Citation: Qu Renyu, Chen Nian, Liu Yuchao, Chen Qiong, Yang Guangfu. An Efficient Synthesis of Functionalized 6-Arylsubstituted Salicylates via Microwave Irradiation[J]. Chinese Journal of Organic Chemistry, ;2017, 37(5): 1266-1272. doi: 10.6023/cjoc201612049 shu

An Efficient Synthesis of Functionalized 6-Arylsubstituted Salicylates via Microwave Irradiation

Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079

Corresponding author: Yang Guangfu, gfyang@mail.ccnu.edu.cn
Received Date: 19 December 2016
Revised Date: 15 January 2017

Fund Project: and the National Natural Science Foundation of China 21372093the National Key Technologies R & D Program 2014BAD23B01Project supported by the Special Fund for Agroscientific Research in the Public Interest 201203022

Figures(1)

Functionalized 6-arylsalicylate substructures occur in a variety of pharmacologically relevant natural products and bioactive compounds. Especially 6-arylsubstituted salicylates, as a key pharmacophore of anti-resistant acetohydroxyacid synthase (AHAS) inhibitors have played a lead role in combatting the weed-resistance issues. Previously, we have explored two new methods to synthesize position-6 aryl substituted salicylic acid fragment. However, these two methods failed to introduce various substituents into salicylic acid. Here an efficient method for the synthesis of 6-substituted salicylates is described via a microwave-promoted Suzuki cross-coupling. Due to the obvious advantages of this method, such as a wide range of substrates, smooth and rapid reaction and moderate to excellent yields, this protocol could be utilized to synthesize more anti-resistant AHAS inhibitors.
- Functionalized 6-arylsalicylates,
- Suzuki cross-coupling reactions,
- Microwave irradiation,
- Electronic effect
1. [1]
  (a) Namki, C. ; Hee, J. Y. ; Hong, P. K. ; Sang, H. S. J. Nat. Prod. 2013, 76, 2291. (b) Gang, S. ; Wang, M. W. ; Welch, T. R. ; Blagg, B. S. J. J. Org. Chem. 2006, 71, 7618. (c) Delgado, E. J. J. Mol. Model. 2010, 16, 1421. (d) Abe, H. ; Nishioka, K. ; Takeda, S. ; Arai, M. ; Takeuchi, Y. ; Harayama, T. Tetrahedron Lett. 2005, 46, 3197. (e) Lin, C. N. ; Huang, P. L. ; Lu, C. M. ; Yen, M. H. , Wu, R. R. Phytochemistry 1997, 44, 1359. (f) Yang, G. F. ; Yang, H. Z. J. Cent. China Norm. Univ. , Nat. Sci. 2001, 35, 40 (in Chinese). (杨光富, 杨华铮, 华中师范大学学报(自然科学版), 2001, 35, 40. )(g) Yang, G. F. ; Liu, H. Y. ; Lu, R. J. ; Yang, H. Z. Chem. J. Chin. Univ. 1998, 19, 222 (in Chinese). (杨光富, 刘华银, 陆荣键, 杨华铮, 高等学校化学学报, 1998, 19, 222. )
2. [2]
