Citation: Zhongkui Zhao, Renzhi Li, Yu Li, Guiru Wang. Simple primary amine catalyzed aerobic reductive ring-cleavage of isoxazole motif[J]. Chinese Journal of Catalysis, ;2015, 36(2): 204-208. doi: 10.1016/S1872-2067(14)60200-X shu

Simple primary amine catalyzed aerobic reductive ring-cleavage of isoxazole motif

1.
State Key Laboratory of Fine Chemicals, Department of Catalysis Chemistry and Engineering, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, Liaoning, China

Corresponding author: Zhongkui Zhao,
Received Date: 25 June 2014
Available Online: 18 July 2014
Fund Project: 教育部新世纪优秀人才支持计划(NCET-12-0079) (NCET-12-0079) 中央高校基本科研业务费专项资金(DUT12LK51). (DUT12LK51)

A clean and highly efficient catalytic aerobic reductive ring-cleavage of 3-methylanthra[1,2-c]isoxazole-6,11-dione to 1-amino-2-acetylanthraquinone was performed using simple organic amines as organocatalysts and water as a green reaction medium. This method provides a new clean transformation of isoxazole-containing compounds to the corresponding ortho-amino ketones. The catalytic performance of various organic amines was carefully screened, and simple organic primary amines were found to be promising practical catalysts with outstanding catalytic performance. Isopropylamine as the organocatalyst gave 97.2% conversion of 3-methylanthra[1,2-c]isoxazole-6,11-dione, with 97.2% selectivity to 1-amino-2-acetylanthraquinone, in the presence of oxygen only, using 1 equiv. of hydrazine hydrate at room temperature for 3 h. A possible mechanism is also proposed.
- Organocatalysis,
- Simple primary amine,
- Aerobic reductive ring cleavage,
- 1-Amino-2-acetyl anthraquinone,
- Green chemistry
1. [1]
  [1] Zhang X S, Song X X, Li H, Zhang S L, Chen X B, Yu X H, Wang W. Angew Chem Int Ed, 2012, 51: 7282
2. [2]
  [2] Akiba K, Kashiwagi K, Ohyama Y, Yamamoto Y, Ohkata K. J Am Chem Soc, 1985, 107: 2721
3. [3]
  [3] Krasavin M, Busel A, Parchinsky V. Tetrahedron Lett, 2009, 50: 5945
4. [4]
  [4] Zhao Z K, Li R Z, Li Y, Chen G T (赵忠奎, 李仁志, 李宇, 陈广涛). CN Patent 102603547A. 2013
5. [5]
  [5] Epple G, Flohr H. DE Patent 2912570A1. 1979
6. [6]
  [6] Wilke K. US Patent 1830152. 1931
7. [7]
  [7] Li C S, Lacasse E. Tetrahedron Lett, 2002, 43: 3565
8. [8]
  [8] Vasilevsky S F, Gornostaev L M, Stepanov A A, Arnold E V, Alabugin I V. Tetrahedron Lett, 2007, 48: 1867
9. [9]
  [9] Churykau D H, Zinovich V G, Kulinkovich O G. Synlett, 2004, 11: 1949
10. [10]
  [10] Buechi G, Vederas J C. J Am Chem Soc, 1972, 27: 9128
11. [11]
  [11] Konwar D, Boruah R C, Sandhu J S. Chem Ind, 1989, (6): 191
12. [12]
  [12] Auricchio S, Bini A, Pastormerlo E, Truscello A M. Tetrahedron, 1997, 53: 10911
13. [13]
  [13] Kijima M, Nambu Y, Endo T. J Org Chem, 1985, 50: 1140
14. [14]
  [14] Mohatt J L, Hu L H, Finneran K T, Strathmann T J. Environ Sci Technol, 2011, 45: 4793
15. [15]
  [15] Angibaud P R, Venet M G, Filliers W, Broeckx R, Ligny Y A, Muller P, Poncelet V S, End D W. Eur J Org Chem, 2004, 2004: 479
16. [16]
  [16] Fan X S, Zhang Y M. Tetrahedron Lett, 2002, 43: 7001
17. [17]
