Citation: Liu Gaoxiaozheng, Wu Chao, Chen Bifeng, He Ru, Chen Chao. Concise synthesis of xanthones by the tandem etherification-Acylation of diaryliodonium salts with salicylates[J]. Chinese Chemical Letters, ;2018, 29(6): 985-988. doi: 10.1016/j.cclet.2017.11.046 shu

Concise synthesis of xanthones by the tandem etherification-Acylation of diaryliodonium salts with salicylates

Liu Gaoxiaozheng ^a,b ,
Wu Chao ^a,b ,
Chen Bifeng ^a ,
He Ru ^a ,
Chen Chao ^a,b,,

a.
MOE Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology, Department of Chemistry, Tsinghua University, Beijing 100084, China
b.
The Graduate School at Shenzhen, Tsinghua University, Beijing 100084, China

Corresponding author: Chen Chao, chenchao01@mails.tsinghua.edu.cn
Received Date: 20 September 2017
Revised Date: 26 November 2017
Accepted Date: 30 November 2017
Available Online: 2 June 2017

Figures(6)

An efficient synthetic method for multi-substituted xanthones was developed. The reaction of diaryliodonium salts and salicylates was employed for the preparation of the xanthones. This method proceeded through an intermolecular etherification-acylation to give target heterocycles in good yields (up to 91%). Multi-substituted xanthones were gained by shifting the substituent of salicylates or diaryliodonium salts.
- Xanthone,
- Diaryliodonium salts,
- Etherification,
- Acylaion,
- Multiple substituent
1. [1]
  (a) K. Masters, S. Brase, Chem. Rev. 112(2012) 3717-3776;
  (b) F. F. Zhong, Y. Chen, Z. N. Mei, G. Z. Yang, Chin. Chem. Lett. 18(2007) 849-851;
  (c) B. Lesch, S. Brase, Angew. Chem. Int. Ed. 43(2004) 115-118;
  (d) M. L. Cardona, M. I. Fernandez, J. R. Pedro, A. Serrano, Phytochemistry 29(1990) 3003-3006.
2. [2]
  (a) V. Peres, T. J. Nagem, F. F. Oliveira, Phytochemistry 55(2000) 683-710;
  (b) M. K. Schwaebe, T. J. Moran, J. P. Whitten, Tetrahedron Lett. 46(2005) 827-829;
  (c) M. Kenji, A. Yukihiro, Y. Hong, et al., Bioorg. Med. Chem. 12(2004) 5799-5806;
  (d) M. Pedro, F. Cerqueira, M. E. Sousa, M. S. J. Nascimento, M. Pinto, Bioorg. Med. Chem. 10(2002) 3725-3730;
  (e) M. H. Wang, L. Li, T. Jiang, et al., Chin. Chem. Lett. 26(2015) 1507-1510.
3. [3]
  (a) M. M. M. Pinto, M. E. Sousa, M. S. J. Nascimento, Curr. Med. Chem. 12(2005) 2517-2521;
  (b) W. Mahabusarakam, W. Nuangnaowarat, W. C. Taylor, Phytochemistry 67(2006) 470-474;
  (c) C. Gnerre, U. Thull, P. Gailland, et al., Helv. Chim. Acta 84(2001) 552-570.
4. [4]
  (a) J. Yang, D. Knueppel, B. Cheng, D. Mans, S. F. Martin, Org. Lett. 17(2015) 114-117;
  (b) M. Zhou, S. Ji, Z. Wu, et al., Eur. J. M. Chem. 96(2015) 92-94;
  (c) J. Kosin, N. Ruangrungsi, C. Ito, H. Furukawa, H. Phytochem. 47(1998) 1167-1168.
5. [5]
  (a) Zhang, R. Shi, P. Gan, et al., Angew. Chem. Int. Ed. 51(2012) 5204-5207;
  (b) S. Wertz, D. Leifert, A. Studer, Org. Lett. 15(2013) 928-931;
  (c) Y. Liu, L. Huang, F. Xie, Y. Hu, J. Org. Chem. 75(2010) 6304-6307;
  (e) M. E. Sousa, M. M. M. Pinto, Curr. Med. Chem. 12(2005) 2447-2451.
6. [6]
  (a) J. Zhao, R. C. Larock, J. Org. Chem. 72(2007) 583-588;
  (b) A. L. Nichols, P. Zhang, S. F. Martin, Org. Lett. 13(2011) 4696-4699;
  (c) C. A. Menendez, F. Nador, G. Radivoy, D. C. Gerbino, Org. Lett. 16(2014) 2846-2849.
7. [7]
  (a) E. A. Merritt, B. Olofsson, Angew. Chem. Int. Ed. 48(2009) 9052-9070;
  (b) V. V. Zhdankin, P. J. Stang, Chem. Rev. 108(2008) 5299-5358;
  (c) V. V. Zhdankin, P. J. Stang, Chem. Rev. 102(2002) 2523-2584;
  (d) V. V. Grushin, Chem. Soc. Rev. 29(2000) 315-324;
  (e) P. J. Stang, V. V. Zhdankin, Chem. Rev. 96(1996) 1123-1178.
8. [8]
  (a) X. Pang, C. Chen, X. Su, M. Li, L. Wen, Org. Lett. 16(2014) 6228-6231;
  (b) Y. Wang, C. Chen, J. Peng, M. Li, Angew. Chem. Int. Ed. 52(2013) 5323-5327;
  (c) X. Su, C. Chen, Y. Wang, et al., Chem. Commun. 49(2013) 6752-6754;
  (d) Y. Wang, C. Chen, S. Zhang, et al., Org. Lett. 15(2013) 4794-4797;
  (e) G. Wang, C. Chen, J. Peng, Chem. Commun. 52(2016) 10277-10280;
  (f) J. Peng, C. Chen, J. Chen, et al., Org. Lett. 16(2014) 3776-3779;
