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Chinese Journal of Organic Chemistry >

2014 , Vol. 34 >Issue 8: 1669 - 1672

DOI: https://doi.org/10.6023/cjoc201402018

Notes

Synthesis of C(5)-(p-Toluoyl substituted)-3,4-dihydropyrimi- dinones (or -thiones) via Biginelli Reaction Promoted with Microwave Irradiation under Solvent-Free Conditions

  • Li Li ,
  • Liu Qingjian ,
  • Sui Xueyan
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  • College of Chemistry, Chemical Engineering and Materials Science, Shandong Normal University, Jinan 250014

Received date: 2014-02-17

  Revised date: 2014-03-13

  Online published: 2014-04-28

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Abstract

The Biginelli reaction, which involves the one-pot acid catalyzed cyclocondensation of ethyl acetoacetate, urea, and arylaldehyde, was first discovered by Italian chemist Pietro Biginelli about 120 years ago. A large number researchers have shown persistent attention to the study of Biginelli reaction on account of its significant biological and pharmaceutical activities and diversity of structural changes of dihydropyrimidines (DHPMs) and its derivatives. Herein, the synthesis of C(5)-(p-toluoyl)-3,4-dihydropyrimidin-2(1H)-ones (or -thiones) via Biginelli reaction has been accomplished from aldehydes, p-toluoylacetone, and urea or thiourea in the presence of TsOH promoted with microwave irradiation under solvent-free conditions in good yields and high purity without chromatographic separation.

Key words： Biginelli reaction; 3,4-dihydropyrimidin-2(1H)-ones (or -thiones); β-diketone; microwave irradittion

Cite this article

Li Li , Liu Qingjian , Sui Xueyan . Synthesis of C(5)-(p-Toluoyl substituted)-3,4-dihydropyrimi- dinones (or -thiones) via Biginelli Reaction Promoted with Microwave Irradiation under Solvent-Free Conditions[J]. Chinese Journal of Organic Chemistry, 2014 , 34(8) : 1669 -1672 . DOI: 10.6023/cjoc201402018

