Citation: Li Zhijuan, Wang Weihua, Jian Hui, Li Wenjuan, Dai Bin, He Lin. Synthesis of 9-phenol-substituted xanthenes by cascade O-insertion/1, 6-conjugate addition of benzyne with ortho-hydroxyphenyl substituted para-quinone methides[J]. Chinese Chemical Letters, ;2019, 30(2): 386-388. doi: 10.1016/j.cclet.2018.04.003 shu

Synthesis of 9-phenol-substituted xanthenes by cascade O-insertion/1, 6-conjugate addition of benzyne with ortho-hydroxyphenyl substituted para-quinone methides

Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, School of Chemistry and Chemical Engineering, Shihezi University, Shihezi 832000, China

helin@shzu.edu.cn

Received Date: 29 January 2018
Revised Date: 21 March 2018
Accepted Date: 2 April 2018
Available Online: 7 February 2018

Figures(2)

The cascade O-insertion/1, 6 conjugate addition between benzynes and ortho-hydroxyphenyl substituted para-quinone methides has been reported, affording 9-phenol substituted xanthenes in 49%-84% yields.
- Benzyne,
- para-Quinone methides,
- Xanthene,
- Cascade reaction,
- Cycloaddition
1. [1]
  (a) N. Sato, M. Jitsuoka, T. Shibata, et al., J. Med. Chem. 51 (2008) 4765-4770;
  (b) L. Äjemyr, T. Sandén, J. Widengren, P. Brzezinski, Biochemistry 48 (2009) 2173-2179;
  (c) M.C. de la Fuente, D. Dominguez, J. Org. Chem. 72 (2007) 8804-8810;
  (d) T. Kobayashi, Y. Urano, M. Kamiya, J. Am. Chem. Soc.129 (2007) 6696-6697.
2. [2]
  N. Fitchen, P. O'Shea, P. Williams, K.R. Hardie, Mol. Immunol. 40(2003) 407-411. doi: 10.1016/S0161-5890(03)00153-6
3. [3]
  (a) Y. Nagano, J. Am. Chem. Soc. 129 (2007) 10324-10325;
  (b) M.P. Okoh, J.L. Hunter, J.E.T. Corrie, M.R. Webb, Biochemistry 45 (2006) 14764-14771;
  (c) L. Äjemyr, T. Sanden, J. Widengren, P. Brzezinski, Biochemistry 48 (2009) 2173-2179.
4. [4]
  T. Lazarides, T. McCormick, P. Du, et al., J. Am. Chem. Soc. 131(2009) 9192-9194. doi: 10.1021/ja903044n
5. [5]
  (a) S. Bhojgude, A. Bhunia, A.T. Biju, Acc. Chem. Res. 49 (2016) 1658-1670;
  (b) A. Bhunia, S.R. Yetra, A.T. Biju, Chem. Soc. Rev. 41 (2012) 3140-3152;
  (c) S. Bhojgude, A.T. Biju, Angew. Chem. Int. Ed. 51 (2012) 1520-1522;
  (d) P.M. Tadross, B.M. Stoltz, Chem. Rev. 112 (2012) 3550-3577;
  (e) A.V. Dubrovskiy, N.A. Markina, R.C. Larock, Org. Biomol. Chem. 11 (2013) 191-218;
  (f) C. Wu, F. Shi, Asian J. Org. Chem. 2 (2013) 116-125.
6. [6]
  K. Okuma, A. Nojima, N. Matsunaga, K. Shioji, Org. Lett. 11(2009) 169-171. doi: 10.1021/ol802597x
7. [7]
  (a) J. Zhao, R.C. Larock, Org. Lett. 7 (2005) 4273-4275;
  (b) J. Zhao, R.C. Larock, J. Org. Chem. 72 (2007) 583-588;
  (c) C. Lu, A.V. Dubrovskiy, R.C. Larock, Tetrahedron Lett. 53 (2012) 2202-2205;
  (d) A.V. Dubrovskiy, R.C. Larock, Org. Lett. 12 (2010) 1180-1183;
  (e) Y. Fang, D.C. Rogness, R.C. Larock, F. Shi, J. Org. Chem. 77 (2012) 6262-6270.
8. [8]
  X. Huang, T. Zhang, J. Org. Chem. 75(2010) 506-509. doi: 10.1021/jo902311a
9. [9]
  (a) P. Chauhan, U. Kaya, D. Enders, Adv. Synth. Catal. 359 (2017) 888-912;
