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Synthesis of 2,3-di(ω-hydroxyalkyl)quinolines from anilines and cyclic enols using sequential cycloaddition/aromatization reactions
Tetrahedron Letters ( IF 1.8 ) Pub Date : 2017-11-20 , DOI: 10.1016/j.tetlet.2017.11.034
Carlos Mario Meléndez Gómez , Mario Marsiglia , Ricardo Escarsena , Esther del Olmo , Vladimir V. Kouznetsov

A new synthetic protocol for the one-pot synthesis of 2-(4-hydroxybutyl)-3-(3-hydroxypropyl)quinolines and 3-(2-hydroxyethyl)-2-(3-hydroxypropyl)-quinolines based in the AB2 imino-Diels-Alder reaction is reported. The protocol describes simple and efficient preparation of 2,3-disubstituted quinolines using a domino-sequential process and applying the chemical properties of cyclic enol ethers, such as 2,3-dihydrofuran and 3,4-dihydro-2H-pyran and diverse arylamines, through an imino-Diels-Alder process between an in situ generated 2-azadiene and another equivalent of the cyclic enol, catalyzed by BiCl3, and followed by the aromatization (oxidation) process guided by the MnO2.



中文翻译:

使用顺序环加成/芳构化反应从苯胺和环状烯醇合成2,3-二(ω-羟烷基)喹啉

基于AB 2的一锅式合成2-(4-羟丁基)-3-(3-羟丙基)喹啉和3-(2-羟乙基)-2-(3-羟丙基)喹啉的新合成方案据报道有亚氨基Diels-Alder反应。该协议描述了使用多米诺序列法简单有效地制备2,3-二取代喹啉并应用环状烯醇醚的化学性质,例如2,3-二氢呋喃和3,4-二氢-2 H-吡喃,并且种类繁多芳基胺,通过BiCl 3催化的原位生成的2-氮杂二烯与另一当量的环状烯醇之间的亚氨基Diels-Alder工艺,然后在MnO 2的引导下进行芳构化(氧化)过程。

更新日期:2017-11-20
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