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Chinese Journal of Organic Chemistry >

2012 , Vol. 32 >Issue 9: 1732 - 1735

DOI: https://doi.org/10.6023/cjoc1202261

Notes

Microwave-Assisted Ionic Liquid Catalyzed One-Pot Three-Component Synthesis of 3-{1-[2-(4-Arylthiazol-2-yl)-hydrazono]ethyl}-2H-chromen-2-one

  • Zhang Dongnuan ,
  • Li Jitai ,
  • Liu Huimin ,
  • Song Yali ,
  • Zhang Yingqun ,
  • Yuan Mingyue
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  • a Key Laboratory of Analyzed Science and Technology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding 071002;
    b College of Science, Agricultural University of Hebei, Baoding 071001;
    c College of Pharmaceutical Sciences, Hebei University, Baoding 071002

Received date: 2011-02-26

  Revised date: 2012-06-01

  Online published: 2012-05-12

Supported by

Project supported by the Science and Technology Department of Hebei Province (No.11276434) and the Science and Technology Bureau of Baoding City (No.10ZF104)

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Abstract

A series of 3-{1-[2-(4-arylthiazol-2-yl)hydrazono]ethyl}-2H-chromen-2-ones were synthesized with 85%～95% yields via the one-pot three-component reactions of acetyl coumarins, thiosemicarbazide and phenacyl bromide catalyzed by acidic ionic liquid under microwave irradiation. This method provides several advantages such as high yields, easy work-up and environmental friendly, and the catalyst can be recycled.

Key words： acidic ionic liquid; 3-{1-[2-(4-arylthiazol-2-yl)hydrazono]ethyl}-2H-chromen-2-one; microwave irradiation; synthesis

Cite this article

Zhang Dongnuan , Li Jitai , Liu Huimin , Song Yali , Zhang Yingqun , Yuan Mingyue . Microwave-Assisted Ionic Liquid Catalyzed One-Pot Three-Component Synthesis of 3-{1-[2-(4-Arylthiazol-2-yl)-hydrazono]ethyl}-2H-chromen-2-one[J]. Chinese Journal of Organic Chemistry, 2012 , 32(9) : 1732 -1735 . DOI: 10.6023/cjoc1202261

References

[1] Wang, Y. Z. J. China Pharm. 1992, 3, 47 (in Chinese). (王应庄, 中国药房, 1992, 3, 47.)

[2] Patt, W. C.; Hamilton, H. W.; Taylor, M. D. J. Med. Chem. 1992, 35, 2562.

[3] Zhong, W.; Xiao, Y. H.; Xiao, X. M. Chin. J. Clin. Pharmacol. 2006, 22, 35 (in Chinese).(钟巍, 肖永红, 肖秀美, 李耘, 中国临床药理学杂志, 2006, 22, 35.)

[4] Bell, F. W.; Cantrell, A. S.; Hogberg, M. J. Med. Chem. 1995, 38, 4929.

[5] Roger, D. B. Chem. Rev. 1964, 64, 229.

[6] Yuan, M. Y.; Zhang, D. N.; Yan, H. F.; Liu, W. H.; Li, D. F.; Zhang, Y. Q. Chin. J. Org. Chem. 2011, 31, 1930 (in Chinese).(袁明月, 张冬暖, 闫红飞, 刘伟华, 李德富, 张英群, 有机化学, 2011, 31, 1930.)

[7] (a) Dallinger, D.; Kappe, C. O. Chem. Rev. 2007, 107, 2563.

(b) Kappe, C. O. Angew. Chem., Int. Ed. 2004, 43, 6250.

(c) Wiesbrock, F.; Hoogenboom, R.; Schubert, U. S. Macromol. Rapid Commun. 2004, 25, 1739.

(d) Nuchter, M.; Ondruschka, B.; Bonrath, W.; Gum, A. Green Chem. 2004, 6, 128.  

(e) Wang, J.; Jiang, F. C. Chin. J. Org. Chem. 2002, 22, 212 (in Chinese).(王静, 姜凤超, 有机化学, 2002, 22, 212.)

[8] (a) Cetinkaya, E.; Alici, B.; Gok, Y. J. Chemother. 1999, 11, 83.

(b) Gudmundson, K. S.; Tidwell, J.; Lippa, N.; Koszalka. G. W.; Draanen, N. V.; Ptak, R. G.; Drach, J. C.; Townsend, L. B. J. Med. Chem. 2000, 43, 2464.

[9] Zhang, D. N.; Li, J. T.; Song, Y. L.; Chen, G. F. Lett. Org. Chem. 2011, 8, 385.

[10] Zhang, D, N.; Li, J. T.; Song, Y. L.; Liu, H. M.; Li, H. Y. Ultrason. Sonochem. 2012, 9, 475.

[11] Tang, S. W.; Scurto, A. M.; Subramaniam, B. J. Catal. 2009, 268, 243.

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