Citation: Sun Mingna, Zhou Yi, Zhang Peiquan, Sun Mingjiao, Tao Yiwen. "One Pot" Synthesis of 3-Amino-5, 7-dihydroxy-4-methyl Coumarin via Pechmann Reaction Catalyzed by BF₃·Et₂O[J]. Chemistry, ;2019, 82(6): 559-562. shu

"One Pot" Synthesis of 3-Amino-5, 7-dihydroxy-4-methyl Coumarin via Pechmann Reaction Catalyzed by BF₃·Et₂O

1.
Key Laboratory of Molecular and Clinical Pharmacology, School of Pharmaceutical Sciences & The Fifth Affiliated Hospital, Guangzhou Medical University, Gugangzhou 511436
2.
Institute of Cancer, Hangzhou Cancer Hospital, Hangzhou 310002

Corresponding author: Tao Yiwen, yywentao@aliyun.com
Received Date: 27 December 2018
Accepted Date: 18 February 2019

Figures(3)

3-Amino-5, 7-dihydroxy-4-methyl coumarin (4) is a new important organic intermediate, which can be used to synthesize various bioactive agents. In this work, compound 4 was synthesized in one pot from phloroglucinol and ethyl 2-acetylamino acetoacetate (2), which was prepared from ethyl acetoacetate by oxime formation, reduction and acylation successively, by Pechmann condensation and deacetylation in series under the catalysis of BF₃·Et₂O. All intermediates and the final product were confirmed by ¹H NMR、¹³C NMR and MS. This method has considerable advantages in terms of the use of easily available raw material, less steps, simple operation, mild reaction conditions and high yield.
- 3-Amino-5, 7-dihydroxy-4-methylcoumarin,
- BF₃·Et₂O,
- Pechmann reaction,
- Synthesis
1. [1]
2. [2]
  K Shylaja, V Srinivas, V Ravinder. World J. Pharm. Sci., 2016, 4(3): 375~383.
3. [3]
  A A H Kadhum, A B Mohamad, A A Al-Amiery et al. Molecules, 2011, 16(8): 6969~6984.
4. [4]
  B S Shyamala, V J Tyagaraju, P V Ananthalakshmi et al. Acta Cienc. Indica Chem., 2010, 36(3): 225~230.
5. [5]
  R Sharma, S S Soman. Pharmanest, 2015, 6(1): 2679~2684.
6. [6]
  M J Matos, S Vilar, S Kachler et al. Bioorg. Chem., 2015, 61: 1~6.
7. [7]
  H Matla, R S Bhosale, S Polepalli et al. Chem. Bio. Interf., 2015, 5(1): 34~43.
8. [8]
  V Maddi, S N Mamledesai, D Satyanarayana et al. Indian J. Pharm. Sci., 2007, 69(6): 847~849.
9. [9]
  M Cussac. FR: 2699175 A1, 1994.
10. [10]
  S Sen, V Srivastava. J. Indian Chem. Soc., 1989, 66(3): 166~168.
11. [11]
  S L Guo, G Liu, C B Fan. RSC Adv., 2018, 8(40): 22786~22798.
12. [12]
13. [13]
14. [14]
  J E T Corrie. J. Chem. Soc. Perkin Transac., 1990, (7): 2151~2152.
15. [15]
16. [16]
17. [17]
18. [18]
19. [19]
  M N Sun, J F Hu, X Y Song et al. Eur. J. Med. Chem., 2013, 67: 39~53.
20. [20]
  G Li, D M Wang, M N Sun et al. J. Med. Chem., 2010, 53(4): 1741~1754.
21. [21]
  A Homer, R E Wilkins. J. Am. Chem. Soc., 1938, 60(6): 1328~1331.
22. [22]
  N F Albertson, B F Tullar, J A King et al. J. Am. Chem. Soc., 1948, 70(3): 1150~1153.
1. [1]
  Lifang HE , Wenjie TANG , Yaoze LUO , Mingsheng LIANG , Jianxin TANG , Yuxuan WU , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two dialkyltin complexes constructed based on 2, 2′-bipyridin-6, 6′-dicarboxylic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1601-1609. doi: 10.11862/CJIC.20250012
2. [2]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
3. [3]
  Xinyi Zhang , Kai Ren , Yanning Liu , Zhenyi Gu , Zhixiong Huang , Shuohang Zheng , Xiaotong Wang , Jinzhi Guo , Igor V. Zatovsky , Junming Cao , Xinglong Wu . Progress on Entropy Production Engineering for Electrochemical Catalysis. Acta Physico-Chimica Sinica, 2024, 40(7): 2307057-0. doi: 10.3866/PKU.WHXB202307057
4. [4]
  Chunling Qin , Shuang Chen , Hassanien Gomaa , Mohamed A. Shenashen , Sherif A. El-Safty , Qian Liu , Cuihua An , Xijun Liu , Qibo Deng , Ning Hu . Regulating HER and OER Performances of 2D Materials by the External Physical Fields. Acta Physico-Chimica Sinica, 2024, 40(9): 2307059-0. doi: 10.3866/PKU.WHXB202307059
5. [5]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
6. [6]
  Bin SUN , Heyan JIANG . Glucose-modified bis-Schiff bases: Synthesis and bio-activities in Alzheimer′s disease therapy. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1338-1350. doi: 10.11862/CJIC.20240428
