Citation: Rao Honghong, Quan Zhengjun, Bai Lin, Ye Helin. Progress on the Synthesis of Enantiomerically Pure 3,4-Dihydropyrimidin-2-one Derivatives[J]. Chinese Journal of Organic Chemistry, ;2016, 36(2): 283-296. doi: 10.6023/cjoc201507001 shu

Progress on the Synthesis of Enantiomerically Pure 3,4-Dihydropyrimidin-2-one Derivatives

  • Corresponding author: Rao Honghong, 
  • Received Date: 1 July 2015
    Available Online: 14 September 2015

    Fund Project: 国家自然科学基金(Nos. 21265009, 21362032)资助项目. (Nos. 21265009, 21362032)

  • 3,4-Dihydropyrimidinethiones are chiral molecules, however, only racemic products are isolated in the most reported Biginelli reactions. It has been proved that the absolute configuration of the C(4) stereogenic center has significant influence on the biological activity. The development in the accessing of optically active 3,4-dihydropyrimidinethiones focusing on the recent advances in the asymmetric catalytic Biginelli reactions is summarized.
  • 加载中
    1. [1]

      [1] Biginelli, P. Gazz. Chim. Ital. 1893, 23, 360.

    2. [2]

      [2] Atwal, K. S.; Rovnyak, G. C.; Schwartz, J.; Moreland, S.; Hedberg, A.; Gougoutas, J. Z.; Malley, M. F.; Floyd, D. M. J. Med. Chem. 1990, 33, 1510.

    3. [3]

      [3] (a) Rovnyak, G. C.; Atwal, K. S.; Hedberg, A.; Kimball, S. D.; Moreland, S.; Gougoutas, J .Z.; O'Reilly, B. C.; Schwartz, J.; Malley, M. F. J. Med. Chem. 1992, 35, 3254. (b) Deres, K.; Schroder, C. H.; Paessens, A.; Goldmann, S.; Hacker, H. J.; Weber, O.; Kraemer, T.; Niewoehner, U.; Pleiss, U.; Stoltefuss, J.; Graef, E.; Koletzki, D.; Masantschek, R. N. A.; Reimann, A.; Jaeger, R.; Groâ, R.; Beckermann, B.; Schlemmer, K.-H.; Haebich, D.; Rubsamen-Waigmann, H. Science 2003, 299, 893. (d) Kappe, C. O. Eur. J. Med. Chem. 2000, 35, 1043. (c) Lewis, R. W.; Mabry, J.; Polisar, J. G.; Eagen, K. P.; Ganem, B.; Hess, G. P. Biochemistry 2010, 49, 4841. (d) Wan, J.-P.; Pan, Y. Mini-Rev. Med. Chem. 2012, 12, 337.

    4. [4]

      [4] Hurst, E. W.; Ann. N. Y. Ann. NY Acad. Sci. 1962, 98, 275.

    5. [5]

      [5] (a) Kappe, C. O. Tetrahedron 1993, 49, 6937. (b) Kappe, C. O. Acc. Chem. Res. 2000, 33, 879. (c) Wan, J.-P.; Liu, Y. Synthesis 2010, 2010, 3943.

    6. [6]

      [6] 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, 806.

    7. [7]

      [7] Barrow, J. C.; Nantermet, P. G.; Selnick, H. G.; Glass, K. L.; Rittle, K. E.; Gilbert, K. F.; Steele, T. G.; Homnick, C. F.; Freidinger, R. M.; Ransom, R. W.; Kling, P.; Reiss, D.; Broten, T. P.; Schorn, T. W.; Chang, R. S. L.; O′Malley, S. S.; Olah, T. V.; Ellis, J. D.; Barrish, A.; Kassahun, K.; Leppert, P.; Nagarathnam, D.; Forray, C. J. Med. Chem. 2000, 43, 2703.

    8. [8]

      [8] (a) Maliga, Z.; Kapoor, T. M.; Mitchison, T. J. Chem. Biol. 2002, 9, 989. (b) Debonis, S.; Simorre, J. P.; Crevel, I.; Lebeau, L.; Skoufias, D. A.; Blangy, A.; Ebel, C.; Gans, P.; Cross, R.; Hackney, D. D.; Wade, R. H.; Kozielski, F. Biochemistry 2003, 42, 338.

