Phosphine-Catalyzed 3 + 4 Annulations of Salicylaldehyde Schiff Bases with α-Substituted Allenes: Construction of Functionalized Benzoxepine Fused Succinimide Derivatives

• Published in: Organic letters 2024-11, Vol.26 (44), p.9425
• Main Authors: Wu, Ke, Ruan, Xiuqin, Li, Quanxin, Jiang, Qihe, Ni, Shaofei, Zhou, Qingfa
• Format: Article
• Language: English
• ISSN: 1523-7052; 1523-7052
• DOI: 10.1021/acs.orglett.4c02952

Herein we reported a novel strategy for constructing benzoxepine fused succinimide derivatives via a phosphine-catalyzed [3 + 4] cyclization of α-substituted allenes and salicylaldehyde Schiff bases. This methodology serves as a conduit for the construction of benzoxepine derivatives in good yields under mild conditions by an unprecedented mode involving the β'-carbon of allenes. Density functional theory calculations were conducted to study the possible mechanism. Moreover, this class of compounds exhibited the potential ability of cytotoxicity toward cancer cells.Herein we reported a novel strategy for constructing benzoxepine fused succinimide derivatives via a phosphine-catalyzed [3 + 4] cyclization of α-substituted allenes and salicylaldehyde Schiff bases. This methodology serves as a conduit for the construction of benzoxepine derivatives in good yields under mild conditions by an unprecedented mode involving the β'-carbon of allenes. Density functional theory calculations were conducted to study the possible mechanism. Moreover, this class of compounds exhibited the potential ability of cytotoxicity toward cancer cells.