Citation: Guo Dongdong, Zhang Wuxia, Wang Yongqiang. Study on Synthetic Approach to 8-Hydroxyisocoumarin[J]. Chinese Journal of Organic Chemistry, ;2019, 39(9): 2650-2654. doi: 10.6023/cjoc201906001 shu

Study on Synthetic Approach to 8-Hydroxyisocoumarin

a.
College of Arts and Sciences, Shanxi Agricultural University, Taigu, Shanxi 030801
b.
Department of Chemistry & Materials Science, Northwest University, Xi'an 710069

Corresponding author: Wang Yongqiang, wangyq@nwu.edu.cn
Received Date: 3 June 2019
Revised Date: 22 July 2019
Available Online: 7 September 2019
Fund Project: the National Natural Science Foundation of China 31800678the Shanxi Excellent Doctor Grant Award SXYBKY201737Project supported by the National Natural Science Foundation of China (No. 31800678), the Shanxi Excellent Doctor Grant Award (No. SXYBKY201737) and the Science and Technology Innovation Project of Shanxi Agricultural University (No. 2017YJ38)the Science and Technology Innovation Project of Shanxi Agricultural University 2017YJ38

Figures(2)

A new method for the synthesis of 8-hydroxyisocoumarin is reported. 8-Hydroxyisocoumarin was synthesized from Meldrum's acid by Friedel-Crafts acylation, carbonyl protection, ester reduction and deprotection. The key intermediate 3-ethynyl-2-(hydroxymethyl)cyclohex-2-en-1-one was synthesized by acidic cycloaddition, aromatization of cyclohexanone ring and 2, 3-dicyano-5, 6-dichlorobenzoquinone (DDQ) oxidation. The structures were characterized by ¹H NMR, ¹³C NMR, IR, and HRMS.
- isocoumarin,
- 8-hydroxyisocoumarin,
- pyran,
- aromatization,
- synthetic method
1. [1]
  (a) Barry, R. D. Chem. Rev. 1964, 64, 229.
  (b) Hill, R. A. Fortschritte der Chemie Organischer Naturstoffe/Progress in the Chemistry of Organic Natural Products, Springer, Vienna, 1986, pp. 1~78.
2. [2]
  Fang, Z.-X.; Liu, J.-Y.; Qiao, Y.-H. Chin. J. Org. Chem. 2018, 38, 1985 (in Chinese).
3. [3]
  Dong, G.; Li, C.; Liu, H. Molecules 2019, 24, 937. doi: 10.3390/molecules24050937
4. [4]
  Neog, K.; Dutta, D.; Das, B.; Gogoi, P. Org. Lett. 2017, 19, 730. doi: 10.1021/acs.orglett.7b00027
5. [5]
  Pal, S.; Chatare, V.; Pal, M. Curr. Org. Chem. 2011, 15, 782. doi: 10.2174/138527211794518970
6. [6]
  Majetich, G.; Grove, J. L. Heterocycles 2012, 84, 983. doi: 10.3987/COM-11-S(P)73
7. [7]
  Narasimhan, N. S.; Mali, R. S. Synthesis 1983, 957.
8. [8]
  Napolitano, E. Org. Prep. Proced. Int. 1997, 29, 631. doi: 10.1080/00304949709355245
9. [9]
  Larock, R. C.; Doty, M. J.; Han, X. J. Org. Chem. 1999, 64, 8770. doi: 10.1021/jo9821628
10. [10]
  Larock, R. C.; Yum, E. K.; Doty, M. J.; Sham, K. K. C. J. Org. Chem. 1995, 60, 3270. doi: 10.1021/jo00116a003
11. [11]
  Larock, R. C.; Varaprath, S.; Lau, H. H.; Fellows, C. A. J. Am. Chem. Soc. 1984, 106, 5274. doi: 10.1021/ja00330a041
12. [12]
  Korte, D. E.; Hegedus, L. S.; Wirth, R. K. J. Org. Chem. 1977, 42, 1329. doi: 10.1021/jo00428a013
13. [13]
