Synthesis of Isoquinolines via the [4+2] Cycloaddition Reaction of Oxazoles and Arynes

被引：4

作者：

Silva, Tamiris R. C. ^{[1
]}

Souza, Vinicius V. ^{[1
]}

Raminelli, Cristiano ^{[1
]}

机构：

[1] Univ Fed Sao Paulo, Inst Ciencias Ambientais Quim & Farmaceut, Rua Prof Artur Riedel 275, BR-09972270 Diadema, SP, Brazil

来源：

CHEMISTRYSELECT | 2022年 / 7卷 / 33期

基金：

巴西圣保罗研究基金会;

关键词：

Benzyne chemistry; Bicyclic ethers; Cycloaddition; Heterocycles; Isoquinolines; POLYSUBSTITUTED PYRIDINES; BENZYNE; GENERATION; PRODUCT; ALKYNES; ISOCYANIDES; ACTIVATION;

D O I：

10.1002/slct.202203039

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein, we report our investigations on the reaction of a variety of substituted oxazoles with o-(trimethylsilyl)aryl triflates promoted by potassium fluoride and 18-crown-6-ether. Several functionalized isoquinoline compounds were obtained in moderate to good yields when the transformation was carried out at room temperature, followed by acidic workup, presumably via a [4+2] cycloaddition-ring-opening reaction pathway. Alternatively, bicyclic ethers were produced in reasonable yields when performing the transformation at 60 degrees C via a sequence of [4+2] cycloaddition, retro-Diels-Alder, and [4+2] cycloaddition reactions.

引用

页数：4

共 66 条

[1]

[Anonymous], 2019, ANGEW CHEM, V131, P2171

[2]

[Anonymous], 2016, ANGEW CHEM, V128, P5667

[3]

Armarego W.L. F., 1996, PURIFICATION LAB CHE, V4th

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