Ultrasound-mediated radical cascade reactions: Fast synthesis of functionalized indolines from 2-(((N-aryl)amino)methyl)acrylates
| Autor: | Vinicius R. Nascimento, Leandro H. Andrade, Julia L. Couto, Milene M. Hornink, Caroline S. Santos |
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| Rok vydání: | 2021 |
| Předmět: |
Acoustics and Ultrasonics
Sonication Sono-Fenton QC221-246 Organic synthesis Review Article Catalysis Inorganic Chemistry chemistry.chemical_compound SÍNTESE ORGÂNICA Ultrasound Chemical Engineering (miscellaneous) Environmental Chemistry Radiology Nuclear Medicine and imaging QD1-999 ComputingMethodologies_COMPUTERGRAPHICS Aryl Organic Chemistry Acoustics. Sound Combinatorial chemistry Chemistry Ultrasonic horn Indolines chemistry Pulsed ultrasound Indoline Anhydrous Formamides Functionalized indolines |
| Zdroj: | Ultrasonics Sonochemistry Repositório Institucional da USP (Biblioteca Digital da Produção Intelectual) Universidade de São Paulo (USP) instacron:USP Ultrasonics Sonochemistry, Vol 79, Iss, Pp 105778-(2021) |
| ISSN: | 1873-2828 |
| Popis: | Graphical abstract Highlights • The use of the sono-Fenton process for molecular construction is described for the first time. • Ultrasound-mediated radical cascade reactions enable the fast synthesis of indolines in high yields (up to 99%). • A straightforward and easy-to-implement methodology for the synthesis of indolines was developed. • An ultrasonic horn, an open reaction flask, and a green catalyst are our key tools. 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 %). |
| Databáze: | OpenAIRE |
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