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Synthesis 2022; 54(01): 210-216
DOI: 10.1055/a-1577-6344
DOI: 10.1055/a-1577-6344
paper
Mn(OAc)3 Induced C-4 Arylations of Quinazoline 3-Oxides with Arylboronic Acids
Bursa Uludağ University Research Fund is gratefully acknowledged for its financial support (Project No: DDP(F)-2020/6).
Abstract
The use of manganese triacetate as an oxidant component in the C-4 arylations of 2-aryl-quinazoline 3-oxides with arylboronic acids is reported. The new protocol was applied to prepare new 2,4-diarylated quinazoline 3-oxides in good to high yields. The method was shown to tolerate various substituents on both aromatic rings, and no complications such as deoxygenation or rearrangement to quinazolin-4(3H)-one was observed.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1577-6344.
- Supporting Information
Publikationsverlauf
Eingereicht: 12. Juli 2021
Angenommen nach Revision: 03. August 2021
Accepted Manuscript online:
03. August 2021
Artikel online veröffentlicht:
01. September 2021
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References
- 1 Shang XF, Morris-Natschke SL, Liu YQ, Guo X, Xu XS, Goto M, Li JC, Yang GZ, Lee KH. Med. Res. Rev. 2018; 38: 775
- 2 Auti PS, George G, Paul AT. RSC Adv. 2020; 10: 41353
- 3 Hameed A, Al-Rashida M, Uroos M, Ali SA, Arshia, Ishtiaq M, Khan KM. Expert Opin. Ther. Pat. 2018; 28: 281
- 4 Bhatia P, Sharma V, Alam O, Manaithiya A, Alam P, Kahksha, Alam MT, Imran M. Eur. J. Med. Chem. 2020; 204: 112640
- 5 Shagufta, Ahmad I. Med. Chem. Commun. 2017; 8: 871
- 6 Khan I, Ibrar A, Ahmed W, Saeed A. Eur. J. Med. Chem. 2015; 90: 124
- 7 Gandeepan P, Müller T, Zell D, Cera G, Warratz S, Ackermann L. Chem. Rev. 2019; 119: 2192
- 8 Ackermann L. Acc. Chem. Res. 2020; 53: 84
- 9 Zhao Q, Meng G, Nolan SP, Szostak M. Chem. Rev. 2020; 120: 1981
- 10 Chen Z, Wang B, Zhang J, Yu W, Liu Z, Zhang Y. Org. Chem. Front. 2015; 2: 1107
- 11 Asensio JM, Bouzouita D, Van Leeuwen PW. N. M, Chaudret B. Chem. Rev. 2020; 120: 1042
- 12 Ackermann L, Bellina F, Bruneau C, Carr KJ. T, Chang S, Dana S, De Sarkar S, Dixneuf PH, Doucet H, Glorius F, Kim JG, Li J, Macgregor SA, McMullin CL, Patureau FW, Sahoo AK, Shin K, Soulé J.-F, Yadav MR, Wang G.-W, Wencel-Delord J. C–H Bond Activation and Catalytic Functionalization II, Vol. 56. Dixneuf PH, Doucet H. Springer International; Switzerland: 2016
- 13 Shen Y, Chen J, Liu M, Ding J, Gao W, Huang X, Wu H. Chem. Commun. 2014; 50: 4292
- 14 Yuan JW, Qu LB. Chin. Chem. Lett. 2017; 28: 981
- 15 Bering L, Antonchick AP. Org. Lett. 2015; 17: 3134
- 16 Mai W, Yuan J, Li Z, Sun G, Qu L. Synlett 2012; 23: 145
- 17 Fan L, Wang T, Tian Y, Xiong F, Wu S, Liang Q, Zhao J. Chem. Commun. 2016; 52: 5375
- 18 Yang Q, Lou M, Yin Z, Deng Z, Ding Q, Peng Y. Org. Biomol. Chem. 2018; 16: 8724
- 19 Fan L, Zhang Z, Wang T, Liang Q, Zhao J. Org. Chem. Front. 2018; 5: 2492
- 20 Yang Q, Yin Z, Zheng L, Yuan J, Wei S, Ding Q, Peng Y. RSC Adv. 2019; 9: 5870
- 21 Ramesh B, Reddy CR, Kumar GR, Reddy BV. S. Tetrahedron Lett. 2018; 59: 628
- 22 Lv W, Zeng Y, Zhang S, Li Q, Wang H. Org. Lett. 2015; 17: 2972
- 23 Coşkun N, Çetin M. Tetrahedron Lett. 2004; 45: 8973
- 24 Coşkun N, Çetin M. Tetrahedron 2007; 63: 2966
- 25 Samandram R, Korukçu MC, Coşkun N. Synth. Commun. 2021; 51: 2349
- 26 Zhu J, Shao Y, Hu K, Qi L, Cheng T, Chen J. Org. Biomol. Chem. 2018; 16: 8596
- 27 Yan Y, Shi M, Niu B, Meng X, Zhu C, Liu G, Chen T, Liu Y. RSC Adv. 2016; 6: 36192
- 28 Liu Q, Zhao Y, Fu H, Cheng C. Synlett 2013; 2089
- 29 Mohammed S, Vishwakarma RA, Bharate SB. J. Org. Chem. 2015; 80: 6915
- 30 Ye X, Chen Z, Zhang Z, Fu Y, Deng Z, Peng Y. Can. J. Chem. 2019; 97: 682
- 31 Dwivedi S, Bardhan S, Ghosh P, Das S. RSC Adv. 2014; 4: 41045