Ultrasound-mediated radical cascade reactions: Fast synthesis of functionalized indolines from 2-(((N-aryl)amino)methyl)acrylates.

Autor: Hornink MM; Instituto de Química, Universidade de São Paulo, Av. Prof. Lineu Prestes, 748, CEP 05508-000 São Paulo, SP, Brazil., Nascimento VR; Instituto de Química, Universidade de São Paulo, Av. Prof. Lineu Prestes, 748, CEP 05508-000 São Paulo, SP, Brazil., Couto JL; Instituto de Química, Universidade de São Paulo, Av. Prof. Lineu Prestes, 748, CEP 05508-000 São Paulo, SP, Brazil., Santos CS; Instituto de Química, Universidade de São Paulo, Av. Prof. Lineu Prestes, 748, CEP 05508-000 São Paulo, SP, Brazil., Andrade LH; Instituto de Química, Universidade de São Paulo, Av. Prof. Lineu Prestes, 748, CEP 05508-000 São Paulo, SP, Brazil. Electronic address: leandroh@iq.usp.br.
Jazyk: angličtina
Zdroj: Ultrasonics sonochemistry [Ultrason Sonochem] 2021 Nov; Vol. 79, pp. 105778. Date of Electronic Publication: 2021 Oct 07.
DOI: 10.1016/j.ultsonch.2021.105778
Abstrakt: 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%; FeSO 4 ·7H 2 O; 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 %).
(Copyright © 2021 The Author(s). Published by Elsevier B.V. All rights reserved.)
Databáze: MEDLINE
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