    9. [9]

      [9] (a) Du, B.-X.; Quan, Z.-J.; Da, Y.-X.; Zhang, Z.; Wang, X.-C. Adv. Synth. Catal. 2015, 357, 1270. (b) Quan, Z.-J.; Lv,Y.; Jing, F.-Q.; Jia, X.-D.; Huo, C.-D.; Wang, X.-C. Adv. Synth. Catal. 2014, 356, 325. (c) Quan, Z.-J.; Jing, F.-Q.; Zhang, Z.; Da, Y.-X.; Wang, X.-C. Eur. J. Org. Chem. 2013, 2013, 7175. (d) Quan, Z.-J.; Lv, Y.; Wang, Z.-J.; Zhang, Z.; Da, Y.-X.; Wang, X.-C. Tetrahedron Lett. 2013, 54, 1884. (e) Quan, Z.-J.; Zhang, Z.; Da, Y.-X.; Wang, X.-C. Chin. J. Org. Chem. 2009, 29, 876 (in Chinese). (权正军, 张彰, 达玉霞, 王喜存, 有机化学, 2009, 29, 876). (f) Wang, X. C.; Quan, Z. J.; Wang, F.; Wang, M. G.; Zhang, Z.; Li, Z. Synth. Commun. 2006, 36, 451.

    10. [10]

      [10] (a) Gong, L. Z.; Chen, X. H.; Xu, X.-Y. Chem. Eur. J. 2007, 13, 8920. (b) Heravi, M. M.; Asadi, S.; Lashkariani, B. M. Mol. Diversity 2013, 17, 389. (c) Wan, J.-P.; Lin, F.; Liu, Y. Curr. Org. Chem. 2014, 18, 687.

    11. [11]

      [11] Atwal, K. S.; Rovnyak, G. C.; Kimball, S. D.; Floyd, D. M.; Moreland, S.; Swanson, B. N.; Gougoutas, J. Z.; Schwartz, J.; Smillie, K. M.; Malley, M. F. J. Med. Chem. 1990, 33, 2629.

    12. [12]

      [12] Dondoni, A.; Massi, A.; Sabbatini, S. Tetrahedron Lett. 2002, 43, 5913.

    13. [13]

      [13] (a) Chartrain, C. M.; Ikemoto, N.; Taylor, C. S. WO 9907695, 1999 [Chem. Abstr. 1999, 130, 182478]. (b) Sidler, D. R.; Barta, N.; Li, W.; Hu, E.; Matty, L.; Ikemoto, N.; Campbell, J. S.; Chartrain, M.; Gbewonyo, K.; Boyd, R.; Corley, E. G.; Ball, R. G.; Larsen, R. D.; Reider, P. J. Can. J. Chem. 2002, 80, 646.

    14. [14]

      [14] Prasad, A. K.; Mukherjee, C.; Singh, S. K.; Brahma, R.; Singh, R.; Saxena, R. K.; Olsen, C. E.; Parmar, V. S. J. Mol. Catal. B: Enzyme 2006, 40, 93.

    15. [15]

      [15] Dondoni, A.; Massi, A.; Minghini, E.; Sabbatini, S.; Bertolasi, V. J. Org. Chem. 2003, 68, 6172.

    16. [16]

      [16] Dondoni, A.; Massi, A. Acc. Chem. Res. 2006, 39, 451.

    17. [17]

      [17] Kappe, C. O.; Uray, G.; Roschger, P.; Lindner, W.; Kratky, C.; Keller, W. Tetrahedron 1992, 48, 5473.

    18. [18]

      [18] Lou, S.; Taoka, B. M.; Ting, A.; Schaus, S. E. J. Am. Chem. Soc. 2005, 127, 11256.

    19. [19]

      [19] Lou, S.; Dai, P.; Schaus, S. E. J. Org. Chem. 2007, 72, 9998.

    20. [20]

      [20] Goss, J. M.; Schaus, S. E. J. Org. Chem. 2008, 73, 7651.

    21. [21]

      [21] Muñoz-Muñiz, O.; Juaristi, E. ARKIVOC 2003, xi, 16.

    22. [22]

      [22] Huang, Y.; Yang, F.; Zhu, C. J. Am. Chem. Soc. 2005, 127, 16386.

    23. [23]

      [23] Cai, Y;-F.; Yang, H.-M.; Li, L.; Jiang, K.-Z.; Lai, G.-Q.; Jiang, J.-X.; Xu, L.-W. Eur. J. Org. Chem. 2010, 2010, 4986.

