Citation: Wan Linxi, Gao Feng, Chen Wei, Zhou Xianli. One-Pot Synthesis of 2-((2-Aminobenzoyl)amino)benzoic Acid Derivatives[J]. Chinese Journal of Organic Chemistry, ;2019, 39(8): 2270-2276. doi: 10.6023/cjoc201902029 shu

One-Pot Synthesis of 2-((2-Aminobenzoyl)amino)benzoic Acid Derivatives

Wan Linxi ^a,b ,
Gao Feng ^a ,
Chen Wei ^a,, ,
Zhou Xianli ^a,b,,

a.
School of Life Science and Engineering, Southwest Jiaotong University, Chengdu 610031
b.
Key Laboratory of Advanced Technology of Materials, Ministry of Education, Southwest Jiaotong University, Chengdu 610031

Corresponding author: Chen Wei, chenweicstq@163.com Zhou Xianli, zhouxl@swjtu.edu.cn
Received Date: 25 February 2019
Revised Date: 17 April 2019
Available Online: 10 August 2019
Fund Project: Project supported by the National Natural Science Foundation of China (No. 81773605), the Science and Technology Project of Sichuan Province (No.2018JY0077), and the Interdisciplinary Frontier Basic Research Project of Southwest Jiaotong University (No. 2682017QY04)the Interdisciplinary Frontier Basic Research Project of Southwest Jiaotong University 2682017QY04the Science and Technology Project of Sichuan Province 2018JY0077the National Natural Science Foundation of China 81773605

Figures(3)