References

[1] Kappe, C. O. QSAR Comb. Sci. 2003, 22, 630.
[2] Kaan, H. Y. K.; Ulaganathan, V. R. O.; Prokopcov, H.; Dallinger, D.; Kappe, C. O.; Kozielski, J. F. J. Med. Chem. 2010, 5, 1560.
[3] Kappe, C. O. Eur. J. Med. Chem. 2000, 35, 1043.
[4] Kappe, C. O.; Stadler, A. Microwaves in Organic and Medicinal Chemistry, Wiley-VCH, Weinheim, 2005, p. 410.
[5] Nagarathnam, D.; Miao, S. W.; Lagu, B.; Chiu, G.; Fang, J.; Murali, D. T. G.; Zhang, J. J. Med. Chem. 1999, 42, 4764.
[6] Murali, D. T. G.; Nagarathnam, D.; Marzabadi, M. R.; Wong, W. C.; Miao, S. W.; Zhang, F. Q. J. Med. Chem. 1999, 42, 4778.
[7] Lagu, B.; Tian, D.; Nagarathnam, D.; Marzabadi, M. R.; Dhar, T. G. M.; Jeon, Y. T. J. Med. Chem. 1999, 42, 4794.
[8] Wong, W. C.; Sun, W.; Lagu, B.; Tian D.; Marzabadi, M. R.; Zhang, F.; Nagarathnam, D.; Miao, S. W.; Wetzel, J. M.; Peng, J. J. Med. Chem. 1999, 42, 4804.
[9] Lagu, B.; Tian, D.; Chiu, G.; Nagarathnam, D.; Fang, J.; Shen, Q.; Forray, C.; Ransom, R. W.; Chang, R. S. L.; Vyas, K. P. Bioorg. Med. Chem. Lett. 2000, 10, 175.
[10] Barrow, J. C.; Glass, K. L.; Selnick, H. G.; Freidinger, R. M.; Chang, R. S .L.; O'Malley, S. S.; Woyden, C. Bioorg. Med. Chem. Lett. 2000, 10, 1917.
[11] Mayer, T. U.; Kapoor, T. M.; Haggarty, S. J.; King, R. W.; Schreiber, S. L.; Mitchison, T. J. Science 1999, 286, 971.
[12] Deres, K.; Schröder, C. H.; Paessens, A.; Goldmann, S.; Hacker, H. J.; Weber, O.; Kraemer, T.; Niewoehner, U.; Pleiss, U. Science 2003, 299, 893.
[13] Heys, L.; Moore, C. G.; Murphy, P. J. Chem. Soc. Rev. 2000, 29, 57.
[14] Barluenga, J.; Tomas, M.; Rubio, V.; Gotor, V. J. Chem. Soc. 1995, 16, 1369.
[15] Aron, Z. D.; Overman, L. E. Chem. Commun. 2004, 34, 253.
[16] Wang, D.-C.; Yuan, T.-F.; Yang, X.-N.; Qu, G.-R. Chin. J. Org. Chem. 2007, 27, 1034 (in Chinese).
(王东超, 袁腾飞, 杨西宁, 渠桂荣, 有机化学, 2007, 27, 1034.)
[17] Sun, S.-Q.; Li, Y.-J.; Zhang, Z.-G.; Yu, S.-J.; Sun, P.; Zhou, X.-X. J. Liaoning Normal Univ.2011, 34, 4 (in Chinese).
(孙淑琴, 李英俊, 张治广, 于世钧, 孙鹏, 周晓霞, 辽宁师范大学学报, 2011, 34, 4.)
[18] Stadler, A.; Kappe, C. O. J. Chem. Soc., Perkin. Trans. 2 2000, 1363.
[19] Fu, N.-Y.; Yuan, Y.-F.; Pang, M.-L.; Wei, B.; Guo, J. Chem. J. Chin. Univ. 2003, 24, 79 (in Chinese).
(傅南雁, 袁耀锋, 庞美丽, 卫兵, 郭建, 高等化学学报, 2003, 24, 79.)
[20] Shutalev, A. D.; Sivova, N. V. Chem. Heterocycl. Compd. 1988, 34, 848.
[21] Liu, Y.; Liu, X.-L.; Huang, G.-W.; Wang, Q. J. Jiangxi Univ. 2010, 34, 4 (in Chinese).
(刘园, 刘晓玲, 黄国文, 王清, 江西师范大学学报, 2010, 34, 4.)
[22] Peng, J.; Deng, Y. Chin. J. Org. Chem. 2002, 22, 71 (in Chinese).
(彭建, 邓宇, 有机化学, 2002, 22, 71.)
[23] Ma, J.-G.; Zhang, J.-M.; Zhou, J.-H. Shandong Sci. 2011, 24, 22 (in Chinese).
(马金广, 张纪明, 周建华, 山东科学, 2011, 24, 22.)
[24] Crystal data for 6-Methyl-5-(4-methylbenzoyl)-4-(3-nitrophenyl)- 3,4-dihydropyrimidin-2(1H)-one (12). m.p. 217.1～220.3℃. C19H17N3O4, Mr=351.36, triclinic, P-1, a=7.381(3) Å, α=65.390(5)°, b=11.938(4) Å, β=79.186(5)°, c=13.176(5) Å, γ=81.968(5)°, V=1034.4(6) A3, Z=21, Dcalcd=1.270 mg/m-3, T=298(2) K, radiation=0.71073 Å, final R indices[I>2σ(I)], R1=0.0755, wR2=0.1728, R indices (all data), R1=0.1428, wR2=0.2038, for all data reflections collected/unique 5422/3792[R(int)=0.0278], GOF=1.016. Diffraction data were measured on a Siemens 4 Circle single-crystal X-ray diffractometer.
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