Superacid-catalyzed tandem Meyer-Schuster rearrangement/intramolecular hydroamination of o-anilinopropargyl alcohols for the synthesis of 2,3-dihydro-4(1H)-quinolones

被引：9

作者：

Sun, Guofeng ^{[1
]}

Cheng, Fengkai ^{[1
]}

Tao, Ruiheng ^{[1
]}

Sun, Yuxing ^{[1
]}

Pan, Jinpeng ^{[1
]}

Zhu, Yaohua ^{[1
]}

Wang, Zhonghua ^{[1
]}

Wu, Fanhong ^{[1
]}

Yin, Yan ^{[1
,2
]}

机构：

[1] Shanghai Inst Technol, Sch Chem & Environm Engn, 100 Hai Quan Rd, Shanghai 201418, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai, Peoples R China

来源：

SYNTHETIC COMMUNICATIONS | 2016年 / 46卷 / 15期

基金：

中国国家自然科学基金;

关键词：

2; 3-Dihydro-4(1H)-quinolones; hydroamination reaction; Meyer-Schuster rearrangement; o-anilinopropargyl alcohols; superacid; INTRAMOLECULAR HYDROAMINATION; TETRAHYDROQUINOLINES; REARRANGEMENT; SULFONAMIDES; DERIVATIVES; CYCLIZATION; SERIES;

D O I：

10.1080/00397911.2016.1196293

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A TfOH-catalyzed synthesis of 2,3-dihydro-4(1H)-quinolones from o-anilinopropargyl alcohols was developed. Studies of N-protecting groups and substituents in phenyl rings showed that diverse groups could be applied. By controlling the catalyst loading, o-anilinopropargyl alcohols underwent the expected transformation smoothly to produce N-protected or N-deprotected 2,3-dihydro-4 (1H)-quinolones in good yields. This transformation probably involved a tandem Meyer-Schuster rearrangement/intramolecular hydroamination reaction process. [GRAPHICS] .

引用

页码：1249 / 1256

页数：8

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