Application of Pyridinium 1,4-Zwitterionic Thiolates: Synthesis of Benzopyridothiazepines and Benzothiophenes

被引：41

作者：

Cheng, Bin ^{[1
,2
]}

Li, Yuntong ^{[2
]}

Wang, Taimin ^{[1
]}

Zhang, Xinping ^{[2
]}

Li, Hui ^{[2
]}

He, Yixuan ^{[2
]}

Li, Yun ^{[2
]}

Zhai, Hongbin ^{[1
,2
,3
]}

机构：

[1] Shenzhen Polytech, Inst Marine Biomed, Shenzhen 518055, Peoples R China

[2] Lanzhou Univ, State Key Lab Appl Organ Chem, Coll Chem & Chem Engn, Lanzhou 730000, Peoples R China

[3] Peking Univ, State Key Lab Chem Oncogen, Shenzhen Engn Lab Nano Drug Slow Release, Shenzhen Grad Sch, Shenzhen 518055, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 10期

关键词：

CATALYZED SYNTHESIS; ARYNES; DERIVATIVES; CYCLOADDITION; SULFUR; ANNULATION; TRIFLATE; CASCADE; ARYL;

D O I：

10.1021/acs.joc.0c00374

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Pyridinium 1,4-zwitterionic thiolates, as a novel kind of sulfur-containing synthon, have been applied to the synthesis of 12aH-benzo[f]pyrido [1,2-d] [1,4]thiazepines and benzo[b]thiophenes. Benzopyridothiazepines were produced through a 1,5-dipolar cycloaddition reaction from pyridinium 1,4-zwitterionic thiolates with arynes, whereas benzothiophenes as side products were generated via a [3 + 2] cascade cyclization reaction. The [5 + 2] reaction mode of pyridinium 1,4-zwitterionic thiolates is disclosed for the first time.

引用

页码：6794 / 6802

页数：9

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