  (a) He, Y. Z. ; Li, Y. X. ; Zhu, X. L. ; Yang, G. F. J. Chem. Inf. Model. 2007, 47, 2335. (b) Li, Y. X. ; Luo, Y. P. ; Xi, Z. ; Yang, G. F. J. Agric. Food Chem. 2006, 54, 9135. (c) Chen, C. N. ; Chen, Q. ; Liu, Y. C. ; Yang, G. F. Bioorg. Med. Chem. 2010, 18, 4897. (d) Xiong, Y. ; Liu, J. J. ; Yang, G. F. J. Comput. Chem. 2010, 31, 1592. (e) Chen, C. N. ; Lv, L. L. ; Ji, F. Q. ; Yang, G. F. Bioorg. Med. Chem. 2009, 17, 3011.
3. [3]
  (a) Ji, F. Q. ; Niu, C. W. ; Yang, G. F. ; Xi, Z. Chem. Med. Chem. 2008, 3, 1203. (b) Liu, Y. C. ; Qu, R. Y. ; Chen, Q. ; Yang, J. F. ; Niu, C. W. ; Xi, Z. ; Yang, G. F. J. Agric. Food Chem. 2016, 64, 4845. (c) Yang, G. F. ; Liu, Y. C. ; Chen, Q. ; Xi, Z. ; Niu, C. CN 104650084, 2015 [Chem. Abstr. 2015, 903779]. (d) Yang, G. F. ; Liu, Y. C. ; Chen, Q. CN 104140397, 2013[Chem. Abstr. 2014, 1908130].
4. [4]
  (a) Chan, T. H. ; Brownbridge, P. J. Am. Chem. Soc. 1980, 102, 3534. (b) Brownbridge, P. ; Chan, T. H. ; Brook, M. A. ; Kang, G. J. Can. J. Chem. 1983, 61, 688. (c) Feist, H. ; Langer, P. Synthesis 2007, 3, 327. (d) Stefan, B. ; Nazken, K. K. ; Zharylkasyn, A. A. ; Alexander, V. ; Peter, L. Tetrahedron 2012, 68, 3654. (e) Matthias, L. ; Muhammad, S. ; Alexander, V. ; Christine, F. ; Peter, L. Eur. J. Org. Chem. 2010, 5118. (f) Mohanad, S. ; Olumide, F. ; Abdolmajid, R. ; Mathias, L. ; Stefanie, R. ; Muhammad, S. ; Alexander, V. ; Christine, F. ; Peter, L. Eur. J. Org. Chem. 2010, 3732. (g) Ibrar, H. ; Mirza, A. Y. ; Matthias, L. ; Thomas, P. ; Christine, F. ; Helmar, G. ; Peter, L. Eur. J. Org. Chem. 2008, 503. (h) Satya, P. S. ; Rakesh, T. ; Akhilesh, K. V. Tetrahedron 2012, 68, 9035. (i) So, W. Y. ; Byung, S. K. ; Arun, R. J. J. Am. Chem. Soc. 2012, 134, 11308. (j) Hao, X. ; Shang, f. L. ; Hong, X. L. ; Hua, F. ; Yu, Y. J. Chem. Commun. 2010, 7617. (k) Patricia, G. ; Manuel, A. ; Fernndez, R. ; Enrique, A. Angew. Chem. , Int. Ed. 2009, 48, 5534.
5. [5]
  (a) Liu, Y. C. ; Huang, Z. Y. ; Chen, Q. ; Yang, G. F. Tetrahedron 2013, 69, 9025. (b) Qu, R. Y. ; Liu, Y. C. ; Wu, Q. Y. ; Chen, Q. ; Yang, G. F. Tetrahedron 2015, 71, 8123.
6. [6]
  (a) Leadbeater, N. E. Chem. Commun. 2005, 2881. (b) Lussier, T; Herve, G; Enderlin, G; Len, C. RSC Adv. 2014, 4, 462183. (c) Kappe, C. O. Angew. Chem. , Int. Ed. 2004, 43, 6250. (d) Zhou, Z. Z. ; Zhao, P. L. ; Huang, W. ; Yang, G. F. Adv. Synth. Catal. 2006, 348, 63. (e) Zhou, Z. Z. ; Ji, F. Q. ; Cao, M. ; Yang, G. F. Adv. Synth. Catal. 2006, 348, 1826. (f) Liu, Y. C. ; Ye, C. J. ; Chen, Q. ; Yang, G. F. Tetrahedron Lett. 2013, 54, 949. (g) Liu, Y. C. ; Qu, R. Y. ; Chen, Q. ; Yang, G. F. Tetrahedron 2014, 70, 2746. (h) Hua, C. ; Wu, Q. Y. ; Han, F. ; Yang, G. F. Chin. Chem. Lett. 2014, 25, 705.
7. [7]
  Mei, T. S.; Giri, R.; Maugel, N.; Yu, J. Q. Angew. Chem., Int. Ed. 2008, 47, 5215. doi: 10.1002/anie.v47:28
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