Efficient synthesis of 4‐phenacylideneflavenes using recyclable gelified <scp>B</scp>rønsted acidic ionic liquid under solvent‐free and column chromatography‐free conditions: a green method and mechanistic insight

Journal of Chemical Technology and Biotechnology - Tập 97 Số 3 - Trang 653-661 - 2022
Xuan‐Trang Thi Nguyen1,2, The Thai Nguyen1,2, Long Hoàng Nguyễn1,2, Hai Truong Nguyen1,2, Phuong Hoang Tran1,2
1Department of Organic Chemistry, Faculty of Chemistry, University of Science, Ho Chi Minh City, Vietnam
2Vietnam National University, Ho Chi Minh City, Vietnam

Tóm tắt

AbstractBACKGROUNDSynthetic routes involving recyclable catalysts, solvent‐free conditions and chromatography‐free purification are becoming more popular as favorable substitutes for conventional ones. We report here the exciting possibility of producing selective functionalization of 4‐phenacylideneflavenes using an efficient gelified Brønsted acidic ionic liquid (BAIL) as a recyclable catalyst from available and cheap starting materials.RESULTSThis one‐pot cascade approach allowed the synthesis of various 4‐phenacylideneflavenes in good yields with operational simplicity and easy workup. Moreover, the condensation of salicylaldehyde and acetophenone on a gram scale gave the desired product in 78% yield using our optimized conditions. In addition, the reaction mechanism in which two crucial intermediates were identified using high‐resolution electrospray ionization mass spectrometry was also proposed in the present work.CONCLUSIONThis method represents the first example of using BAIL gel recyclable catalyst in a straight and clean synthesis of various 4‐phenacylideneflavenes from cheap and available starting materials, namely acetophenones and salicylaldehyde. © 2021 Society of Chemical Industry (SCI).

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Journal of Chemical Technology and Biotechnology

Tập 97 Số 3

653-661

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