  (b) M.M. Toteva, J.P. Richard, Adv. Phys. Org. Chem. 45 (2011) 39-91;
  (c) A. Parra, M. Tortosa, ChemCatChem 7 (2015) 1524-1526.
10. [10]
  (a) Z. Yuan, K. Gai, Y. Wu, et al., Chem. Commun. 53 (2017) 3485-3488;
  (b) Z. Yuan, L. Liu, R. Pan, H. Yao, A. Lin, J. Org. Chem. 82 (2017) 8743-8751;
  (c) Z. Yuan, R. Pan, H. Zhang, et al., Adv. Synth. Catal. 359 (2017) 4244-4249;
  (d) V. Reddy, R.V. Anand, Org. Lett. 17 (2015) 3390-3393;
  (e) P. Goswami, G. Singh, R.V. Anand, Org. Lett. 19 (2017) 1982-1985;
  (f) K. Zhao, Y. Zhi, A. Wang, D. Enders, ACS Catal. 6 (2016) 657-660;
  (g) Y. Lou, P. Cao, T. Jia, et al., Angew. Chem. Int. Ed. 54 (2015) 12134-12138;
  (h) W.D. Chu, L.F. Zhang, X. Bao, et al., Angew. Chem. Int. Ed. 52 (2013) 9229-9233;
  (i) X.Z. Zhang, Y.H. Deng, K.J. Gan, et al., Org. Lett. 19 (2017) 1752-1755;
  (j) Z. Wang, Y.F. Wong, J. Sun, Angew. Chem. Int. Ed. 54 (2015) 13711-13714;
  (k) Y.F. Wong, Z. Wang, J. Sun, Org. Biomol. Chem. 14 (2016) 5751-5754;
  (l) H. Lv, W. Jia, L. Sun, S. Ye, Angew. Chem. Int. Ed. 52 (2013) 8607-8610;
  (m) H. Lv, L. You, S. Ye, Adv. Synth. Catal. 351 (2009) 2822-2826;
  (n) J.J. Zhao, S.B. Sun, S.H. He, Q. Wu, F. Shi, Angew. Chem. Int. Ed. 54 (2015) 5460-5464;
  (o) J.J. Zhao, Y.C. Zhang, M.M. Xu, M. Tang, F. Shi, J. Org. Chem. 80 (2015) 10016-10024;
  (p) Y.C. Zhang, Q.N. Zhu, X. Yang, L.J. Zhou, F. Shi, J. Org. Chem. 81 (2016) 1681-1688;
  (q) P. Chen, K. Wang, W.G. Guo, et al., Angew. Chem. Int. Ed. 56 (2017) 3689-3693;
  (r) Z.B. Wang, J.W. Sun, Org. Lett. 19 (2017) 2334-2337.
11. [11]
  (a) K. Zhao, Y. Zhi, T. Shu, et al., Angew. Chem. Int. Ed. 55 (2016) 12104-12108;
  (b) S. Liu, X.C. Lan, K. Chen, et al., Org. Lett. 19 (2017) 3831-3834;
  (c) J.Y. Liao, Q. Ni, Y. Zhao, Org. Lett. 19 (2017) 4074-4077;
  (d) L. Liu, Z. Yuan, R. Pan, et al., Org. Chem. Front. 5 (2018) 623-628.
12. [12]
  (a) L. He, J.X. Pian, J.F. Shi, G.F. Du, B. Dai, Tetrahedron 70 (2014) 2400-2405;
  (b) J.X. Pian, L. He, G.F. Du, H. Guo, B. Dai, J. Org. Chem. 79 (2014) 5820-5826;
  (c) K. Liu, L.L. Liu, C.Z. Gu, B. Dai, L. He, RSC Adv. 6 (2016) 33606-33610;
  (d) L.L. Liu, Z.J. Li, C.Z. Gu, L. He, B. Dai, J. Saudi, Chem. Soc. 21 (2017) 458-465;
  (e) L. He, J.X. Pian, J.Y.Z. Zhang Li, Chin. Chem. Lett. 23 (2012) 1359-1362;
  (f) J. Zhang, K. Liu, H. Jian, Z.J. Li, L. He, Tetrahedron Lett. 58 (2017) 2964-2968;
  (g) H. Jian, K. Liu, W.H. Wang, et al., Tetrahedron Lett. 58 (2017) 1137-1141.
13. [13]
  G.J. Mei, S.L. Xu, W.Q. Zheng, C.Y. Bian, F. Shi, J. Org. Chem. 83(2018) 1414-1421. doi: 10.1021/acs.joc.7b02942
14. [14]
  Y. Himeshima, T. Sonoda, H. Kobayashi, Chem. Lett. 12(1983) 1211-1214. doi: 10.1246/cl.1983.1211
1. [1]
  Qian Liu , Yi Shi , Kaiya Wang , Xiao-Yu Hu . Tailoring cascade hydrolysis and cyclization efficiency in confined spaces via spatial and electrostatic regulation. Chinese Chemical Letters, 2025, 36(12): 111462-. doi: 10.1016/j.cclet.2025.111462
2. [2]
