Dearomative [3+2] cycloaddition reaction of nitrobenzothiophenes with nonstabilized azomethine ylides

被引：12
|
作者：
Wang, Kai-Kai [1 ]
Xie, Yan-Xin [2 ]
Li, Yan-Li [3 ]
Chen, Rongxiang [1 ]
Wang, Zhan-Yong [1 ]
机构：
[1] Xinxiang Univ, Sch Pharm, Xinxiang 453000, Henan, Peoples R China
[2] Xinxiang Univ, Sch Chem & Mat Engn, Xinxiang 453000, Henan, Peoples R China
[3] Xinxiang Univ, Med Coll, Xinxiang 453000, Henan, Peoples R China
来源：
RSC ADVANCES | 2020年 / 10卷 / 48期
关键词：
1,3-DIPOLAR CYCLOADDITIONS; FACILE ACCESS; ASYMMETRIC DEAROMATIZATION; ENANTIOSELECTIVE SYNTHESIS; 4+2 ANNULATION; 3-NITROINDOLES; DERIVATIVES; INDOLES; CONSTRUCTION; EFFICIENT;
D O I：
10.1039/d0ra05687a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A highly diastereoselective dearomative [3 + 2] 1,3-dipolar cycloaddition reaction of nitrobenzothiophenes with anin situ-generated nonstabilized azomethine ylides has been developed. The transformation provides a series of functionalized fused tricyclic benzo[4,5]thieno[2,3-c]pyrroles in good yields (up to 92%) under mild reaction conditions. In addition, a gram-scale experiment and the synthetic transformation of the cycloadduct further highlighted the synthetic utility. The relative configurations of the typical products were clearly confirmed by X-ray crystallography.
引用
收藏
页码：28720 / 28724
页数：5
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