  [17] Natale N R. Tetrahedron Lett, 1982, 23: 5009
18. [18]
  [18] Konwar D, Boruah R C, Sandhu J S, Baruah J N. Synth Commun, 1984, 14: 1053
19. [19]
  [19] Olah G A, Narang S C. Tetrahedron, 1982, 38: 2225
20. [20]
  [20] Walker G N. J Org Chem, 1962, 27: 1929
21. [21]
  [21] Oster T A, Harris T M. J Org Chem, 1983, 48: 4307
22. [22]
  [22] Caplan J F, Zheng R J, Blanchard J S, Vederas J C. Org Lett, 2000, 2: 3857
23. [23]
  [23] Charest M G, Siegel D R, Myers A G. J Am Chem Soc, 2005, 127: 8292
24. [24]
  [24] Zhao Z K, Li R Z, Li Y. Chin J Catal (赵忠奎, 李仁志, 李宇. 催化学报), 2014, 35: 319
25. [25]
  [25] MacMillan D W C. Nature, 2008, 455: 304
26. [26]
  [26] Nicewicz D A, MacMillan D W C. Science, 2008, 322: 77
27. [27]
  [27] Lamani M, Guralamata R S, Prabhu K R. Chem Commun, 2012, 48: 6583
28. [28]
  [28] de Vries J G, Mrsic N. Catal Sci Technol, 2011, 1: 51
29. [29]
  [29] Imada Y, Kitagawa T, Ohno T, Iida H, Naota T. Org Lett, 2010, 12: 32
30. [30]
  [30] Chen C X, Xu R, Li B. Sci China B, 2012, 55: 1257
31. [31]
  [31] Zhao Z K, Li R Z, Li Y. ScienceJet, 2013, 2: 41
32. [32]
  [32] Chen Q, Liang J Y, Wang S L, Wang D, Wang R. Chem Commun, 2013, 49: 1657
33. [33]
  [33] Kano T, Song S Y, Kubota Y L, Maruoka K. Angew Chem Int Ed, 2012, 51: 1191
34. [34]
  [34] Liu J, Yang Z G, Wang Z, Wang F, Chen X H, Liu X H, Feng X M, Su Z S, Hu C W. J Am Chem Soc, 2008, 130: 5654
1. [1]
  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
2. [2]
  Yinwu Su , Xuanwen Zheng , Jianghui Du , Boda Li , Tao Wang , Zhiyan Huang . Green Synthesis of 1,3-Dibromoacetone Using Halogen Exchange Method: Recommending a Basic Organic Synthesis Teaching Experiment. University Chemistry, 2024, 39(5): 307-314. doi: 10.3866/PKU.DXHX202311092
3. [3]
  Xue Dong , Xiaofu Sun , Shuaiqiang Jia , Shitao Han , Dawei Zhou , Ting Yao , Min Wang , Minghui Fang , Haihong Wu , Buxing Han . 碳修饰的铜催化剂实现安培级电流电化学还原CO₂制C₂₊产物. Acta Physico-Chimica Sinica, 2025, 41(3): 2404012-. doi: 10.3866/PKU.WHXB202404012
4. [4]
  Feng Han , Fuxian Wan , Ying Li , Congcong Zhang , Yuanhong Zhang , Chengxia Miao . Comprehensive Organic Chemistry Experiment: Phosphotungstic Acid-Catalyzed Direct Conversion of Triphenylmethanol for the Synthesis of Oxime Ethers. University Chemistry, 2025, 40(3): 342-348. doi: 10.12461/PKU.DXHX202405181
5. [5]
  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
6. [6]
  Zijian Zhao , Yanxin Shi , Shicheng Li , Wenhong Ruan , Fang Zhu , Jijun Jiang . A New Exploration of the Preparation of Polyacrylic Acid by Free Radical Polymerization Based on the Concept of Green Chemistry. University Chemistry, 2024, 39(5): 315-324. doi: 10.3866/PKU.DXHX202311094
7. [7]
  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
8. [8]
  Wenjiang LI , Pingli GUAN , Rui YU , Yuansheng CHENG , Xianwen WEI . C₆₀-MoP-C nanoflowers van der Waals heterojunctions and its electrocatalytic hydrogen evolution performance. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 771-781. doi: 10.11862/CJIC.20230289
9. [9]
