One-pot Synthesis of a New Category of 2-aryl-quinazolinones Using OImDSA as an Efficient Heterocyclic Medium

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Author(s): Abdolrahman Keyhani, Mohammad Nikpassand*, Leila Zare Fekri, Hassan Kefayati

Journal Name: Combinatorial Chemistry & High Throughput Screening
Accelerated Technologies for Biotechnology, Bioassays, Medicinal Chemistry and Natural Products Research


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Abstract:

Background: Dihydroquinazolinone derivatives are an important family of fused heterocyclic shows a wide range of biological, medicinal and pharmacological properties such as anti-tumor, anti-biotic, diuretic, analgesic, antihypertonic, anti-pyretic, anti-depressant, anti-histamine and vasodilation activities.

Introduction: So far some acid catalysts, e.g.; p-toluenesulfonic acid, silica sulfuric acid, zinc(II) perfluorooctanoate, gallium(III) triflate, ionic liquid, Al(H2PO4)3, I2, montmorillonite K-10, Amberlyst-15, Al/Al2O3 and Fe3O4 nanoparticles, have been reported to accomplish this three component reaction. Some of these methods have drawbacks such as toxic solvents and catalysts, long reaction time, the use of expensive catalysts and adverse yields.

Method: A mixture of benzaldehydes (1mmol), isatoic anhydride (1 mmol), Glycine (1 mmol) and OImDSA (2 mL) were stirred at room temperature for the required reaction times (1-2 h). The progress of the reaction was monitored by TLC (EtOAc: petroleum ether 1:2). After completion of reaction, as indicated by TLC, the ionic liquid was separated by extraction with 2×15 mL of water. The solid residue was separated by recrystallization from EtOH. The pure products were collected in 86-97% yields.

Results: Herein, in order to achieve a more efficient synthesis method, to deplete side effects, reduce reaction steps, increase efficiency and curtail reaction time, and also to continue our research on the synthesis of heterocyclic and pharmaceutical compounds. We wish to report the mild synthesis of some derivatives of 2-aryl-quinazolin-4(1H)-ones from isatoic anhydride and Glycine using OImDSA

Conclusion: In conclusion, we have developed a simple, green and efficient protocol for the synthesis of 2-aryl-quinazolin- 4(1H)-ones using OImDSA as an efficient and new procedure. Simplicity, easy practice, integrated with inexpensive, environmentally friendly and reusable ionic liquid are notable attributes of this new method. To the best of our knowledge, this is the first report for the synthesis of a new library of quinazolin-4(1H)-ones derived from Glycine as a natural substrate based on green chemistry conditions.

Keywords: one-pot reaction, 2-aryl-quinazolin-4(1H)-one, Glycine, ionic liquid, synthesis, isatoic anhydride

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(E-pub Ahead of Print)
DOI: 10.2174/1386207324999210120194730
Price: $95

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