An expeditious FeCl3-catalyzed cascade 1,4-conjugate addition/annulation/1,5-H shift sequence for modular access of all-pyrano-moiety-substituted chromenes

被引：17

作者：

He, Xinwei ^{[1
]}

Li, Ruxue ^{[1
]}

Choy, Pui Ying ^{[2
,3
,4
]}

Duan, Jiahui ^{[1
]}

Yin, Zhenzhen ^{[1
]}

Xu, Keke ^{[1
]}

Tang, Qiang ^{[1
]}

Zhong, Rong-Lin ^{[2
,3
]}

Shang, Yongjia ^{[1
]}

Kwong, Fuk Yee ^{[2
,3
,4
]}

机构：

[1] Anhui Normal Univ, Coll Chem & Mat Sci, Key Lab Funct Mol Solids, Minist Educ, Wuhu 241000, Peoples R China

[2] Chinese Univ Hong Kong, State Key Lab Synthet Chem, Shatin, Hong Kong, Peoples R China

[3] Chinese Univ Hong Kong, Dept Chem, Shatin, Hong Kong, Peoples R China

[4] CUHK Shenzhen Res Inst, Shenzhen Municipal Key Lab Chem Synth Med Organ Mo, Shenzhen Ctr Novel Funct Mol, 10 Second Yuexing Rd, Shenzhen 518507, Peoples R China

来源：

CHEMICAL SCIENCE | 2022年 / 13卷 / 45期

基金：

中国国家自然科学基金;

关键词：

THROUGHPUT SCREENING ASSAY; DISCOVERY; SERIES; 4-ARYL-4H-CHROMENES; HETEROCYCLES; CYCLIZATION; INHIBITORS; ARYLATION; ALKYNES;

D O I：

10.1039/d2sc04431e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

ortho-Alkynyl quinone methides are well-known four-atom synthons for direct [4 + n] cycloaddition in constructing useful oxa-heterocyclic compounds owing to their high reactivity as well as the thermodynamically favored aromatization nature of this process. Herein we report an operationally simple and eco-friendly protocol for the modular and regioselective access of (E)-4-(vinyl or aryl or alkynyl)iminochromenes from propargylamines and S-methylated beta-ketothioamides in the presence of FeCl3, and particularly under undried acetonitrile and air atmosphere conditions. This method exhibits a broad substrate scope and displays nice functional group compatibility, thus providing an efficient access of 3,4-disubstituted iminochromenes.

引用

页码：13617 / 13622

页数：6

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