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Microwave Irradiation Assisted Selective Synthesis of 4,6-Diaryl-3,4- dihydropyrimidin-2(1H)-ones and Pyrimidin-2(1H)-ones

  • An Lin ,
  • Zhang ling ,
  • Zheng Youguang ,
  • Xue Yunsheng ,
  • Mou Jie ,
  • Liu Ling ,
  • Liu Yi
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  • School of Pharmacy, Xuzhou Medical College, Xuzhou 221004

Received date: 2011-11-28

  Revised date: 2011-12-22

  Online published: 2012-02-04

Supported by

Project supported by the Natural Science Foundation of the Jiangsu Higher Education Institutions of China (No. 11KJB350005), the Presidential Foundation of Xuzhou Medical College of China (No. 2010YKJ008), the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD), and the Natural Science Foundation of Xuzhou City (Nos. XF11C062, XZZD1055).

Abstract

Under microwave irradiation, the three-component reaction of aromatic aldehydes, substituted acetophenones and urea in N,N-dimethyl formamide (DMF) resulted in 4,6-diaryl-3,4-dihydro-pyrimidin-2(1H)-ones in 68%~84% yields. In the presence of chlorotrimethylsilane, the three-component reactions gave the corresponding dehydrogenated 4,6-diarylpyrimidin- 2(1H)-ones in satisfactory yields (66%~87%). This method of microwave irradiation for the preparation of 4,6-diaryl pyrimidin-2(1H)-ones was simple, efficient and reaction time-saving.

Cite this article

An Lin , Zhang ling , Zheng Youguang , Xue Yunsheng , Mou Jie , Liu Ling , Liu Yi . Microwave Irradiation Assisted Selective Synthesis of 4,6-Diaryl-3,4- dihydropyrimidin-2(1H)-ones and Pyrimidin-2(1H)-ones[J]. Chinese Journal of Organic Chemistry, 2012 , 32(06) : 1108 -1111 . DOI: 10.6023/cjoc1111281

References

[1] Atwal, K. S.; Swanson, B. N.; Unger, S. E.; Floyd, D. M.; Moreland,S.; Hedberg, A.; O'Reilly, B. C. J. Med. Chem. 1991, 34(2),806.
[2] Kappe, C. O.; Fabian, W. M. F. Tetrahedron 1997, 53(8), 2803.
[3] Atwal, K. S.; Rovnyak, G. C.; O'Reilly, B. C.; Schwartz, J. J. Org.Chem. 1989, 54(25), 5898.
[4] Mayer, T. U.; Kapoor, T. M.; Haggarty, S. J.; King, R. W.;Schreiber, S. L.; Mitchison, T. J. Science. 1999, 2886(541), 971.  
[5] Hu, E. H.; Sidler, D. R.; Dolling, U. H. J. Org. Chem. 1998, 63(10),3454.
[6] Ma, Y.; Qian, C. T.; Wang, L. M.; Yang, M. J. Org. Chem. 2000,65(12), 3864.  
[7] Ranu, B. C.; Hajra, A.; Jana, U. J. Org. Chem. 2000, 65(19), 6270.  
[8] Lu, J.; Wang, F.-L.; Bai, Y-J.; Li, W.-H. Chin. J. Org. Chem. 2002,22, 111 (in Chinese).(路军, 王飞利, 白银娟, 李万华, 有机化学, 2002, 22, 111.)
[9] Salehi, P.; Dabiri, M.; Zolfigol, M.; Fard, M. A. B. TetrahedronLett. 2003, 44(14), 2889.  
[10] Niknam, K.; Zolfigol, M. A.; Hossieninejad, Z.; Daneshvar, N. J.Chin. Catal. 2007, 28(7), 591 (in Chinese).(Niknam, K.; Zolfigol, M. A.; Hossieninejad, Z.; Daneshvar, N., 催化学报, 2007, 28(7), 591.)
[11] Tang, W.-Y.; Jiang, H. J.; Zhuang, Y.-G.; Hong, Z.; Huang, G.-B.Sci. Technol. Eng. 2010, 10(14), 3534 (in Chinese).(唐文渊, 蒋华江, 庄玉国, 洪志, 黄国波, 科学技术与工程,2010, 10(14), 3534.)  
[12] Gupta, R.; Gupta ,A. K.; Paul, S. Indian J. Chem. 1995, 34B, 151.
[13] Stefani, H. A.; Gatti, P. M. Synth. Commum. 2000, 30(12), 2165.  
[14] Wipf, P.; Cunningham, A. Tetrahedron Lett. 1995, 36(43), 7819.  
[15] Studer, A.; Hadida, S.; Ferritto, R.; Kim, S. Y.; Jeger, P.; Wipf, P.;Curran, D. P. J. Org. Chem. 1997, 275(5301), 823.  
[16] Stadler, A., Kappe, C. O. J. Comb. Chem. 2001, 3(6), 624.
[17] Shaabani, A.; Bazgir, A. Tetrahedron Lett. 2004, 45(12), 2575.
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