  Xiaohui Fu , Yanping Zhang , Juan Liao , Zhen-Hua Wang , Yong You , Jian-Qiang Zhao , Mingqiang Zhou , Wei-Cheng Yuan . Palladium-catalyzed enantioselective decarboxylation of vinyl cyclic carbamates: Generation of amide-based aza-1,3-dipoles and application to asymmetric 1,3-dipolar cycloaddition. Chinese Chemical Letters, 2024, 35(12): 109688-. doi: 10.1016/j.cclet.2024.109688
3. [3]
  Jun Liu , Zhaoyu Feng , Renming Pan , Xiaolong Yu , Meijuan Zhou , Gang Zhao , Hongyu Wang . Enantioselective regulation to coronal polyheterocyclic compounds via phosphonium salt-catalyzed cycloadditions of azomethine imines with γ-butenolides. Chinese Chemical Letters, 2025, 36(8): 110647-. doi: 10.1016/j.cclet.2024.110647
4. [4]
  Gangsheng Li , Xiang Yuan , Fu Liu , Zhihua Liu , Xujie Wang , Yuanyuan Liu , Yanmin Chen , Tingting Wang , Yanan Yang , Peicheng Zhang . Three-step synthesis of flavanostilbenes with a 2-cyclohepten-1-one core by Cu-mediated [5 + 2] cycloaddition/decarboxylation cascade. Chinese Chemical Letters, 2025, 36(2): 109880-. doi: 10.1016/j.cclet.2024.109880
5. [5]
  Ruolin CHENG , Yue WANG , Fei YANG , Huagen LIANG , Shijian LU . Application of metal-organic frameworks (MOFs) in photocatalytic CO₂ cycloaddition reaction: A mini review. Chinese Journal of Inorganic Chemistry, 2025, 41(12): 2429-2440. doi: 10.11862/CJIC.20250242
6. [6]
  Weichen WANG , Chunhua GONG , Junyong ZHANG , Yanfeng BI , Hao XU , Jingli XIE . Construction of two metal-organic frameworks by rigid bis(triazole) and carboxylate mixed-ligands and their catalytic properties for CO₂ cycloaddition reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1377-1386. doi: 10.11862/CJIC.20230415
7. [7]
  Yan-Li Li , Zhi-Ming Li , Kai-Kai Wang , Xiao-Long He . Beyond 1,4-addition of in-situ generated (aza-)quinone methides and indole imine methides. Chinese Chemical Letters, 2024, 35(7): 109322-. doi: 10.1016/j.cclet.2023.109322
8. [8]
  Kebo Xie , Qian Zhang , Fei Ye , Jungui Dai . A multi-enzymatic cascade reaction for the synthesis of bioactive C-oligosaccharides. Chinese Chemical Letters, 2024, 35(6): 109028-. doi: 10.1016/j.cclet.2023.109028
9. [9]
  Yue Sun , Yingnan Zhu , Jiahang Si , Ruikang Zhang , Yalan Ji , Jinjie Fan , Yuze Dong . Glucose-activated nanozyme hydrogels for microenvironment modulation via cascade reaction in diabetic wound. Chinese Chemical Letters, 2025, 36(4): 110012-. doi: 10.1016/j.cclet.2024.110012
10. [10]
  Min Yan , Zihao Ye , Ping Lu . Catalyst-free, visible-light-induced [2π + 2σ] cycloaddition towards azabicyclohexanes. Chinese Chemical Letters, 2025, 36(6): 110540-. doi: 10.1016/j.cclet.2024.110540
11. [11]
  Meixin Wang , Yizhi Zhang , Shanshan Liu , Xiao Shen . Synthesis of rigidified cyclohexanes enabled by visible-light-induced trifluoroacetylsilane-mediated [2 + 2] cycloaddition of cyclopropenes. Chinese Chemical Letters, 2025, 36(8): 110758-. doi: 10.1016/j.cclet.2024.110758
12. [12]