    24. [24]

      [24] Karthikeyan, P.; Aswar, S. A.; Muskawar, P. N.; Bhagat, P. R.; Kumar, S. S. J. Organomet. Chem. 2013, 723, 154.

    25. [25]

      [25] (a) Stephen, J. C. Chem. Eur. J. 2006, 12, 5418. (b) Phillips A. M. F. Eur. J. Org. Chem. 2014, 2014, 7291.

    26. [26]

      [26] Chen, X.-H.; Xu, X.-Y.; Liu, H.; Cun, L.-F.; Gong, L.-Z. J. Am. Chem. Soc. 2006, 128, 14802.

    27. [27]

      [27] (a) Li, N.; Chen, X.-H.; Song, J.; Luo, S.-W.; Fan, W.; Gong, L.-Z. J. Am. Chem. Soc. 2009, 131, 15301. (b) Yu, J.; Shi, F.; Gong, L.-Z. Acc. Chem. Res. 2011, 44, 1156.

    28. [28]

      [28] Xu, F.; Huang, D.; Lin, X.; Wang, Y. Org. Biomol. Chem. 2012, 10, 4467.

    29. [29]

      [29] González-Olvera, R.; Demare, P.; Regla, I.; Juaristi, E. ARKIVOC 2008, vi, 61.

    30. [30]

      [30] Xin, J.; Chang, L.; Hou, Z.; Shang, D.; Liu, X.; Feng, X. Chem. Eur. J. 2008, 14, 3177.

    31. [31]

      [31] Li, Z. Y.; Xing, H. J.; Huang, G. L.; Sun, X. Q.; Jiang, J. L.; Wang, L. Y. Sci. China Chem. 2011, 54, 1726.

    32. [32]

      [32] Saha, S.; Moorthy, J. N. J. Org. Chem. 2011, 76, 396.

    33. [33]

      [33] Wu, Y.-Y.; Chai, Z.; Liu, X.-Y.; Zhao, G.; Wang, S.-W. Eur. J. Org. Chem. 2009, 904.

    34. [34]

      [34] Sohn, J.-H.; Choi, H.-M.; Lee, S.; Joung, S.; Lee, H.-Y. Eur. J. Org. Chem. 2009, 3858.

    35. [35]

      [35] (a) List, B.; Lerner, R. A.; Barbas, C. F. J. Am. Chem. Soc. 2000, 122, 2395. (b) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243. (c) Yang, D. Acc. Chem. Res. 2004, 37, 497. (d) Shi, Y. Acc. Chem. Res. 2004, 37, 488. (d) Wang, Y.; Han, R. G.; Zhao, Y. L.; Yang, S.; Xu, P. F. Dixon, D. J. Angew. Chem., Int. Ed. 2009, 48, 9834.

    36. [36]

      [36] Wang, Y.; Yang, H.; Yu, J.; Miao, Z.; Chen, R. Adv. Synth. Catal. 2009, 351, 3057.

    37. [37]

      [37] Wang, Y.; Yu, J.; Miao, Z.; Chen, R. Org. Biomol. Chem. 2011, 9, 3050.

    38. [38]

      [38] Frings, M.; Thomé, I.; Bolm, C. Beilstein J. Org. Chem. 2012, 8, 1443.

    39. [39]

      [39] Ding, D.; Zhao, C.-G. Eur. J. Org. Chem. 2010, 2010, 3802.

    40. [40]

      [40] Xu, D.-Z.; Li, H.; Wang, Y. Tetrahedron 2012, 68, 7867.

    41. [41]

      [41] An, D.; Fan, Y.-S.; Gao, Y.; Zhu, Z.-Q.; Zheng, L.-Y.; Zhang, S.-Q. Eur. J. Org. Chem. 2014, 2014, 301.

  • 加载中
    1. [1]

      Hong Lu Yidie Zhai Xingxing Cheng Yujia Gao Qing Wei Hao Wei . Advancements and Expansions in the Proline-Catalyzed Asymmetric Aldol Reaction. University Chemistry, 2024, 39(5): 154-162. doi: 10.3866/PKU.DXHX202310074

    2. [2]

      Ke QIAOYanlin LIShengli HUANGGuoyu YANG . Advancements in asymmetric catalysis employing chiral iridium (ruthenium) complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2091-2104. doi: 10.11862/CJIC.20240265

    3. [3]

      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

    4. [4]

      Dan Liu . 可见光-有机小分子协同催化的不对称自由基反应研究进展. University Chemistry, 2025, 40(6): 118-128. doi: 10.12461/PKU.DXHX202408101

