Articles

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

  • Wan Linxi ,
  • Gao Feng ,
  • Chen Wei ,
  • Zhou Xianli
Expand
  • 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

Received date: 2019-02-25

  Revised date: 2019-04-17

  Online published: 2019-05-10

Supported by

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).

Abstract

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.

Cite this article

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

References

[1] Zhang, X.; Dong, S.; Fan, X.; Zhang, G. Prog. Chem. 2017, 29, 1351(in Chinese). (张晓鹏,董淑祥,范学森,张贵生,化学进展, 2017, 29, 1351.)
[2] Gurulingappa, H.; Amador, M. L.; Zhao, M.; Rudek, M. A.; Hidalgo, M.; Khan, S. R. Bioorg. Med. Chem. 2004, 14, 2213.
[3] Labrie, P.; Maddaford, S. P.; Fortin, S.; Rakhit, S.; Kotra, L. P.; Gaudreault, R. C. J. Med. Chem. 2006, 49, 7646.
[4] Shoji, N.; Umeyama, A.; Iuchi, A.; Saito, N.; Takemoto, T.; Nomoto, K.; Ohizumi, Y. J. Nat. Prod. 1988, 51, 791.
[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.
[6] Narsinghani, T.; Chaturvedi, S. C. Bioorg. Med. Chem. Lett. 2006, 16, 461.
[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.
[8] Joubert, J.; Van, Dyk, S.; Green, I. R.; Malan, S. F. Bioorg. Med. Chem. 2011, 19, 3935.
[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.
[10] Verma, A.; Giridhar, R.; Kanhed, A.; Sinha, A.; Modh, P.; Yadav, M. R. ACS Med. Chem. Lett. 2015, 6, 226.
[11] Roy, K.; De, A. U.; Sengupta, C. Drug. Des. Discovery 2002, 18, 23.
[12] Wiesbrock, F.; Schmidbaur, H. J. Inorg. Biochem. 2004, 98, 473.
[13] Wang, Q.; Tan, C.; Chen, H. J. Phys. Chem. 2010, 114, 13879.
[14] Zhu, K.; Hao, J.; Zhang, C. RSC Adv. 2015, 5, 11132.
[15] Tseng, M.; Lai, C.; Chu, Y. ChemComm. 2009, 28, 445.
[16] Bergman, J.; Arewång, C.; Svensson, P. H. J. Org. Chem. 2014, 79, 9065.
[17] Devi, R. V.; Garande, A. M.; Maity, D. K. J. Org. Chem. 2016, 81, 1689.
[18] Witt, F. A.; Bergman, J. ChemInform 2002, 39, 351.
[19] Abdel-Hafez, A. M. Bioorg. Med. Chem. 2002, 10, 2297.
[20] Campbell, J. A.; Mcdougald, G.; Mcnab, H. ChemInform 2007, 20, 3179.
[21] Ferrand, G.; Dumas, H.; Depin, J. C.; Chavernac, G. Eur. J. Med. Chem. 1987, 22, 337..
[22] Tseng, M.; Yang, H.; Chu, Y. Org. Biomol. Chem. 2010, 8, 419.
[23] Tseng, M.; Lai, C.; Chu, Y. Chem. Commun. 2009, 445.
[24] Kalusa, A.; Chessum, N.; Jones, K. Tetrahedron Lett. 2008, 49, 5840.
[25] Öberg, C. T.; Strand, M.; Andersson, E. K. J. Med. Chem. 2012, 55, 3170.
[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.
[27] Mrs, S.; Satwant, K. J. Indian. Chem. Soc. 1976, 53, 382.
[28] Aridoss, G.; Laali, K. Eur. J. Org. Chem. 2011, 15, 2827.

Outlines

/