  Ruowen Liang , Chao Zhang , Guiyang Yan . Enhancing CO2 cycloaddition through ligand functionalization: A case study of UiO-66 metal-organic frameworks. Chinese Journal of Structural Chemistry, 2024, 43(2): 100211-100211. doi: 10.1016/j.cjsc.2023.100211
13. [13]
  Liliang Chu , Xiaoyan Zhang , Jianing Li , Xuelei Deng , Miao Wu , Ya Cheng , Weiping Zhu , Xuhong Qian , Yunpeng Bai . Continuous-flow synthesis of polysubstituted γ-butyrolactones via enzymatic cascade catalysis. Chinese Chemical Letters, 2024, 35(4): 108896-. doi: 10.1016/j.cclet.2023.108896
14. [14]
  Ji-Jia Zhou , Li-Gao Liu , Zhen-Tao Zhang , Hao-Xuan Dong , Xin Lu , Zhou Xu , Xin-Qi Zhu , Bo Zhou , Long-Wu Ye . Copper-catalyzed asymmetric cascade diyne cyclization/Meinwald rearrangement. Chinese Chemical Letters, 2025, 36(9): 110870-. doi: 10.1016/j.cclet.2025.110870
15. [15]
  Jing-Qi Tao , Shuai Liu , Tian-Yu Zhang , Hong Xin , Xu Yang , Xin-Hua Duan , Li-Na Guo . Photoinduced copper-catalyzed alkoxyl radical-triggered ring-expansion/aminocarbonylation cascade. Chinese Chemical Letters, 2024, 35(6): 109263-. doi: 10.1016/j.cclet.2023.109263
16. [16]
  Zhendong Liu , Sainan Liu , Bin Liu , Qi Meng , Meng Yuan , Chunzheng Yang , Yulong Bian , Ping'an Ma , Jun Lin . Fe(Ⅲ)-juglone nanoscale coordination polymers for cascade chemodynamic therapy through synergistic ferroptosis and apoptosis strategy. Chinese Chemical Letters, 2024, 35(11): 109626-. doi: 10.1016/j.cclet.2024.109626
17. [17]
  Yingtao Zhong , Ziwen Qiu , Yanmei Li , Jiaqi Huang , Zhenming Lu , Renjiang Kong , Ni Yan , Hong Cheng . Nutrients deprivation of biomimetic nanozymes for cascade catalysis triggered and oxidative damage induced tumor eradication. Chinese Chemical Letters, 2025, 36(3): 109846-. doi: 10.1016/j.cclet.2024.109846
18. [18]
  Bo Liu , Shuaiqiang Shao , Junjie Cai , Zijian Zhang , Feng Tian , Kun Yang , Fan Li . Signal cascade amplification of streptavidin-biotin-modified immunofluorescence nanocapsules for ultrasensitive detection of glial fibrillary acidic protein. Chinese Chemical Letters, 2025, 36(3): 109814-. doi: 10.1016/j.cclet.2024.109814
19. [19]
  Xueying Shi , Xiaoxuan Zhou , Bing Xiao , Hongxia Xu , Wei Zhang , Hongjie Hu , Shiqun Shao , Zhuxian Zhou , Youqing Shen , Xiaodan Xu , Jianbin Tang . A β-lapachone-loaded iron-polyphenol nanocomplex enhances chemodynamic therapy through cascade amplification of ROS in tumor. Chinese Chemical Letters, 2025, 36(5): 110178-. doi: 10.1016/j.cclet.2024.110178
20. [20]
  Chonglong He , Yulong Wang , Quan-Xin Li , Zichen Yan , Keyuan Zhang , Shao-Fei Ni , Xin-Hua Duan , Le Liu . Alkylarylation of alkenes with arylsulfonylacetate as bifunctional reagent via photoredox radical addition/Smiles rearrangement cascade. Chinese Chemical Letters, 2025, 36(5): 110253-. doi: 10.1016/j.cclet.2024.110253

Get Citation

PDF

XML

Metrics

PDF Downloads(5)
Abstract views(1301)
HTML views(40)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142