    5. [5]

      Tingyu Zhu Hui Zhang Wenwei Zhang . Exploration and Practice of Ideological and Political Education in the Course of Experiments on Chemical Functional Molecules: Synthesis and Catalytic Performance Study of Chiral Mn(III)Cl-Salen Complex. University Chemistry, 2024, 39(4): 75-80. doi: 10.3866/PKU.DXHX202311011

    6. [6]

      Weina Wang Lixia Feng Fengyi Liu Wenliang Wang . Computational Chemistry Experiments in Facilitating the Study of Organic Reaction Mechanism: A Case Study of Electrophilic Addition of HCl to Asymmetric Alkenes. University Chemistry, 2025, 40(3): 206-214. doi: 10.12461/PKU.DXHX202407022

    7. [7]

      Qianwen Han Tenglong Zhu Qiuqiu Lü Mahong Yu Qin Zhong . 氢电极支撑可逆固体氧化物电池性能及电化学不对称性优化. Acta Physico-Chimica Sinica, 2025, 41(1): 2309037-. doi: 10.3866/PKU.WHXB202309037

    8. [8]

      Yue Zhao Yanfei Li Tao Xiong . Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones. University Chemistry, 2024, 39(4): 280-285. doi: 10.3866/PKU.DXHX202309001

    9. [9]

      Ran HUOZhaohui ZHANGXi SULong CHEN . Research progress on multivariate two dimensional conjugated metal organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2063-2074. doi: 10.11862/CJIC.20240195

    10. [10]

      Guojie Xu Fang Yu Yunxia Wang Meng Sun . Introduction to Metal-Catalyzed β-Carbon Elimination Reaction of Cyclopropenones. University Chemistry, 2024, 39(8): 169-173. doi: 10.3866/PKU.DXHX202401060

    11. [11]

      Tianlong Zhang Rongling Zhang Hongsheng Tang Yan Li Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006

    12. [12]

      Haodong JINQingqing LIUChaoyang SHIDanyang WEIJie YUXuhui XUMingli XU . NiCu/ZnO heterostructure photothermal electrocatalyst for efficient hydrogen evolution reaction. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1068-1082. doi: 10.11862/CJIC.20250048

    13. [13]

      . . Chinese Journal of Inorganic Chemistry, 2024, 40(11): 0-0.

    14. [14]

      Heng Zhang . Determination of All Rate Constants in the Enzyme Catalyzed Reactions Based on Michaelis-Menten Mechanism. University Chemistry, 2024, 39(4): 395-400. doi: 10.3866/PKU.DXHX202310047

    15. [15]

      Renxiao Liang Zhe Zhong Zhangling Jin Lijuan Shi Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024

    16. [16]

      Yuanyi Lu Jun Zhao Hongshuang Li . Silver-Catalyzed Ring-Opening Minisci Reaction: Developing a Teaching Experiment Suitable for Undergraduates. University Chemistry, 2024, 39(11): 225-231. doi: 10.3866/PKU.DXHX202401088

    17. [17]

      Zhuoyan Lv Yangming Ding Leilei Kang Lin Li Xiao Yan Liu Aiqin Wang Tao Zhang . Light-Enhanced Direct Epoxidation of Propylene by Molecular Oxygen over CuOx/TiO2 Catalyst. Acta Physico-Chimica Sinica, 2025, 41(4): 100038-. doi: 10.3866/PKU.WHXB202408015

    18. [18]

      Hongting Yan Aili Feng Rongxiu Zhu Lei Liu Dongju Zhang . Reexamination of the Iodine-Catalyzed Chlorination Reaction of Chlorobenzene Using Computational Chemistry Methods. University Chemistry, 2025, 40(3): 16-22. doi: 10.12461/PKU.DXHX202403010

    19. [19]

      Aili Feng Xin Lu Peng Liu Dongju Zhang . Computational Chemistry Study of Acid-Catalyzed Esterification Reactions between Carboxylic Acids and Alcohols. University Chemistry, 2025, 40(3): 92-99. doi: 10.12461/PKU.DXHX202405072

    20. [20]

      Xueting Cao Shuangshuang Cha Ming Gong . 电催化反应中的界面双电层:理论、表征与应用. Acta Physico-Chimica Sinica, 2025, 41(5): 100041-. doi: 10.1016/j.actphy.2024.100041

Metrics
  • PDF Downloads(0)
  • Abstract views(993)
  • HTML views(190)

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

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return