7. [7]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
8. [8]
  Lei Feng , Ze-Min Zhu , Ying Yang , Zongbin He , Jiafeng Zou , Man-Bo Li , Yan Zhao , Zhikun Wu . Long-Pursued Structure of Au₂₃(S-Adm)₁₆ and the Unexpected Doping Effects. Acta Physico-Chimica Sinica, 2024, 40(5): 2305029-0. doi: 10.3866/PKU.WHXB202305029
9. [9]
  Liping GUO . Synthesis and crystal structure characterization of yttrium imido complex: The reactivity of 2-substituted-1-amino-o-carborane with yttrium dialkyl complex. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1409-1415. doi: 10.11862/CJIC.20250065
10. [10]
  Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
11. [11]
  Peng Wang , Jianjun Wang , Ni Song , Xin Zhou , Ming Li . Radical dehydroxymethylative fluorination of aliphatic primary alcohols and diverse functionalization of α-fluoroimides via BF₃·OEt₂-catalyzed C‒F bond activation. Chinese Chemical Letters, 2025, 36(1): 109748-. doi: 10.1016/j.cclet.2024.109748
12. [12]
  Guoqiang Chen , Zixuan Zheng , Wei Zhong , Guohong Wang , Xinhe Wu . Molten Intermediate Transportation-Oriented Synthesis of Amino-Rich g-C₃N₄ Nanosheets for Efficient Photocatalytic H₂O₂ Production. Acta Physico-Chimica Sinica, 2024, 40(11): 2406021-0. doi: 10.3866/PKU.WHXB202406021
13. [13]
  Yongqing Kuang , Jie Liu , Jianjun Feng , Wen Yang , Shuanglian Cai , Ling Shi . Experimental Design for the Two-Step Synthesis of Paracetamol from 4-Hydroxyacetophenone. University Chemistry, 2024, 39(8): 331-337. doi: 10.12461/PKU.DXHX202403012
14. [14]
  Yanglin Jiang , Mingqing Chen , Min Liang , Yige Yao , Yan Zhang , Peng Wang , Jianping Zhang . Experimental and Theoretical Investigations of Solvent Polarity Effect on ESIPT Mechanism in 4′-N,N-diethylamino-3-hydroxybenzoflavone. Acta Physico-Chimica Sinica, 2025, 41(2): 2309027-0. doi: 10.3866/PKU.WHXB202309027
15. [15]
  Xiaoyang Li , Xiaowei Huang , Yimeng Zhang , Huan Liu , Shao Jin , Junpeng Zhuang . Comprehensive Chemical Experiments on the Synthesis of 1,3-Dibromo-5,5-Dimethylhydantoin and Its Application as a Brominating Reagent. University Chemistry, 2025, 40(7): 286-293. doi: 10.12461/PKU.DXHX202408035
16. [16]
  Wei Zhong , Dan Zheng , Yuanxin Ou , Aiyun Meng , Yaorong Su . Simultaneously Improving Inter-Plane Crystallization and Incorporating K Atoms in g-C₃N₄ Photocatalyst for Highly-Efficient H₂O₂ Photosynthesis. Acta Physico-Chimica Sinica, 2024, 40(11): 2406005-0. doi: 10.3866/PKU.WHXB202406005
17. [17]
  Yajin Li , Huimin Liu , Lan Ma , Jiaxiong Liu , Dehua He . Photothermal Synthesis of Glycerol Carbonate via Glycerol Carbonylation with CO₂ over Au/Co₃O₄-ZnO Catalyst. Acta Physico-Chimica Sinica, 2024, 40(9): 2308005-0. doi: 10.3866/PKU.WHXB202308005
18. [18]
  Yahui HAN , Jinjin ZHAO , Ning REN , Jianjun ZHANG . Synthesis, crystal structure, thermal decomposition mechanism, and fluorescence properties of benzoic acid and 4-hydroxy-2, 2′: 6′, 2″-terpyridine lanthanide complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 969-982. doi: 10.11862/CJIC.20240395
19. [19]
  Yan Cheng , Hua-Peng Ruan , Yan Peng , Longhe Li , Zhenqiang Xie , Lang Liu , Shiyong Zhang , Hengyun Ye , Zhao-Bo Hu . Magnetic, dielectric and luminescence synergetic switchable effects in molecular material [Et₃NCH₂Cl]₂[MnBr₄]. Chinese Chemical Letters, 2024, 35(4): 108554-. doi: 10.1016/j.cclet.2023.108554
20. [20]
  Chao Liu , Huan Yu , Jiaming Li , Xi Yu , Zhuangzhi Yu , Yuxi Song , Feng Zhang , Qinfang Zhang , Zhigang Zou . 具有光热效应的多级Ti₃C₂/Bi₁₂O₁₇Br₂肖特基异质结简单合成及其太阳能驱动抗生素光降解的研究. Acta Physico-Chimica Sinica, 2025, 41(7): 100075-0. doi: 10.1016/j.actphy.2025.100075

Get Citation

PDF

XML

Metrics

PDF Downloads(6)
Abstract views(1437)
HTML views(201)

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

"One Pot" Synthesis of 3-Amino-5, 7-dihydroxy-4-methyl Coumarin via Pechmann Reaction Catalyzed by BF3·Et2O

Metrics

通讯作者: 陈斌, bchen63@163.com

"One Pot" Synthesis of 3-Amino-5, 7-dihydroxy-4-methyl Coumarin via Pechmann Reaction Catalyzed by BF₃·Et₂O