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2012 >Issue 03: 612 - 615

DOI: https://doi.org/10.6023/cjoc1108072

研究简报

无溶剂条件下简单、有效地合成1,6-二氢嘧啶-6-酮衍生物

  • 刘丽华 ,
  • 殷姗 ,
  • 夏盛 ,
  • 蔡佩君 ,
  • 荣良策
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  • a 中国矿业大学化工学院 徐州 221008;
    b 徐州师范大学化学化工学院 徐州 221116

收稿日期: 2011-08-07

  修回日期: 2011-10-22

  网络出版日期: 2012-03-24

基金资助

江苏省高校自然科学基础研究基金(No. 08KJB150017)及徐州师范大学科研平台(No. 10XLS02)资助项目.

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A Facile and Efficient Synthesis of 1,6-Dihydro-6-oxo-pyrimidine Derivatives under Solvent-Free Conditions

  • Liu Lihua ,
  • Yin Shan ,
  • Xia Sheng ,
  • Cai Peijun ,
  • Rong Liangce
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  • a School of Chemical Engineering and Technology, China University of Mining and Technology, Xuzhou 221008;
    b College of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou 221116

Received date: 2011-08-07

  Revised date: 2011-10-22

  Online published: 2012-03-24

Supported by

Project supported by the Natural Science Foundation of Jiangsu Education Department (No. 08KJB150017) and the Research Platform Foundation of Xuzhou Normal University (No. 10XLS02).

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摘要

以芳醛、氰乙酸乙酯和碳酸胍为原料, 氢氧化钠-碳酸钾为催化剂, 在无溶剂条件下70 ℃反应有效地合成了1,6-二氢嘧啶-6-酮衍生物, 本方法具有反应时间短、条件温和、处理简单和环境友好等优点. 通过红外、核磁、高分辨质谱和晶体的X 衍射确定产物的结构.

关键词： 1,6-二氢-6-嘧啶酮; 杂环化合物; 无溶剂反应

本文引用格式

刘丽华 , 殷姗 , 夏盛 , 蔡佩君 , 荣良策 . 无溶剂条件下简单、有效地合成1,6-二氢嘧啶-6-酮衍生物[J]. 有机化学, 2012 , (03) : 612 -615 . DOI: 10.6023/cjoc1108072

Abstract

An efficient and facile synthesis of 2-amino-1,6-dihydro-6-oxo-pyrimidine derivatives via reaction of aromatic aldehydes, ethyl 2-cyanoacetate and guanidine carbonate by using NaOH and K2CO3 as catalyst under solvent-free conditions at about 70 ℃ is reported. This protocol has the advantages of shorter time, mild conditions, easy work-up and environmental friendliness. The products were identified by IR, 1H NMR and HRMS techniques, and that of 4e was additionally confirmed by X-ray diffraction analysis.

Key words： 6-oxo-pyrimidine; heterocyclic compound; solvent-free reaction

参考文献

[1] Regnier, G.; Canevari, R.; Le Douarec, J.; Holstorp, S.; Daussy, J.J. Med. Chem. 1972, 15, 295.  

[2] Suguira, K.; Schmid, A. F.; Schmid, M. M.; Brown, F. G. CancerChemother. Rep. Part 2 1973, 3, 231.

[3] Otzen, T.; Wempe, E. G.; Kunz, B.; Bartels, R.; Lehwark-Yvetot,G.; Hänsel, W.; Schaper, K. J.; Seydel, J. K. J. Med. Chem. 2004,47, 240.  

[4] Wen, R. Organic Reactions for Drug Synthesis, Chemical IndustryPress, Beijing, 2001, pp. 64～72 (in Chinese).(闻韧, 药物合成反应, 化学工业出版社, 北京, 2001, pp. 64～72.)  

[5] Kappe, C. O. Eur. J. Med. Chem. 2000, 35, 1043.

[6] Snider, B. B.; Shi, Z. P. J. Org. Chem. 1993, 58, 3828.  

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

[8] Yu Y.; Guo, H. Y. Chin. J. Org. Chem. 2011, 31, 96 (in Chinese).(余意, 郭红云, 有机化学, 2011, 31, 96.)

[9] Zhuang, Q. Y.; Fu, Y. C.; Tang, D.; Zha, Y. Y.; Rong, L. C.; Tu, S.J. Chin. J. Org. Chem. 2010, 30, 1405 (in Chinese).(庄启亚, 付永春, 唐丹, 査云赟, 荣良策, 屠树江, 有机化学,2010, 30, 1405.)

[10] Deshmukh, M. B.; Salunkhe, S. M.; Patil, D. R.; Anbhule, P. V.Eur. J. Med. Chem. 2009, 44, 2651.

[11] Bararjanian, M.; Balalaie, S.; Rominger, F.; Rarouti, S. Helv. Chim.Acta 2010, 93, 777.  

[12] Sheibani, H.; Seifi, M.; Bazgir, A. Synth. Commun. 2009, 39, 1055.  
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