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

共 50 条

[11] Trivalent Phosphine-Catalyzed [4+1] Spiro-annulation Reaction Using Allenyl Imide and Methylene Cyclocompounds
Zhang, Zi-Qiu
Zhang, Zhen-Kai
Wang, Yu-Hao
Chen, Bo-Ting
He, Feng-Kai
Wang, Yi-Long
Shu, Tao
Huang, Yi-Yong
JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (09): : 6607 - 6614
[12] Pd-Catalyzed [4+1] Annulation Strategy to Functionalized 4-Methyleneproline Derivatives
Han, Jiaxin
Gao, Wenzheng
Harrity, Joseph P. A.
JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (03): : 1552 - 1555
[13] An expedient phosphine-catalyzed [4+2] annulation: Synthesis of highly functionalized tetrahydropyridines
Zhu, XF
Lan, J
Kwon, O
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (16) : 4716 - 4717
[14] Phosphine-Initiated Cascade Annulation of β′-Acetoxy Allenoate and p-Quinols: Access to Ring Fused Hexahydroindeno Furan Derivatives
Xing, Jiao-Jiao
Gao, Yu-Ning
Shi, Min
ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (13) : 2552 - 2559
[15] Phosphine-Catalyzed (4+1) Annulation: Rearrangement of Allenylic Carbamates to 3-Pyrrolines through Phosphonium Diene Intermediates
Blank, Brian R.
Andrews, Ian P.
Kwon, Ohyun
CHEMCATCHEM, 2020, 12 (17) : 4352 - 4372
[16] An Unexpected Phosphine-Catalyzed Regio- and Diastereoselective [4+1] Annulation Reaction of Modified Allylic Compounds with Activated Enones
Chen, Zuliang
Zhang, Junliang
CHEMISTRY-AN ASIAN JOURNAL, 2010, 5 (07) : 1542 - 1545
[17] Facile access to highly functionalized hydroisoquinoline derivatives via phosphine-catalyzed sequential [3+3]/[3+3] annulation
Li, Ning
Jia, Penghao
Huang, You
CHEMICAL COMMUNICATIONS, 2019, 55 (73) : 10976 - 10979
[18] Phosphine-Catalyzed [4+3] Annulation for the Synthesis of Highly Functionalized Bicyclo[3.2.2]nonadienes
Zheng, Suqing
Lu, Xiyan
ORGANIC LETTERS, 2009, 11 (17) : 3978 - 3981
[19] Phosphine-catalyzed [4+1] annulation of 1,3-(aza)dienes with maleimides: highly efficient construction of azaspiro[4.4]nonenes
Yang, Mei
Wang, Tianyi
Cao, Shixuan
He, Zhengjie
CHEMICAL COMMUNICATIONS, 2014, 50 (88) : 13506 - 13509
[20] Phosphine-catalyzed [4+1] annulation of 2-tosylaminochalcones with allenoates: synthesis of trans-2,3-disubstitued indolines
Gao, Zhenzhen
Wang, Chang
Yuan, Chunhao
Zhou, Leijie
Xiao, Yumei
Guo, Hongchao
CHEMICAL COMMUNICATIONS, 2015, 51 (63) : 12653 - 12656

← 1 2 3 4 5 →