Synthesis of 2-aminobenzofurans via base-mediated [3+2] annulation of N-phenoxy amides with gem-difluoroalkenes

被引：19
|
作者：
Chen, Kaifeng [1 ,2 ,3 ]
Chen, Weijie [1 ,2 ,3 ]
Chen, Fangyuan [1 ,2 ,3 ]
Zhang, Haiman [1 ,2 ,3 ]
Xu, Huiying [1 ,2 ,3 ]
Zhou, Zhi [1 ,2 ,3 ]
Yi, Wei [1 ,2 ,3 ]
机构：
[1] Guangzhou Med Univ, Key Lab Mol Target & Clin Pharmacol, Guangzhou 511436, Guangdong, Peoples R China
[2] Guangzhou Med Univ, State Key Lab Resp Dis, Sch Pharmaceut Sci, Guangzhou 511436, Guangdong, Peoples R China
[3] Guangzhou Med Univ, Affiliated Hosp 5, Guangzhou 511436, Guangdong, Peoples R China
来源：
ORGANIC CHEMISTRY FRONTIERS | 2021年 / 8卷 / 16期
关键词：
C-H FUNCTIONALIZATION; ALPHA-FLUOROALKENYLATION; DIVERSE SYNTHESIS; REARRANGEMENT; BENZOFURANS; ACTIVATION; AMIDATION; LIBRARIES; TANDEM;
D O I：
10.1039/d1qo00709b
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Efficient, mild and metal-free [3 + 2] annulation of N-phenoxy amides with gem-difluoroalkenes has been realized via a base-mediated tandem [3,3]-sigmatropic rearrangement, which gives direct access to 2-aminobenzofuran derivatives involved in the one-pot cleavage of multiple bonds including C-H, O-N and twofold C-F bonds. The subsequent success of the on-DNA compatible synthesis and the application of the obtained products as potential anticancer agents further demonstrates the versatility of this transformation.
引用
收藏
页码：4452 / 4458
页数：7
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