Palladium-Catalyzed Oxidative Cycloaddition of Quinazoline-2,4(1H,3H)-diones and Diarylalkynes via C–H/N–H Activation

Darya D. Komolova; Yulia A. Pronina; Stanislav V. Lozovskiy; Stanislav I. Selivanov; Alexander I. Ponyaev; Alexander S. Filatov; Vitali M. Boitsov; Alexander V. Stepakov

doi:10.1055/a-2105-2850

Synthesis, Inhaltsverzeichnis

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

^aSaint-Petersburg State University, Universitetskaya nab. 7/9, 199034 St. Petersburg, Russian Federation

,

Yulia A. Pronina

^bSaint-Petersburg State Institute of Technology, Moskovskii pr. 26, 190013 St. Petersburg, Russian Federation

,

Stanislav V. Lozovskiy

^cCRAB, Case 551, Aix-Marseille Université, Avenue Escadrille Normandie-Niemen, 13397 Marseille, Cedex 20, France

^dInstitute of Organoelement compounds of Russian Academy of Sciences, Vavilova str. 28, 119334 Moscow, Russian Federation

,

Stanislav I. Selivanov

^eLaboratory of Biomolecular NMR, Saint-Petersburg State University, 199034 St. Petersburg, Russian Federation

^bSaint-Petersburg State Institute of Technology, Moskovskii pr. 26, 190013 St. Petersburg, Russian Federation

,

Alexander I. Ponyaev

^bSaint-Petersburg State Institute of Technology, Moskovskii pr. 26, 190013 St. Petersburg, Russian Federation

,

Alexander S. Filatov

^aSaint-Petersburg State University, Universitetskaya nab. 7/9, 199034 St. Petersburg, Russian Federation

,

Vitali M. Boitsov

^fSaint Petersburg National Research Academic University of the Russian Academy of Sciences, ul. Khlopina 8/3, 194021, St. Petersburg, Russian Federation

,

Alexander V. Stepakov∗

^aSaint-Petersburg State University, Universitetskaya nab. 7/9, 199034 St. Petersburg, Russian Federation

^bSaint-Petersburg State Institute of Technology, Moskovskii pr. 26, 190013 St. Petersburg, Russian Federation

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Abstract

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In commemoration of the 300^th 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 calculations

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