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Ultrasound-mediated radical cascade reactions: Fast synthesis of functionalized indolines from 2-(((N-aryl)amino)methyl)acrylates
Ultrasonics Sonochemistry ( IF 8.4 ) Pub Date : 2021-10-07 , DOI: 10.1016/j.ultsonch.2021.105778
Milene M Hornink 1 , Vinicius R Nascimento 1 , Julia L Couto 1 , Caroline S Santos 1 , Leandro H Andrade 1
Affiliation  

Novel functionalized indolines were synthesized from 2-(((N-aryl)amino)methyl)acrylates and formamides under ultrasonic irradiation for the first time. Aiming to develop a straightforward and easy-to-implement methodology for the synthesis of indolines, an instrumentation setup was designed, including ultrasound (US) equipment (Ultrasonic Horn; tip diameter of 12.7 mm, 20 kHz, maximum power of 400 W), an open reaction flask, and an inexpensive and green catalyst (1 mol%; FeSO4·7H2O; CAS: 7782–63–0) without the need for anhydrous conditions. The use of the sono-Fenton process in the presence of formamides and 2-(((N-aryl)amino)methyl)acrylates afforded a broad range of functionalized indolines within 60 s in high yields. Several experimental parameters of the ultrasound-assisted reaction were evaluated, such as amplitude (40–80%), sonication time (15–60 s), and pulsed ultrasonic irradiation. A 60 s silent reaction did not produce the desired indoline. The optimized conditions for US-mediated reactions allowed the production of functionalized indolines in high isolated yields (up to 99%, 60 s reaction, pulse ration 1 s:1 s, US amplitude 60 %).



中文翻译:

超声介导的自由基级联反应:从 2-(((N-芳基)氨基)甲基)丙烯酸酯快速合成功能化二氢吲哚

首次在超声辐照下由 2-((( N-芳基)氨基)甲基)丙烯酸酯和甲酰胺合成了新型功能化二氢吲哚。为了开发一种简单且易于实施的二氢吲哚合成方法,设计了一种仪器设置,包括超声(美国)设备(超声波喇叭;尖端直径为 12.7 毫米,20 kHz,最大功率为 400 W),一个开放式反应烧瓶,以及一种廉价且绿色的催化剂(1 mol%;FeSO 4 ·7H 2 O;CAS:7782-63-0),无需无水条件。在甲酰胺和 2-((( N-芳基)氨基)甲基)丙烯酸酯在 60 秒内以高产率提供了广泛的官能化二氢吲哚。评估了超声辅助反应的几个实验参数,例如振幅(40-80%)、超声处理时间(15-60 秒)和脉冲超声辐照。60 秒的静默反应没有产生所需的二氢吲哚。US 介导反应的优化条件允许以高分离产率生产官能化二氢吲哚(高达 99%,60 秒反应,脉冲比 1 秒:1 秒,US 振幅 60%)。

更新日期:2021-10-12
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