  (g) J. Chen, C. Chen, J. Chen, G. Wang, H. Qu, Chem. Commun. 51(2015) 1356-1359;
  (h) J. Sheng, Y. Wang, X. Su, R. He, C. Chen, Angew. Chem. Int. Ed 56(2017) 4824-4828.
9. [9]
  (a) E. Lindstedt, E. Stridfeldt, B. Olofsson, Org. Lett. 18(2016) 4234-4237;
  (b) E. Lindstedt, R. Ghosh, B. Olofsson, Org. Lett. 15(2013) 6070-6073;
  (c) N. Jalalian, E. E. Ishikawa, J. L. F. Silva, B. Olofsson, Org. Lett. 13(2011) 1552-1555.
10. [10]
  (a) S. H. Han, S. Kim, U. De, et al., J. Org. Chem. 81(2016) 12416-12425;
  (b) C. A. Menendez, F. Nador, G. Radivoy, D. C. Gerbino, Org. Lett. 16(2014) 2846-2849;
  (c) T. Stopka, L. Marzo, M. Zurro, et al., Angew. Chem. Int. 54(2015) 5049-5053;
  (d) J. Tang, S. Zhao, Y. Wei, Z. Quan, C. Huo, Org. Biomol. Chem. 15(2017) 1589-1592.
11. [11]
  (a) J. Zhao, D. Yue, M. A. Campo, R. C. Larock, J. Am. Chem. Soc. 129(2007) 5288-5295;
  (b) H. R. Zhang, P. Shi, C. Gan, A. Liu, Q. Ding, A. Wang, K. Lei, Angew. Chem. Int. Ed. 51(2012) 5204-5207.
12. [12]
  Okuma, A. Nojima, N. Matsunaga, K. Shioji, Org Lett. 11(2009) 169-171. doi: 10.1021/ol802597x
1. [1]
  Ying Xu , Chengying Shen , Hailong Yuan , Wei Wu . Mapping multiple phases in curcumin binary solid dispersions by fluorescence contrasting. Chinese Chemical Letters, 2024, 35(9): 109324-. doi: 10.1016/j.cclet.2023.109324
2. [2]
  Ruilong Geng , Lingzi Peng , Chang Guo . Dynamic kinetic stereodivergent transformations of propargylic ammonium salts via dual nickel and copper catalysis. Chinese Chemical Letters, 2024, 35(8): 109433-. doi: 10.1016/j.cclet.2023.109433
3. [3]
  Rong-Nan Yi , Wei-Min He . Electron donor-acceptor complex enabled arylation of dithiocarbamate anions with thianthrenium salts under aqueous micellar conditions. Chinese Chemical Letters, 2024, 35(11): 110194-. doi: 10.1016/j.cclet.2024.110194
4. [4]
  Junxin Li , Chao Chen , Yuzhen Dong , Jian Lv , Jun-Mei Peng , Yuan-Ye Jiang , Daoshan Yang . Ligand-promoted reductive coupling between aryl iodides and cyclic sulfonium salts by nickel catalysis. Chinese Chemical Letters, 2024, 35(11): 109732-. doi: 10.1016/j.cclet.2024.109732
5. [5]
  Xianping Du , Ying Huang , Chen Chen , Zhenhe Feng , Meng Zong . Encapsulating Si particles in multiple carbon shells with pore-rich for constructing free-standing anodes of lithium storage. Chinese Chemical Letters, 2024, 35(12): 109990-. doi: 10.1016/j.cclet.2024.109990
6. [6]
  Tong Su , Yue Wang , Qizhen Zhu , Mengyao Xu , Ning Qiao , Bin Xu . Multiple conductive network for KTi₂(PO₄)₃ anode based on MXene as a binder for high-performance potassium storage. Chinese Chemical Letters, 2024, 35(8): 109191-. doi: 10.1016/j.cclet.2023.109191
7. [7]
  Yi Cao , Xiaojiao Ge , Yuanyuan Wei , Lulu He , Aiguo Wu , Juan Li . Tumor microenvironment-activatable neuropeptide-drug conjugates enhanced tumor penetration and inhibition via multiple delivery pathways and calcium deposition. Chinese Chemical Letters, 2024, 35(4): 108672-. doi: 10.1016/j.cclet.2023.108672
8. [8]
  Xin Jiang , Han Jiang , Yimin Tang , Huizhu Zhang , Libin Yang , Xiuwen Wang , Bing Zhao . g-C₃N₄/TiO_2-X heterojunction with high-efficiency carrier separation and multiple charge transfer paths for ultrasensitive SERS sensing. Chinese Chemical Letters, 2024, 35(10): 109415-. doi: 10.1016/j.cclet.2023.109415
9. [9]
  Liangfeng Yang , Liang Zeng , Yanping Zhu , Qiuan Wang , Jinheng Li . Copper-catalyzed photoredox 1,4-amidocyanation of 1,3-enynes with N-amidopyridin-1-ium salts and TMSCN: Facile access to α-amido allenyl nitriles. Chinese Chemical Letters, 2024, 35(11): 109685-. doi: 10.1016/j.cclet.2024.109685
10. [10]
  Peiyan Zhu , Yanyan Yang , Hui Li , Jinhua Wang , Shiqing Li . Rh(Ⅲ)‐Catalyzed sequential ring‐retentive/‐opening [4 + 2] annulations of 2H‐imidazoles towards full‐color emissive imidazo[5,1‐a]isoquinolinium salts and AIE‐active non‐symmetric 1,1′‐biisoquinolines. Chinese Chemical Letters, 2024, 35(10): 109533-. doi: 10.1016/j.cclet.2024.109533