10.1002/ejoc.202000257
European Journal of Organic Chemistry
COMMUNICATION
[8]
[9]
R. D. Smyth, J. K. Lee, A. Polk, P. B. Chemburkar, A. M. Savacool, J.
Clin. Phamacol. 1973, 13, 391-400.
M. H. Yen, J. R. Sheu, I. H. Peng, Y. M. Lee, J. W. Chern, J. Pharm.
Pharmacol. 1996, 48, 90-95.
[10]
[11]
M. Decker, Eur. J. Med. Chem. 2005, 40, 305-313.
a) D. R. Palo, R. A. Dagle, J. D. Holladay, Chem. Rev. 2007, 107, 3992-
4021; b) P. Anastas, N. Eghbali, Chem. Soc. Rev. 2010, 39, 301-312; c)
J.-P. Lange, Catal. Today 2001, 64, 3-8; d) C. Ge, X. Sang, W. Yao, L.
Zhang, D. Wang, Green Chem. 2018, 20, 1805-1812; e) D. Wang, K.
Zhao, C. Xu, H. Miao, Y. Ding, ACS Catal. 2014, 4, 3910-3918; f) D. Ye,
R. Huang, H. Zhu, L.-H. Zou, D. Wang, Org. Chem. Front. 2019, 6, 62-
69; g) Q. Wu, L. Pan, G. Du, C. Zhang, D. Wang, Org. Chem. Front.
2018, 5, 2668-2675; h) L. Wang, Y.-B. Xie, N.-Y. Huang, N.-N. Zhang,
D.-J. Li, Y.-L. Hu, M.-G. Liu, D.-S. Li, Adv. Synth. Catal. 2017, 359, 779-
785; i) L. Wang, Y.-B. Xie, N.-Y. Huang, J.-Y. Yan, W.-M. Hu, M.-G. Liu,
M.-W. Ding, ACS Catal. 2016, 6, 4010-4016.
[12]
[13]
a) T. T. Dang, B. Ramalingam, A. M. Seayad, ACS Catal. 2015, 5, 4082-
4088; b) F. Li, J. Xie, H. Shan, C. Sun, L. Chen, RSC Adv. 2012, 2, 8645-
8652.
a) K. Natte, H. Neumann, M. Beller, R. V. Jagadeesh, Angew. Chem. Int.
Edit. 2017, 56, 6384-6394; b) S. Ogawa, Y. Obora, Chem. Commun.
2014, 50, 2491-2493; c) L. K. M. Chan, D. L. Poole, D. Shen, M. P. Healy,
T. J. Donohoe, Angew. Chem. Int. Edit. 2014, 53, 761-765; d) X. Quan,
S. Kerdphon, P. G. Andersson, Chem. Eur. J. 2015, 21, 3576-3579.
a) B. Kang, S. H. Hong, Adv. Synth. Catal. 2015, 357, 834-840; b) S. H.
Kim, S. H. Hong, Org. Lett. 2016, 18, 212-215.
[14]
Scheme 4. Supporting experiments for the proposed mechanism
[15]
[16]
F. Li, L. Lu, P. Liu, Org. Lett. 2016, 18, 2580-2583.
G. Satish, A. Polu, L. Kota, A. Ilangovan, Org. Biomol. Chem. 2019, 17,
4774-4782.
CONCLUSION
[17]
Y. Hu, S. Li, H. Li, Y. Li, J. Li, C. Duanmu, B. Li, Org. Chem. Front. 2019,
6, 2744-2748.
In summary, we have successfully developed an easy and
efficient method for the synthesis of quinazolinones from 2-
aminobenzamides using methanol as the C1-source. This one pot
reaction for the synthesis of heterocycles was catalyzed using the
relatively inexpensive commercially available Cu(OAc)2.H2O
catalyst. This catalytic system afforded the desired products in
moderate to high isolated yields of up to 99%.
Acknowledgements
Faculty of Science, Naresuan University Research Grant
(R2562E037) supported this work. Additionally, we also thank the
Material Science Research Center (MsRC), Faculty of Science,
Chiang Mai University for financial support.
Keywords: Copper catalyst • quinazolinone • methanol
[1]
a) Y. Qiu, Y. Zhang, L. Jin, L. Pan, G. Du, D. Ye, D. Wang, Org. Chem.
Front. 2019, 6, 3420-3427; b) Z. Xu, D.-S. Wang, X. Yu, Y. Yang, D.
Wang, Adv. Synth. Catal. 2017, 359, 3332-3340; c) W. Yao, Z.-C. Duan,
Y. Zhang, X. Sang, X.-F. Xia, D. Wang, Adv. Synth. Catal. 2019, 361,
5695-5703; d) Z. Xu, X. Yu, X. Sang, D. Wang, Green Chem. 2018, 20,
2571-2577; e) Q. Yang, Y. Zhang, W. Zeng, Z.-C. Duan, X. Sang, D.
Wang, Green Chem. 2019, 21, 5683-5690; f) W. Hu, Y. Zhang, H. Zhu,
D. Ye, D. Wang, Green Chem. 2019, 21, 5345-5351; g) X. Sang, X. Hu,
R. Tao, Y. Zhang, H. Zhu, D. Wang, ChemPlusChem. 2020, 85, 123-
129.
[2]
[3]
X. Liu, H. Fu, Y. Jiang, Y. Zhao, Angew. Chem. Int. Edit. 2009, 48, 348-
351.
a) J. P. Michael, Nat. Prod. Rep. 2007, 24, 223-246; b) S. B. Mhaske, N.
P. Argade, Tetrahedron 2006, 62, 9787-9826; c) U. A. Kshirsagar, Org.
Biomol. Chem. 2015, 13, 9336-9352.
[4]
P.-P. Kung, M. D. Casper, K. L. Cook, L. Wilson-Lingardo, L. M. Risen,
T. A. Vickers, R. Ranken, L. B. Blyn, J. R. Wyatt, P. D. Cook, D. J. Ecker,
J. Med. Chem. 1999, 42, 4705-4713.
[5]
[6]
K.-i. Ozaki, Y. Yamada, T. Oine, T. Ishizuka, Y. Iwasawa, J. Med. Chem.
1985, 28, 568-576.
M. S. Sundrud, S. B. Koralov, M. Feuerer, D. P. Calado, A. E. Kozhaya,
A. Rhule-Smith, R. E. Lefebvre, D. Unutmaz, R. Mazitschek, H. Waldner,
M. Whitman, T. Keller, A. Rao, Science 2009, 324, 1334-1338.
a) S.-L. Cao, Y.-P. Feng, Y.-Y. Jiang, S.-Y. Liu, G.-Y. Ding, R.-T. Li,
Bioorg. Med. Chem. Lett. 2005, 15, 1915-1917; b) P. M. Chandrika, T.
Yakaiah, A. R. R. Rao, B. Narsaiah, N. C. Reddy, V. Sridhar, J. V. Rao,
Eur. J. Med. Chem. 2008, 43, 846-852; c) Y. Takase, T. Saeki, N.
Watanabe, H. Adachi, S. Souda, I. Saito, J. Med. Chem. 1994, 37, 2106-
2111.
[7]
3
This article is protected by copyright. All rights reserved.