Visible light-induced green synthesis of 2-amino-4H-chromenes
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ORIGINAL PAPER
Visible light‑induced green synthesis of 2‑amino‑4H‑chromenes Lu Chen1 · Chuyuan Lin1 · Yongyin Lan1 · Zhenzhen Li1 · Dandan Huang1 · Wei Yang2 · Yibiao Li1 Received: 10 May 2020 / Accepted: 11 July 2020 © Springer Nature Switzerland AG 2020
Abstract Green chemistry aims at developing reactions that are cheap, clean and use less energy. For that, multicomponent reactions are drawing attention, yet, actual methods involve complicated work-ups, hazardous solvents, toxic catalysts, high catalyst loads, harsh reaction conditions and tedious catalyst preparation. Here, we demonstrate that the commercially available reagent, 9-mesityl-10 methylacridinium perchlorate (Acr+-Mes ClO4−), can serve as a photocatalyst in the presence of a blue lamp light source, promoting the synthesis of 2-amino-4H-chromenes via a multicomponent reaction with low catalyst loadings. A wide range of aromatic aldehydes readily undergo condensation with malononitrile and ArOH-type structural motifs under mild conditions to afford the products in 76–95% yield within 60 min. Keywords Green synthesis · Photocatalysis · Multicomponent reaction · Chromenes · Phenol moieties · Six member O-heterocycles
Introduction Chromenes and derivatives are an important series of oxygen-containing six-membered-ring heterocycles, which appear widely in a large number of natural compounds. Their synthesis has attracted considerable attention in the past decades due to their diverse biological and pharmaceutical activities (Desimoni et al. 2018). Generally, isolation from various medicinal plants or preparation from basic chemical materials with high chemselectivity is required to synthesize particular chromene derivatives. Such compounds are employed as antiproliferative and anticancer agents (Bonsignore et al. 1993; Amr et al. 2006), anti-HIV drugs (Rueping et al. 2008), anti-rheumatic drugs (Smith et al. 1995), xanthine oxidase inhibitors (Kaur et al. 2015), Electronic supplementary material The online version of this article (https://doi.org/10.1007/s10311-020-01053-2) contains supplementary material, which is available to authorized users. * Lu Chen [email protected] * Wei Yang [email protected] 1
School of Biotechnology and Health Science, Wuyi University, Jiangmen, China
School of Chemistry and Chemical Engineering, Guangzhou University, Guangzhou, China
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acetylcholinesterase inhibitors (Khoobi et al. 2013) and antimicrobial agents (Hostetler et al. 2014; Morgan et al. 2002) (Fig. 1). Multicomponent reactions (MCRs) are an excellent methodology for the synthesis of useful intermediates of biologically active molecules and have attracted increasing attention (Dömling et al. 2012; Wu et al. 2019). Drug discovery and screening using multicomponent reactions offer great potential. Use of multicomponent reactions minimizes the formation of by-products and development costs based on the consideration of green and sustainable chemistry (Horváth and Anastas 2007; Sheldon and Woodley 2018). With the rapid development of multicompone
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