Phosphine-Catalyzed [4+1] Annulation of β'-Acetoxy Allenoate with α-Alkylidene Succinimides: Access to Functionalized Spirosuccinimide Derivatives

被引：0

作者：

Ni, Chunjie ^{[1
]}

Liang, Zhanhang ^{[1
,3
]}

Xu, Xiaojuan ^{[1
,3
]}

Yu, Fan ^{[1
]}

Zhao, Yining ^{[1
]}

Chen, Chen ^{[2
]}

机构：

[1] Yancheng Teachers Univ, Sch Pharm, Yancheng 224007, Peoples R China

[2] Tianjin Normal Univ, Coll Chem, Tianjin 300387, Peoples R China

[3] Nanjing Tech Univ, Coll Biotechnol & Pharmaceut Engn, Nanjing 211816, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 22期

基金：

中国国家自然科学基金;

关键词：

3+2 CYCLOADDITION; ASYMMETRIC-SYNTHESIS; 2,3-BUTADIENOATES; 2-BUTYNOATES; ITACONIMIDES; FACILE; YLIDES;

D O I：

10.1021/acs.joc.4c02014

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A phosphine-catalyzed [4 + 1] annulation of beta'-acetoxy allenoate with alpha-alkylidene succinimides is described. This method demonstrates the nucleophilic dialkylation and cyclization of alpha-alkylidene succinimides, resulting in the formation of functionalized spirosuccinimide derivatives. The reaction exhibits a wide substrate scope and yields ranging from moderate to excellent under the optimized conditions. In addition, the biological evaluation indicates that the cycloadduct 3u presents satisfied inhibitory activities for three human cancer cell lines (HCT116, A549, and HepG2).

引用

页码：16711 / 16720

页数：10

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