  Cherry, K.; Parrain, J. L.; Thibonnet, J.; Duchêne, A.; Abarbri, M. J. Org. Chem. 2005, 70, 6669. doi: 10.1021/jo050638z
14. [14]
  Subramanian, V.; Batchu, V. R.; Barange, D.; Pal, M. J. Org. Chem. 2005, 70, 4778. doi: 10.1021/jo050440e
15. [15]
  Roy, S.; Roy, S.; Neuenswander, B.; Hill, D.; Larock, R. C. J. Comb. Chem. 2009, 11, 1128. doi: 10.1021/cc9001197
16. [16]
  Nayyar, N. K.; Hutchison, D. R.; Martinelli, M. J. J. Org. Chem. 1997, 62, 982. doi: 10.1021/jo9614598
17. [17]
  Organ, M. G.; Wang, J. J. Org. Chem. 2002, 67, 7847. doi: 10.1021/jo0204707
18. [18]
  Davidson, D.; Bernhard, S. A. J. Am. Chem. Soc. 1948, 70, 3426. doi: 10.1021/ja01190a060
19. [19]
  Oikawa, Y.; Sugano, K.; Yonemitsu, O. J. Org. Chem. 1978, 43, 2087. doi: 10.1021/jo00404a066
20. [20]
  Srikrishna, A.; Ramachary, D. B. Tetrahedron Lett. 2002, 43, 2765. doi: 10.1016/S0040-4039(02)00381-7
21. [21]
  Yamazaki, T.; Kobayashi, R.; Kitazume, T.; Kubota, T. J. Org. Chem. 2006, 71, 2499. doi: 10.1021/jo052434o
22. [22]
  Meyer, W. L.; Brannon, M. J.; Burgos, C. G. J. Org. Chem. 1985, 50, 438. doi: 10.1021/jo00204a003
1. [1]
  Yunhao Zhang , Yinuo Wang , Siran Wang , Dazhen Xu . Progress in Selective Construction of Functional Aromatics from Nitrogenous Cycloalkanes. University Chemistry, 2024, 39(11): 136-145. doi: 10.3866/PKU.DXHX202401083
2. [2]
  Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050
3. [3]
  Zhenhua Wang , Haoyang Feng , Xiaoyang Shao , Wenru Fan . Vitamins in Solid Propellants: Controlled Synthesis of Neutral Macromolecular Bonding Agents. University Chemistry, 2025, 40(4): 1-9. doi: 10.3866/PKU.DXHX202401007
4. [4]
  Yixuan Zhu , Qingtong Wang , Jin Li , Lin Chen , Junlong Zhao . Blog of Oxytocin. University Chemistry, 2024, 39(9): 134-140. doi: 10.12461/PKU.DXHX202310090
5. [5]
  Rui Gao , Ying Zhou , Yifan Hu , Siyuan Chen , Shouhong Xu , Qianfu Luo , Wenqing Zhang . Design, Synthesis and Performance Experiment of Novel Photoswitchable Hybrid Tetraarylethenes. University Chemistry, 2024, 39(5): 125-133. doi: 10.3866/PKU.DXHX202310050
6. [6]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
7. [7]
  Yukun Xing , Xiaoyu Xie , Fangfang Chen . A Sunlit Gift: Vitamin D. University Chemistry, 2024, 39(9): 28-34. doi: 10.12461/PKU.DXHX202402006
8. [8]
  Jijun Sun , Qianlang Wang , Qian Chen , Quanqin Zhao , Shumei Zhai . The Antibiotic Legion’s Manifesto to Human Allies. University Chemistry, 2025, 40(4): 307-321. doi: 10.12461/PKU.DXHX202405206
9. [9]
  Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
10. [10]
  Yaling Chen . Basic Theory and Competitive Exam Analysis of Dynamic Isotope Effect. University Chemistry, 2024, 39(8): 403-410. doi: 10.3866/PKU.DXHX202311093
11. [11]
  Xiaoning TANG , Junnan LIU , Xingfu YANG , Jie LEI , Qiuyang LUO , Shu XIA , An XUE . Effect of sodium alginate-sodium carboxymethylcellulose gel layer on the stability of Zn anodes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1452-1460. doi: 10.11862/CJIC.20240191
