Ultrasound-mediated radical cascade reactions: Fast synthesis of functionalized indolines from 2-(((N-aryl)amino)methyl)acrylates
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, includi...
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| Format: | Article |
| Language: | English |
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Elsevier
2021-11-01
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| Series: | Ultrasonics Sonochemistry |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S1350417721003205 |
| _version_ | 1818925361212162048 |
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| author | Milene M. Hornink Vinicius R. Nascimento Julia L. Couto Caroline S. Santos Leandro H. Andrade |
| author_facet | Milene M. Hornink Vinicius R. Nascimento Julia L. Couto Caroline S. Santos Leandro H. Andrade |
| author_sort | Milene M. Hornink |
| collection | DOAJ |
| description | 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 %). |
| first_indexed | 2024-12-20T02:40:00Z |
| format | Article |
| id | doaj.art-0a4a267930184fde8ca4d443d73a4310 |
| institution | Directory Open Access Journal |
| issn | 1350-4177 |
| language | English |
| last_indexed | 2024-12-20T02:40:00Z |
| publishDate | 2021-11-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Ultrasonics Sonochemistry |
| spelling | doaj.art-0a4a267930184fde8ca4d443d73a43102022-12-21T19:56:20ZengElsevierUltrasonics Sonochemistry1350-41772021-11-0179105778Ultrasound-mediated radical cascade reactions: Fast synthesis of functionalized indolines from 2-(((N-aryl)amino)methyl)acrylatesMilene M. Hornink0Vinicius R. Nascimento1Julia L. Couto2Caroline S. Santos3Leandro H. Andrade4Instituto de Química, Universidade de São Paulo, Av. Prof. Lineu Prestes, 748, CEP 05508-000 São Paulo, SP, BrazilInstituto de Química, Universidade de São Paulo, Av. Prof. Lineu Prestes, 748, CEP 05508-000 São Paulo, SP, BrazilInstituto de Química, Universidade de São Paulo, Av. Prof. Lineu Prestes, 748, CEP 05508-000 São Paulo, SP, BrazilInstituto de Química, Universidade de São Paulo, Av. Prof. Lineu Prestes, 748, CEP 05508-000 São Paulo, SP, BrazilCorresponding author.; Instituto de Química, Universidade de São Paulo, Av. Prof. Lineu Prestes, 748, CEP 05508-000 São Paulo, SP, BrazilNovel 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 %).http://www.sciencedirect.com/science/article/pii/S1350417721003205IndolinesSono-FentonUltrasoundPulsed ultrasoundFunctionalized indolinesOrganic synthesis |
| spellingShingle | Milene M. Hornink Vinicius R. Nascimento Julia L. Couto Caroline S. Santos Leandro H. Andrade Ultrasound-mediated radical cascade reactions: Fast synthesis of functionalized indolines from 2-(((N-aryl)amino)methyl)acrylates Ultrasonics Sonochemistry Indolines Sono-Fenton Ultrasound Pulsed ultrasound Functionalized indolines Organic synthesis |
| title | Ultrasound-mediated radical cascade reactions: Fast synthesis of functionalized indolines from 2-(((N-aryl)amino)methyl)acrylates |
| title_full | Ultrasound-mediated radical cascade reactions: Fast synthesis of functionalized indolines from 2-(((N-aryl)amino)methyl)acrylates |
| title_fullStr | Ultrasound-mediated radical cascade reactions: Fast synthesis of functionalized indolines from 2-(((N-aryl)amino)methyl)acrylates |
| title_full_unstemmed | Ultrasound-mediated radical cascade reactions: Fast synthesis of functionalized indolines from 2-(((N-aryl)amino)methyl)acrylates |
| title_short | Ultrasound-mediated radical cascade reactions: Fast synthesis of functionalized indolines from 2-(((N-aryl)amino)methyl)acrylates |
| title_sort | ultrasound mediated radical cascade reactions fast synthesis of functionalized indolines from 2 n aryl amino methyl acrylates |
| topic | Indolines Sono-Fenton Ultrasound Pulsed ultrasound Functionalized indolines Organic synthesis |
| url | http://www.sciencedirect.com/science/article/pii/S1350417721003205 |
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