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

共 50 条

[1] CONVENIENT SYNTHESIS OF 2,3-DIHYDRO-4(1H)-QUINOLONES
MERCHANT, JR
CHOTHIA, DS
INDIAN JOURNAL OF CHEMISTRY, 1972, 10 (02): : 243 - &
[2] CHROMANONES, THIOCHROMANONES AND 2,3-DIHYDRO-4(1H)-QUINOLONES
HURD, CD
HAYAO, S
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (20) : 5065 - 5069
[3] SYNTHESIS OF QUINOLINES AND 2,3-DIHYDRO-4(1H)-QUINOLONES - PALLADIUM CATALYZED REACTION OF O-IODOANILIDES WITH ACETYLENIC CARBINOLS
KUNDU, NG
MAHANTY, JS
DAS, P
DAS, B
TETRAHEDRON LETTERS, 1993, 34 (10) : 1625 - 1628
[4] Synthesis of 2,3-dihydro-4(1H)-quinazolinones
Escalante, J
Flores, P
Priego, JM
HETEROCYCLES, 2004, 63 (09) : 2019 - 2032
[5] Fe(OTf)3-catalyzed tandem Meyer-Schuster rearrangement/intermolecular hydroamination of 3-aryl propargyl alcohols for the synthesis of acyclic β-Aminoketones
Tao, Ruiheng
Yin, Yan
Duan, Yongbin
Sun, Yuxing
Sun, Yue
Cheng, Fengkai
Pan, Jinpeng
Lu, Cheng
Wang, Yuan
TETRAHEDRON, 2017, 73 (13) : 1762 - 1768
[6] Synthesis of 2,3-Dihydro-4(1H)-quinolones and the Corresponding 4(1H)-Quinolones via Low-Temperature Fries Rearrangement of N-Arylazetidin-2-ones
Lange, Jens
Bissember, Alex C.
Banwell, Martin G.
Cade, Ian A.
AUSTRALIAN JOURNAL OF CHEMISTRY, 2011, 64 (04) : 454 - 470
[7] Palladium-catalyzed heteroannulation with acetylenic carbinols as synthons - Synthesis of quinolines and 2,3-dihydro-4(1H)-quinolones
Mahanty, JS
De, M
Das, P
Kundu, NG
TETRAHEDRON, 1997, 53 (39) : 13397 - 13418
[8] Synthesis of 2,3-dihydro-4(1H)-quinolinone derivatives
Mickevichius, VJ
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1996, (04): : 523 - 526
[9] Synthesis of 2,3-Dihydro-4(1H)-quinoline Derivatives
Chemistry of Heterocyclic Compounds, 1996, 32 (04)
[10] SYNTHESES IN ISOQUINOLINE SERIES . SYNTHESIS OF 2,3-DIHYDRO-4(1H)-ISOQUINOLONES
GRETHE, G
LEE, HL
USKOKOVI.M
BROSSI, A
JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (02): : 491 - &

← 1 2 3 4 5 →