An efficient and green synthesis of 2‐phenylquinazolin‐4(3H)‐ones using Brønsted acidic ionic liquid grafted onto silica

BACKGROUND The synthesis of 2‐phenylquinazolin‐4(3H)‐ones has been studied extensively, yet previous synthetic routes involved unrecyclable catalysts, toxic organic solvents and an expensive purification step with column chromatography. The current study reports on the preparation of 2‐phenylquinazo...

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Published in:Journal of chemical technology and biotechnology (1986) 2023-02, Vol.98 (2), p.555-565
Main Authors: Huynh, Tam Thanh Thi, Nguyen, The Thai, Tran, Phuong Hoang
Format: Article
Language:English
Subjects:
1‐methyl‐1‐(4‐sulfobutyl)pyrrolidinium hydrogen sulfate
2‐phenylquinazolin‐4(3H)‐one
acidic ionic liquid
Aldehydes
Catalysts
Chemical synthesis
Column chromatography
cyclization reaction
heterogeneous catalyst
Ionic liquids
Organic solvents
Recrystallization
Silica
Silica gel
Silicon dioxide
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Summary:BACKGROUND The synthesis of 2‐phenylquinazolin‐4(3H)‐ones has been studied extensively, yet previous synthetic routes involved unrecyclable catalysts, toxic organic solvents and an expensive purification step with column chromatography. The current study reports on the preparation of 2‐phenylquinazolin‐4(3H)‐ones from recyclable Brønsted acidic ionic liquid grafted onto silica. RESULTS 1‐Methyl‐1‐(4‐sulfobutyl)pyrrolidinium hydrogen sulfate supported onto silica gel (MSPHS@SiO2) was prepared via a simple process. This material was demonstrated as an effective recyclable catalyst for the preparation of 2‐phenylquinazolin‐4(3H)‐ones through the cyclization of 2‐aminobenzamide and aldehydes. The optimized conditions were MSPHS@SiO2 (30 mol%), TBHP (2 mmol), EtOH:H2O (15 mL, 1:2) at 120 °C for 24 h. A wide range of 2‐phenylquinazolin‐4(3H)‐ones were obtained in 34.2–92.5% yields via simple recrystallization. The catalyst could be recycled and a plausible mechanism is proposed. CONCLUSION MSPHS@SiO2 is an efficient and recyclable heterogeneous catalyst for the synthesis of 2‐phenylquinazolin‐4(3H)‐ones from readily available and low‐cost starting materials. © 2022 Society of Chemical Industry (SCI).
ISSN:0268-2575
1097-4660
DOI:10.1002/jctb.7271