Phosphine-Catalyzed [3 + 4] Annulations of Salicylaldehyde Schiff Bases with α-Substituted Allenes: Construction of Functionalized Benzoxepine Fused Succinimide Derivatives
{"title":"Phosphine-Catalyzed [3 + 4] Annulations of Salicylaldehyde Schiff Bases with α-Substituted Allenes: Construction of Functionalized Benzoxepine Fused Succinimide Derivatives","authors":"Ke Wu, Xiuqin Ruan, Quanxin Li, Qihe Jiang, Shaofei Ni, Qingfa Zhou","doi":"10.1021/acs.orglett.4c02952","DOIUrl":null,"url":null,"abstract":"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.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9000,"publicationDate":"2024-10-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.4c02952","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
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Abstract
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.
期刊介绍:
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.