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Synthesis of 10-Membered Azecines through Pd-Catalyzed Formal [6+4] Cycloaddition and Their Transannular Reaction to Polycyclic Compounds.
Wang, Yu-Jiao; Zhao, Li-Ming.
Afiliação
  • Wang YJ; School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, 221116, Jiangsu, China.
  • Zhao LM; School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, 221116, Jiangsu, China.
Chemistry ; 29(71): e202302111, 2023 Dec 19.
Article em En | MEDLINE | ID: mdl-37776147
Azecine fragments are frequently presented in natural products and bioactive compounds. However, minor efforts have been devoted to these 10-membered N-heterocycles, and their synthesis is still challenging. Reported herein is the first catalytic formal [6+4] cycloaddition for the synthesis of 10-membered azecines. Under palladium catalysis, the reaction of δ-vinylvalerolactones and benzofuran-derived azadienes proceeds smoothly to afford benzofuran-fused azecines with high diastereoselectivity in moderate to good yields. A unique transannular reaction of these 10-membered azecines for the construction of polycyclic compounds is also demonstrated.
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Texto completo: 1 Base de dados: MEDLINE Idioma: En Ano de publicação: 2023 Tipo de documento: Article

Texto completo: 1 Base de dados: MEDLINE Idioma: En Ano de publicação: 2023 Tipo de documento: Article