12. [12]
  Jianjun LI , Mingjie REN , Lili ZHANG , Lingling ZENG , Huiling WANG , Xiangwu MENG . UV-assisted degradation of tetracycline hydrochloride by MnFe₂O₄@activated carbon activated persulfate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1869-1880. doi: 10.11862/CJIC.20240187
13. [13]
  Shijie Li , Ke Rong , Xiaoqin Wang , Chuqi Shen , Fang Yang , Qinghong Zhang . Design of Carbon Quantum Dots/CdS/Ta₃N₅ S-Scheme Heterojunction Nanofibers for Efficient Photocatalytic Antibiotic Removal. Acta Physico-Chimica Sinica, 2024, 40(12): 2403005-. doi: 10.3866/PKU.WHXB202403005
14. [14]
  Wanqun Hu , Pingping Zhu , Yuan Zheng , Wanqun Zhang , Wei Shao , Hong Wu , Qiang Zhou , Kaiping Yang , Xiang Sheng . Design and Practice of Ideological and Political Case Study in Instrumental Analysis Experiment Course: the Extraction and Structural Identification of Artemisinin. University Chemistry, 2024, 39(2): 203-207. doi: 10.3866/PKU.DXHX202310062
15. [15]
  Shui Hu , Houjin Li , Zhenming Zang , Lianyun Li , Rong Lai . Integration of Science and Education Promotes the Construction of Undergraduate-to-Master’s Integration Experimental Courses: A Case Study on the Extraction, Separation and Identification of Artemisinin from Artemisia annua. University Chemistry, 2024, 39(4): 314-321. doi: 10.3866/PKU.DXHX202310063
16. [16]
  Junjie Zhang , Yue Wang , Qiuhan Wu , Ruquan Shen , Han Liu , Xinhua Duan . Preparation and Selective Separation of Lightweight Magnetic Molecularly Imprinted Polymers for Trace Tetracycline Detection in Milk. University Chemistry, 2024, 39(5): 251-257. doi: 10.3866/PKU.DXHX202311084
17. [17]
  Liwei Wang , Guangran Ma , Li Wang , Fugang Xu . A Comprehensive Analytical Chemistry Experiment: Colorimetric Detection of Vitamin C Using Nanozyme and Smartphone. University Chemistry, 2024, 39(8): 255-262. doi: 10.3866/PKU.DXHX202312094
18. [18]
  Jinwang Wu , Qijing Xie , Chengliang Zhang , Haifeng Shi . 自旋极化增强ZnFe_1.2Co_0.8O₄/BiVO₄ S型异质结光催化性能降解四环素. Acta Physico-Chimica Sinica, 2025, 41(5): 100050-. doi: 10.1016/j.actphy.2025.100050
19. [19]
  Zongyuan Chen , ChunSheng Shi , Yiwen Li , Ganlin Zu , Qiang Jin , Haishan Wang , Fujun Wang , Dekun Yan , Zhijun Guo , Wangsuo Wu . Measurement of Uranium Isotopes in Environmental Water Samples by Alpha-Spectroscopy: Design of an Undergraduate Radiochemistry Experiment. University Chemistry, 2025, 40(4): 353-358. doi: 10.12461/PKU.DXHX202406103
20. [20]
  Wenjie SHI , Fan LU , Mengwei CHEN , Jin WANG , Yingfeng HAN . Synthesis and host-guest properties of imidazolium-functionalized zirconium metal-organic cage. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 105-113. doi: 10.11862/CJIC.20240360

Get Citation

PDF

XML

Metrics

PDF Downloads(8)
Abstract views(1495)
HTML views(310)

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