  Jihua Deng , Xinshi Wu , Dichang Zhong . Exploration of Green Teaching and Ideological and Political Education in Chemical Experiment of “Preparation of Ammonium Ferrous Sulfate”. University Chemistry, 2024, 39(10): 325-329. doi: 10.12461/PKU.DXHX202405046
10. [10]
  Zihan Lin , Wanzhen Lin , Fa-Jie Chen . Electrochemical Modifications of Native Peptides. University Chemistry, 2025, 40(3): 318-327. doi: 10.12461/PKU.DXHX202406089
11. [11]
  Tingting Yu , Si Chen , Lianglong Sun , Tongtong Shi , Kai Sun , Xin Wang . Comprehensive Experimental Design for the Photochemical Synthesis, Analysis, and Characterization of Difluoropyrroles. University Chemistry, 2024, 39(11): 196-203. doi: 10.3866/PKU.DXHX202401022
12. [12]
  Yunchao Li , Shanying Chen , Ke Qi , Kangning Huo , Shuxin Li , Jingyi Li , Ying Wei , Louzhen Fan . A New Colloid Electrophoresis Experiment Incorporating Characteristics of Inquiry Learning and Ideological and Political Education. University Chemistry, 2024, 39(2): 47-51. doi: 10.3866/PKU.DXHX202308063
13. [13]
  Lu XU , Chengyu ZHANG , Wenjuan JI , Haiying YANG , Yunlong FU . Zinc metal-organic framework with high-density free carboxyl oxygen functionalized pore walls for targeted electrochemical sensing of paracetamol. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 907-918. doi: 10.11862/CJIC.20230431
14. [14]
  Zhilian Liu , Wengui Wang , Hongxiao Yang , Yu Cui , Shoufeng Wang . Ideological and Political Education Design for the Synthesis of Irinotecan Drug Intermediate 7-Ethyl Camptothecin. University Chemistry, 2024, 39(2): 89-93. doi: 10.3866/PKU.DXHX202306012
15. [15]
  Ling Liu , Haibin Wang , Genrong Qiang . Curriculum Ideological and Political Design for the Comprehensive Preparation Experiment of Ethyl Benzoate Synthesized from Benzyl Alcohol. University Chemistry, 2024, 39(2): 94-98. doi: 10.3866/PKU.DXHX202304080
16. [16]
  Yiming Lu , Xiang Xie , Xiaoqing Qiu , Yang Liu , Xinyuan Cheng . The New Year’s Eve of the Aviation Brake Material Family. University Chemistry, 2024, 39(9): 203-207. doi: 10.12461/PKU.DXHX202403061
17. [17]
  .
  CCS Chemistry 综述推荐│绿色氧化新思路：光/电催化助力有机物高效升级
  . CCS Chemistry, 2025, 7(10.31635/ccschem.024.202405369): -.
18. [18]
  Ruiyuan Xu , Yuxin Wang , Yuru Zhang , Wanmei Li . Who Destroyed Snowflake Castle. University Chemistry, 2024, 39(9): 224-228. doi: 10.12461/PKU.DXHX202311056
19. [19]
  Zelong LIANG , Shijia QIN , Pengfei GUO , Hang XU , Bin ZHAO . Synthesis and electrocatalytic CO₂ reduction performance of metal-organic framework catalysts loaded with silver particles. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 165-173. doi: 10.11862/CJIC.20240409
20. [20]
  Jing SU , Bingrong LI , Yiyan BAI , Wenjuan JI , Haiying YANG , Zhefeng Fan . Highly sensitive electrochemical dopamine sensor based on a highly stable In-based metal-organic framework with amino-enriched pores. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1337-1346. doi: 10.11862/CJIC.20230414

Get Citation

PDF

XML

Metrics

PDF Downloads(476)
Abstract views(742)
HTML views(20)

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