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Palladium-Catalyzed Cascade 5-endo-dig Cyclization of Ynamides to Form 4-Alkynyloxazolones.
Goulart, Tales A C; Back, Davi Fernando; Moura E Silva, Sidnei; Zeni, Gilson.
Afiliación
  • Goulart TAC; Laboratório de Síntese, Reatividade, Avaliação Farmacológica e Toxicológica de Organocalcogênios CCNE, UFSM, Santa Maria, Rio Grande do Sul 97105-900, Brazil.
  • Back DF; Laboratório de Materiais Inorgânicos, Departamento de Química, UFSM, Santa Maria, Rio Grande do Sul 97105-900, Brazil.
  • Moura E Silva S; Laboratório de Biotecnologia de Produtos Naturais e Sintéticos, Instituto de Biotecnologia, Universidade de Caxias do Sul, Caxias do Sul, Rio Grande do Sul 95070-560, Brazil.
  • Zeni G; Laboratório de Síntese, Reatividade, Avaliação Farmacológica e Toxicológica de Organocalcogênios CCNE, UFSM, Santa Maria, Rio Grande do Sul 97105-900, Brazil.
J Org Chem ; 87(5): 3341-3351, 2022 03 04.
Article en En | MEDLINE | ID: mdl-35167299
The selective synthesis of 4-alkynyloxazolones and their further applications as substrates to electrophile-promoted nucleophilic cyclization have been developed. The reaction of ynamides with terminal alkynes proceeded smoothly to give 4-alkynyloxazolones in the presence of a catalytic amount of palladium(II) acetate. The products were obtained with the sequential formation of new C-C and C-O bonds via a cascade procedure. The first step involved a carbon-oxygen bond formation, via a 5-endo-dig closure, which was confirmed by X-ray analyses of the crystalline sample. Subsequently, the reaction of 4-alkynyloxazolones with an electrophilic selenium source gave 3-phenylselanyl benzofuran derivatives via an electrophile-promoted nucleophilic cyclization.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Paladio Idioma: En Revista: J Org Chem Año: 2022 Tipo del documento: Article País de afiliación: Brasil Pais de publicación: Estados Unidos
Texto completo
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XML
PubMed Links
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Paladio Idioma: En Revista: J Org Chem Año: 2022 Tipo del documento: Article País de afiliación: Brasil Pais de publicación: Estados Unidos