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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
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
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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References
- 1 Alvarez-Builla J, Vaquero JJ, Barluenga J. Modern Heterocyclic Chemistry . Wiley-VCH; Weinheim: 2011
- 2 Li C.-J, Trost BM. Proc. Natl. Acad. Sci. U.S.A. 2008; 105: 13197
- 3a Song G, Wangw F, Li X. Chem. Soc. Rev. 2012; 41: 3651
- 3b Vidal X, Mascareñas JL, Gulías M. Org. Lett. 2021; 23: 5323
- 3c Gulías M, Mascareñas JL. Angew. Chem. Int. Ed. 2016; 55: 11000
- 3d Zhang F, Xin L, Yu Y, Liao S, Huang X. Synthesis 2021; 53: 238
- 4a Li B, Ali AI. M, Ge H. Chem 2020; 6: 2591
- 4b Lyons TW, Sanford MS. Chem. Rev. 2010; 110: 1147
- 4c Yang Y.-F, She Y. Int. J. Quantum Chem. 2018; e25723
- 4d Chen X, Engle KM, Wang D.-H, Yu J.-Q. Angew. Chem. Int. Ed. 2009; 48: 5094
- 4e Yun Y.-l, Yang J, Miao Y.-h, Sun J, Wang X.-j. J. Saudi Chem. Soc. 2020; 24: 151
- 4f Lyons TW, Sanford MS. Chem. Rev. 2010; 110: 1147
- 5 Shi Z, Zhang C, Li S, Pan D, Ding S, Cui Y, Jiao N. Angew. Chem. Int. Ed. 2009; 48: 4572
- 6 Zhang N, Li B, Zhong H, Huang J. Org. Biomol. Chem. 2012; 10: 9429
- 7 Zhong H, Yang D, Wang S, Huang J. Chem. Commun. 2012; 48: 3236
- 8 Wang L, Huang J, Peng S, Liu H, Jiang X, Wang J. Angew. Chem. Int. Ed. 2013; 52: 1768
- 9 Zhao M.-N, Ren Z.-H, Wang Y.-Y, Guan Z.-H. Org. Lett. 2014; 16: 608
- 10 Kaur M, Garg S, Malhi DS, Sohal HS. Curr. Org. Chem. 2021; 25: 449
- 11 Glavaski-Joksimovic A, Jeftinija K, Jeremic A, Anderson LL, Jeftinija S. J. Endocrinol. 2002; 175: 625
- 12 Yeo M, Chen Y, Jiang C, Chen G, Wang K, Chandra S, Bortsov A, Lioudyno M, Zeng Q, Wang P, Wang Z, Busciglio J, Ji R.-R, Liedtke W. Nat. Commun. 2021; 12: 6208
- 13a Peyronnet B, Brucker BM, Michel MC. Eur. Urol. Focus 2018; 4: 17
- 13b WHO Drug Inf. 2020; 34: 734
- 14 Stompór T, Napora M, Olszewski A. Expert Rev. Cardiovasc. Ther. 2011; 9: 663
- 15 Chebib FT, Perrone RD, Chapman AB, Dahl NK, Harris PC, Mrug M, Mustafa RA, Rastogi A, Watnick T, Yu AS. L, Torres VE. J. Am. Soc. Nephrol. 2018; 29: 2458
- 16a Li D, Park Y, Yoon W, Yun H, Yun J. Org. Lett. 2019; 21: 9699
- 16b Shi Q, Liao Z, Liu Z, Wen J, Li C, He J, Deng J, Cen S, Cao T, Zhou J, Zhu S. Nat. Commun. 2022; 13: 4402
- 16c Meyer AG, Smith JA, Hyland C, Williams CC, Bissember AC, Nicholls TP. Progr. Heterocycl. Chem. 2016; 28: 579
- 17 Filatov AS, Larina AG, Petrov ML, Boitsov VM, Stepakov AV. Synthesis 2022; 54: 2395
- 18 CCDC 2255818 (3aa) and 2255819 (5) contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures .
- 19 Albers P, Pietsch J, Parker SF. J. Mol. Catal. A, Chem. 2001; 173: 275
- 20 Pronina JA, Komolova DD, Boitsov VM, Stepakov AV, Selivanov SI. Appl. Magn. Reson. 2022; 53: 1677
- 21a Dardonville C, Jimeno ML, Alkorta I, Elguero J. ARKIVOC 2004; (ii): 206
- 21b Clayton MD, Marcinow Z, Rabideau PW. Tetrahedron Lett. 1998; 39: 9127
- 22a Azizian J, Mohammadi AA, Karimi AR. Synth. Commun. 2003; 33: 415
- 22b Mohammadi AA. J. Heterocycl. Chem. 2017; 54: 2075
- 23 Xue P, Ding J, Shen Y, Gao H, Zhao J, Sun J, Lu R. J. Mater. Chem. C. 2017; 5: 11532
- 24 Cossi M, Rega N, Scalmani G, Barone V. J. Comput. Chem. 2003; 24: 669
- 25 Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam NJ, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas Ő, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ. Gaussian 09, Revision C.01 . Gaussian; Wallingford CT: 2013