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Synthesis 2023; 55(23): 4034-4048
DOI: 10.1055/a-2105-2850
DOI: 10.1055/a-2105-2850
paper
Palladium-Catalyzed Oxidative Cycloaddition of Quinazoline-2,4(1H,3H)-diones and Diarylalkynes via C–H/N–H Activation
Authors
This work was supported by the Ministry of Science and Higher Education of the Russian Federation (state assignment FSEN-2023-0002). V.M.B. is grateful to the Ministry of Education and Science of the Russian Federation (project FSRM-2023-0005) for financial support. S.I.S. acknowledges Saint-Petersburg State University for a research grant 104236506.
In commemoration of the 300th anniversary of St Petersburg State University’s founding
Abstract
The oxidative cycloaddition of 3-subsituted quinazoline-2,4(1H,3H)-diones and alkynes has been developed. The reaction is Pd(II)-catalyzed and successfully occurs in the presence of Ag(I) oxidants. This transformation is assumed to proceed by N–H palladation of the quinazoline-2,4(1H,3H)-dione followed by ortho-C–H activation. Using this methodology, a series of 5,6,7,8-tetraaryl-1H-azepino[3,2,1-ij]quinazoline-1,3(2H)-diones were obtained in moderate to good yields. The resulting tricyclic heterocycles can be converted by alkaline hydrolysis into 1H-benzo[b]azepine-9-carboxamide derivatives. DFT calculations have been carried out to shed light on the reaction mechanism.
Key words
benzazepines - quinazolines - alkynes - C–H/N–H activation - palladium - oxidative cycloaddition - DFT calculationsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2105-2850.
- Supporting Information (PDF)
Publikationsverlauf
Eingereicht: 22. April 2023
Angenommen nach Revision: 02. Juni 2023
Accepted Manuscript online:
02. Juni 2023
Artikel online veröffentlicht:
04. Juli 2023
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