Metal-free synthesis of 1,1-dimethyl-2,2,2-trifluoroethyl substituted quinazolinones via tandem radical cyclization of quinazolin-4(3 H )-ones with 3,3,3-trifluoro-2,2-dimethylpropanoic acid

A metal-free (NH ) S O -mediated decarboxylative trifluoromethylation reaction of alkenes with 3,3,3-trifluoro-2,2-dimethylpropionic acid has been proposed. This method offers a novel route for the direct synthesis of a series of CMe CF -containing quinazolinones from basic chemical raw materials. T...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2024-08, Vol.22 (31), p.6376-6384
Main Authors: Gao, Shenyuan, Cai, Menglu, Wang, Xiaozhong, Jiang, Dapeng, Lin, Pen, Dai, Liyan
Format: Article
Language:English
Subjects:
Alkenes
Atom economy
Chemical synthesis
Oxidation
Quinazolinone
Quinazolinones
Raw materials
Reaction mechanisms
Substrates
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Summary:A metal-free (NH ) S O -mediated decarboxylative trifluoromethylation reaction of alkenes with 3,3,3-trifluoro-2,2-dimethylpropionic acid has been proposed. This method offers a novel route for the direct synthesis of a series of CMe CF -containing quinazolinones from basic chemical raw materials. The reaction mechanism was studied by a radical trapping test and DFT methods, verifying an oxidation-triggered cascade process promoted by the CMe CF radicals. This strategy provides advantages such as high yield, wide substrate compatibility, and high atom economy.
ISSN:1477-0520
1477-0539
1477-0539
DOI:10.1039/d4ob00914b