An efficient and one-pot method for the preparation of 2-((2-aminobenzoyl)amino)benzoic acid derivatives has been reported. Twenty 2-((2-aminobenzoyl)amino)benzoic acid derivatives were prepared with 84%~99% yields and nine compounds are new compounds. The effects of electron effect and steric hindrance on the reaction were discussed. It provides an operationally simple, environmentally friendly, high yield and good substrate universality method for the synthesis of 2-(2-aminobenzamide)benzoic acid derivatives. Furthermore, macrolide 4 and quinazolinone 5 can be synthesized from 2-((2-ami-nobenzoyl)amino)benzoic acid (3a) in one-step over 92% yields.
- 2-((2-aminobenzoyl) amino) benzoic acid,
- 2-aminobenzoic acid,
- one-pot synthesis
1. [1]
  Zhang, X.; Dong, S.; Fan, X.; Zhang, G. Prog. Chem. 2017, 29, 1351(in Chinese).
2. [2]
  Gurulingappa, H.; Amador, M. L.; Zhao, M.; Rudek, M. A.; Hidalgo, M.; Khan, S. R. Bioorg. Med. Chem. 2004, 14, 2213. doi: 10.1016/j.bmcl.2004.02.019
3. [3]
  Labrie, P.; Maddaford, S. P.; Fortin, S.; Rakhit, S.; Kotra, L. P.; Gaudreault, R. C. J. Med. Chem. 2006, 49, 7646. doi: 10.1021/jm060239b
4. [4]
  Shoji, N.; Umeyama, A.; Iuchi, A.; Saito, N.; Takemoto, T.; Nomoto, K.; Ohizumi, Y. J. Nat. Prod. 1988, 51, 791. doi: 10.1021/np50058a026
5. [5]
  Kukar, T.; Murphy, M. P.; Eriksen, J. L.; Sagi, S. A.; Weggen, S.; Smith, T. E.; Ladd, T.; Khan, M. A.; Kache, R.; Beard, J.; Dodson, M.; Merit, S.; Ozols, V. V.; Anastasiadis, P. Z.; Das, P.; Fauq, A.; Koo, E. H.; Golde, T. E. Nat. Med. 2005, 11, 545. doi: 10.1038/nm1235
6. [6]
  Narsinghani, T.; Chaturvedi, S. C. Bioorg. Med. Chem. Lett. 2006, 16, 461. doi: 10.1016/j.bmcl.2005.07.067
7. [7]
  Englund, E. E.; Neumann, S.; Eliseeva, E.; McCoy, J. G.; Titus, S.; Zheng, W.; Southall, N.; Shin, P.; Thomas, C. J.; Inglese, J.; Austin, C. P.; ershengorn, M. C.; Huang, W. M. MedChemComm 2011, 2, 1016. doi: 10.1039/c1md00145k
8. [8]
  Joubert, J.; Van, Dyk, S.; Green, I. R.; Malan, S. F. Bioorg. Med. Chem. 2011, 19, 3935. doi: 10.1016/j.bmc.2011.05.034
9. [9]
  Van, Straten, N. C. R.; Schoonus, Gerritsma, G. G.; Van, Someren, R. G.; Draaijer, J.; Adang, A. E. P.; Timmers, C. M.; Hanssen, R. G. J. M.; Van, Boeckel, C. A. A. ChemBioChem 2002, 3, 1023. doi: 10.1002/1439-7633(20021004)3:10<1023::AID-CBIC1023>3.0.CO;2-9
10. [10]
  Verma, A.; Giridhar, R.; Kanhed, A.; Sinha, A.; Modh, P.; Yadav, M. R. ACS Med. Chem. Lett. 2015, 6, 226. doi: 10.1021/ml500493r
11. [11]
  Roy, K.; De, A. U.; Sengupta, C. Drug. Des. Discovery 2002, 18, 23.
12. [12]
  Wiesbrock, F.; Schmidbaur, H. J. Inorg. Biochem. 2004, 98, 473. doi: 10.1016/j.jinorgbio.2003.12.017
13. [13]
  Wang, Q.; Tan, C.; Chen, H. J. Phys. Chem. 2010, 114, 13879.
14. [14]
  Zhu, K.; Hao, J.; Zhang, C. RSC Adv. 2015, 5, 11132. doi: 10.1039/C4RA15765F
15. [15]
  Tseng, M.; Lai, C.; Chu, Y. ChemComm. 2009, 28, 445.
16. [16]
  Bergman, J.; Arewång, C.; Svensson, P. H. J. Org. Chem. 2014, 79, 9065. doi: 10.1021/jo501269f
17. [17]
  Devi, R. V.; Garande, A. M.; Maity, D. K. J. Org. Chem. 2016, 81, 1689. doi: 10.1021/acs.joc.5b02327
18. [18]
  Witt, F. A.; Bergman, J. ChemInform 2002, 39, 351.
19. [19]
  Abdel-Hafez, A. M. Bioorg. Med. Chem. 2002, 10, 2297. doi: 10.1016/S0968-0896(02)00047-0
20. [20]
  Campbell, J. A.; Mcdougald, G.; Mcnab, H. ChemInform 2007, 20, 3179.
21. [21]
  Ferrand, G.; Dumas, H.; Depin, J. C.; Chavernac, G. Eur. J. Med. Chem. 1987, 22, 337.. doi: 10.1016/0223-5234(87)90272-8
22. [22]
  Tseng, M.; Yang, H.; Chu, Y. Org. Biomol. Chem. 2010, 8, 419. doi: 10.1039/B910545J
23. [23]
  Tseng, M.; Lai, C.; Chu, Y. Chem. Commun. 2009, 445.
24. [24]
  Kalusa, A.; Chessum, N.; Jones, K. Tetrahedron Lett. 2008, 49, 5840. doi: 10.1016/j.tetlet.2008.07.091
25. [25]
26. [26]
  Roell, D.; Rösler, T.; Hessenkemper, W.; Kraft, F.; Hauschilda, M.; Bartsch, S.; Abraham, T.; Houtsmuller, A.; Matuschc, R.; Royend, M.; Baniahmad, A. J. Steroid Biochem. 2019, 188, 59. doi: 10.1016/j.jsbmb.2018.12.005
27. [27]
  Mrs, S.; Satwant, K. J. Indian. Chem. Soc. 1976, 53, 382.
28. [28]
  Aridoss, G.; Laali, K. Eur. J. Org. Chem. 2011, 15, 2827.
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