(3+1) Annulation/Rearrangement Cascade of C,N-Cyclic Azomethine Imines and 3-Chlorooxindoles: Construction of Hexahydroindeno[2,1-c]pyrazole Spirooxindole Frameworks

被引：16
|
作者：
Zheng, Peng-Fei [1 ]
Zeng, Rong [1 ]
Jiang, Kun [1 ]
Li, Hong-Wei [1 ]
Ye, Ying [1 ]
Mu, Chao [2 ]
Shuai, Li [1 ]
Quyang, Qin [1 ]
Chen, Ying-Chun [1 ,3 ,4 ]
机构：
[1] Third Mil Med Univ, Coll Pharm, Chongqing 400038, Peoples R China
[2] Sichuan Univ Sci & Engn, Coll Chem & Environm Engn, Zigong 643000, Peoples R China
[3] Sichuan Univ, West China Sch Pharm, Key Lab Drug Targeting & Drug Delivery Syst, Minist Educ, Chengdu 610041, Sichuan, Peoples R China
[4] Sichuan Univ, West China Sch Pharm, Sichuan Res Ctr Drug Precis Ind Technol, Chengdu 610041, Sichuan, Peoples R China
来源：
ORGANIC LETTERS | 2019年 / 21卷 / 24期
基金：
国家重点研发计划;
关键词：
ENANTIOSELECTIVE 1,3-DIPOLAR CYCLOADDITION; 4+1 ANNULATION; ASYMMETRIC-SYNTHESIS; AMMONIUM YLIDES; ACCESS; ALLENOATES;
D O I：
10.1021/acs.orglett.9b03996
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The Bronsted base promoted (3 + 1) annulation reaction of C,N-cyclic azomethine imines and 3-chlorooxindoles was investigated, finally delivering complex hexahydroindeno[2,1-c] pyrazoles incorporating a spirocyclic oxindole motif after an unexpected rearrangement process. The asymmetric version of this new transformation could be accomplished, but slow racemization of the chiral product was observed at ambient temperature. Experiments and DFT calculations were further conducted to elucidate the reaction process and racemization mechanism.
引用
收藏
页码：10052 / 10056
页数：5
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