Lewis Acid-Catalyzed [4+2] Annulation between Propargylic Alcohols with Benzo[d]isoxazoles

被引：29

作者：

Han, Ya-Ping ^{[1
]}

Li, Xue-Song ^{[1
]}

Sun, Zhou ^{[1
]}

Zhu, Xin-Yu ^{[1
]}

Li, Ming ^{[1
]}

Song, Xian-Rong ^{[2
]}

Liang, Yong-Min ^{[1
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China

[2] Jiangxi Sci Technol Normal Univ, Jiangxi Key Lab Organ Chem, Nanchang 330013, Jiangxi, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2017年 / 359卷 / 16期

基金：

美国国家科学基金会;

关键词：

benzo[d]isoxazoles; 4+2] cascade annulation; Lewis acid catalysis; propargylic alcohols; quinoline derivatives; MEYER-SCHUSTER REARRANGEMENT; DONOR-ACCEPTOR CYCLOPROPANES; 3+2 CROSS-CYCLOADDITION; TANDEM REACTION; REGIOSELECTIVE SYNTHESIS; ACRIDONE ALKALOIDS; FACILE SYNTHESIS; DERIVATIVES; CYCLIZATION; DIVERGENT;

D O I：

10.1002/adsc.201700495

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An unprecedented copper(II) trifluoromethanesulfonate-catalyzed [4+2] cascade annulation of propargylic alcohols with benzo[d] isoxazoles proceeds through a sequential ring opening/Meyer-Schuster rearrangement/intermolecular cyclization. This protocol, which tolerates a broad variety of functional groups, offers a versatile, modular and atom-economical access to a new class of fascinating quinoline derivatives in good yields under mild conditions. The transformation could be scaled up to a gram scale efficiently, thus highlighting the synthetic utility of this methodology.

引用

页码：2735 / 2740

页数：6

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