Citation: Zhang Xinming, Guo Yujun, Tao Guide, Zhang Wu. Aerobic Oxidation for the Synthesis of N-Substituted α-Hydroxyl Phenylacetamides Promoted by Base[J]. Chinese Journal of Organic Chemistry, ;2017, 37(11): 2993-2999. doi: 10.6023/cjoc201704037 shu

Aerobic Oxidation for the Synthesis of N-Substituted α-Hydroxyl Phenylacetamides Promoted by Base

College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000

Corresponding author: Zhang Wu, zhangwu@mail.ahnu.edu.cn
Received Date: 22 April 2017
Revised Date: 3 July 2017
Available Online: 7 November 2017
Fund Project: the National Natural Science Foundation of China 21272006Project supported by the National Natural Science Foundation of China (No. 21272006)

Figures(3)

α-Hydroxyl amides are important skeleton and valuable intermediates that present in many natural products, pharmaceutical active compounds, and organic functional materials. The main methods for synthesis of α-hydroxyl amides are either through amidation of α-hydroxyl acids, or by reduction of α-keto amides. Herein, a convenient potassium hydroxide/dimethyl sulfoxide promoted aerobic oxidation reaction to prepare N-substituted α-hydroxyl phenylacetamides is reported in good to high yields. 21 corresponding products were obtained and characterized by ¹H NMR, ¹³C NMR and HRMS. The molecular structure of 2-(2-bromophenyl)-2-hydroxy-N-(p-tolyl)acetamide (2a) was confirmed by using single-crystal X-ray analyses.
- α-hydroxyl amides,
- aerobic oxidation,
- synthesis,
- KOH-DMSO
1. [1]
  Pansare, S. V.; Ravi, R. G.; Jain, R. P. J. Org. Chem. 1998, 63, 4120. doi: 10.1021/jo9722820
2. [2]
  Chen, C. T.; Bettigeri, S.; Weng, S. S.; Pawar, V. D.; Lin, Y. H.; Liu, C. Y.; Lee, W. Z. J. Org. Chem. 2007, 72, 8175. doi: 10.1021/jo070575f
3. [3]
  Szymanski, W.; Westerbeek, A.; Janssen, D, B.; Feringa, B, L. Angew. Chem., Int. Ed. 2011, 50, 10712. doi: 10.1002/anie.201105164
4. [4]
  Zhang, M.; Imm, S.; Bahn, S.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2011, 50, 11197. doi: 10.1002/anie.v50.47
5. [5]
  Katritzky, A. R.; Singh, S. K.; Cai, C.; Bobrov, S. J. Org. Chem. 2006, 71, 3364. doi: 10.1021/jo052293q
6. [6]
  Pailloux, S.; Binyamin, I.; Deck, L. M.; Rapko, B. M.; Hay, B. P.; Duesler, E. N.; Paine, R. T. J. Org. Chem. 2007, 72, 9195. doi: 10.1021/jo701408y
7. [7]
  Nemoto, T.; Kakei, H.; Gnanadesikan, V.; Tosaki, S.; Ohshima, T.; Shibasaki, M. J. Am. Chem. Soc. 2002, 124, 14544. doi: 10.1021/ja028454e
8. [8]
  Kikugawa, Y.; Matsumoto, K.; Mitsui, K. J. Chem. Soc., Chem. Commun. 1992, 12, 921.
9. [9]
  Denmark, S. E.; Fan, Y. J. Org. Chem. 2005, 70, 9667. doi: 10.1021/jo050549m
10. [10]
  Yao, Y.; Li, W. D.; Tong, W. T.; Chen, J. X. Chin. J. Org. Chem. 2015, 35, 223(in Chinese).
11. [11]
  (a) Stahl, S. S. Angew. Chem., Int. Ed. 2004, 43, 3400.
  (b) Wendlandt, A. E.; Suess, A. M.; Stahl, S. S. Angew. Chem., Int. Ed. 2011, 50, 11062.
12. [12]
  (a) Gassman, P. G.; Halweg, K. M. J. Org. Chem. 1979, 44, 628.
  (b) Sereda, G.; Rajpara, V. Tetrahedron Lett. 2007, 48, 3417.
  (c) Hamano, M.; Nagy, K. D.; Jensen, K. F. Chem. Commun. 2012, 48, 2086.
  (d) Zheng, G.; Liu, H.; Wang, M. Chin. J. Chem. 2016, 34, 519.
  (e) Zhang, J.; Jiang, Z. Q.; Zhao, D.; He, G. Z.; Zhou, S. L.; Han, S. Q. Chin. J. Chem. 2013, 31, 794.
13. [13]
  Watanabe, T.; Ishikawa, T. Tetrahedron Lett. 1999, 40, 7795. doi: 10.1016/S0040-4039(99)01618-4
14. [14]
  Song, B. G.; Wang, S. Y.; Sun, C. Y.; Deng, H. M.; Xu, B. Tetrahedron Lett. 2007, 48, 8982. doi: 10.1016/j.tetlet.2007.10.099
15. [15]
  (a) Trofimov, B. A.; Malysheva, S. F.; Gusarova, N. K.; Kuimov, V. A.; Belogorlova, N. A.; Sukhov, B. G. Tetrahedron Lett. 2008, 49, 3480.
  (b) Duan, Z. G.; Ranjit, S.; Liu, X. G. Org. Lett. 2010, 12, 2430.
  (c) Yuan, Y.; Thome, I.; Kim, S. H.; Chen, D.; Beyer, A.; Bonnamour, J.; Zuidema, E.; Chang, S.; Bolm, C. Adv. Synth. Catal. 2010, 352, 2892.
  (d) Beyer, A.; Reucher, C. M. M.; Bolm, C. Org. Lett. 2011, 13, 2876.
16. [16]
  (a) Lipton, S. H.; Bodwell, C. E. J. Agric. Food Chem. 1976, 24, 26.
  (b) Gogoi, P.; Sarmah, G. K.; Konwar, D. J. Org. Chem. 2004, 69, 5153.
  (c) Le, H. V.; Ganem, B. Org. Lett, 2011, 13, 2584.
  (d) Chaudhari, M. B.; Sutar, Y.; Malpathak, S.; Hazra, A.; Gnanaprakasam, B. Org. Lett. 2017, 19, 3628.
17. [17]
  (a) Avramoff, M.; Sprinzak, Y. J. Am. Chem. Soc. 1963, 85, 1655.
  (b) Wasserman, H. H.; Lipahutz, B. H. Tetrahedron Lett. 1975, 16, 1731.
18. [18]
  Sun, J.; Liu, B. X.; Xu, B. RSC Adv. 2013, 3, 5824. doi: 10.1039/c3ra40657a
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