Synthesis 2023; 55(23): 4034-4048
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

Darya D. Komolova
a   Saint-Petersburg State University, Universitetskaya nab. 7/9, 199034 St. Petersburg, Russian Federation
,
Yulia A. Pronina
b   Saint-Petersburg State Institute of Technology, Moskovskii pr. 26, 190013 St. Petersburg, Russian Federation
,
Stanislav V. Lozovskiy
c   CRAB, Case 551, Aix-Marseille Université, Avenue Escadrille Normandie-Niemen, 13397 Marseille, Cedex 20, France
d   Institute of Organoelement compounds of Russian Academy of Sciences, Vavilova str. 28, 119334 Moscow, Russian Federation
,
Stanislav I. Selivanov
e   Laboratory of Biomolecular NMR, Saint-Petersburg State University, 199034 St. Petersburg, Russian Federation
b   Saint-Petersburg State Institute of Technology, Moskovskii pr. 26, 190013 St. Petersburg, Russian Federation
,
Alexander I. Ponyaev
b   Saint-Petersburg State Institute of Technology, Moskovskii pr. 26, 190013 St. Petersburg, Russian Federation
,
Alexander S. Filatov
a   Saint-Petersburg State University, Universitetskaya nab. 7/9, 199034 St. Petersburg, Russian Federation
,
Vitali M. Boitsov
f   Saint Petersburg National Research Academic University of the Russian Academy of Sciences, ul. Khlopina 8/3, 194021, St. Petersburg, Russian Federation
,
Alexander V. Stepakov
a   Saint-Petersburg State University, Universitetskaya nab. 7/9, 199034 St. Petersburg, Russian Federation
b   Saint-Petersburg State Institute of Technology, Moskovskii pr. 26, 190013 St. Petersburg, Russian Federation
› Author Affiliations
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.

Supporting Information



Publication History

Received: 22 April 2023

Accepted after revision: 02 June 2023

Accepted Manuscript online:
02 June 2023

Article published online:
04 July 2023

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