminium Salts: Synthesis of 3-Oxoisoindoline-1-acetamides.
Kumar Das, Deb; Kannaujiya, Vinod Kumar; Sadhu, Milon M; Ray, Sumit Kumar; Singh, Vinod K.
Afiliación
  • Kumar Das D; Department of Chemistry , Indian Institute of Science Education and Research Bhopal , Bhopal , MP 462066 , India.
  • Kannaujiya VK; Department of Chemistry , Indian Institute of Science Education and Research Bhopal , Bhopal , MP 462066 , India.
  • Sadhu MM; Department of Chemistry , Indian Institute of Science Education and Research Bhopal , Bhopal , MP 462066 , India.
  • Ray SK; Department of Chemistry , Indian Institute of Science Education and Research Bhopal , Bhopal , MP 462066 , India.
  • Singh VK; Department of Chemistry , Indian Institute of Technology Kanpur , Kanpur , UP 208016 , India.
J Org Chem ; 84(24): 15865-15876, 2019 Dec 20.
Article en En | MEDLINE | ID: mdl-31741383
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.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: J Org Chem Año: 2019 Tipo del documento: Article País de afiliación: India Pais de publicación: Estados Unidos
Texto completo
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: J Org Chem Año: 2019 Tipo del documento: Article País de afiliación: India Pais de publicación: Estados Unidos