Catalyst- and solvent-free coupling of 2-methyl quinazolinones and 3-(trifluoroacetyl)coumarins: An environmentally benign access of quinazolinone derivatives

An environmentally benign highly atom-economic protocol for the construction of the CAC bond has been developed under catalyst-and solvent-free conditions. This protocol involves the efficient coupling of 2-methyl quinazolinones with 3-(trifluoroacetyl)coumarins for the access of quinazolinone derivatives in excellent yields (up to 90 %). The crystal structure of compound 3di was investigated by X-ray diffraction analysis. The biological activities, such as in vitro antifungal activity of the quinazolinone derivatives against Fusarium graminearum, Fusarium moniliforme, Fusarium oxysporum, Phytophthora parasitica var nicotianae, and Rhizoctonia solani Kuhn, were investigated. The bioassay results indicated that most of the target products exhibited promising fungicidal activities, and compound 3 cl exhibited 95 % fungicidal activity against R. solani, with an EC50 value of 10.6 lg/mL.(c) 2023 Published by Elsevier B.V. on behalf of King Saud University. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).

Automated summary

An environmentally friendly approach for constructing the CAC bond using catalyst- and solvent-free conditions was developed. This method involves the efficient coupling of 2-methyl quinazolinones with 3-(trifluoroacetyl)coumarins to produce quinazolinone derivatives with excellent yields (up to 90%). The biological activities of these derivatives against various fungal strains were investigated, showing promising fungicidal activities for most of the target products, with compound 3 cl exhibiting 95% fungicidal activity against R. solani with an EC50 value of 10.6 lg/mL.