SIOC English
有机化学
高级检索

有机化学 >

2012 , Vol. 32 >Issue 10: 1888 - 1893

DOI: https://doi.org/10.6023/cjoc1202201

研究论文

含1,2,4-三唑和1,3,4-噁二唑硫醚类化合物的合成及结构表征

  • 王海卫 ,
  • 朱文娟 ,
  • 于知冉 ,
  • 李静 ,
  • 董保东 ,
  • 廖新成
展开
  • 郑州大学化学与分子工程学院 郑州 450052

收稿日期: 2012-02-20

  修回日期: 2012-05-29

  网络出版日期: 2012-06-12

基金资助

国家自然科学基金(No. 21171149)资助项目.

收起

Synthesis and Structure Characterization of Sulfur Ethers Containing 1,2,4-Triazole and 1,3,4-Oxadiazole

  • Wang Haiwei ,
  • Zhu Wenjuan ,
  • Yu Zhiran ,
  • Li Jing ,
  • Dong Baodong ,
  • Liao Xincheng
Expand
  • College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450052

Received date: 2012-02-20

  Revised date: 2012-05-29

  Online published: 2012-06-12

Supported by

Project supported by the National Natural Science Foundation of China (No. 21171149).

Fold

摘要

在KOH溶液中, 芳甲酰肼(2)与CS2生成钾盐3; 然后3在水合肼作用下经过环化、取代、肼解得3-巯基-4-氨 基-5-苯基-4H-1,2,4-三唑-乙酸酰肼(6), 6再与CS2回流成环生成化合物5-(4-氨基-5-苯基-4H-1,2,4-三唑-3-硫烷基)-1,3,4-噁二唑-2-硫醇(7), 最后7与取代苄基氯反应得目标化合物A1～A6, 与芳基甲醛反应得终产物B1～B15. 目标化合物的结构均经1H NMR, 13C NMR, IR, MS或HRMS确证结构.

关键词： 1,2,4-三唑; 1,3,4-噁二唑; 硫醚

本文引用格式

王海卫 , 朱文娟 , 于知冉 , 李静 , 董保东 , 廖新成 . 含1,2,4-三唑和1,3,4-噁二唑硫醚类化合物的合成及结构表征[J]. 有机化学, 2012 , 32(10) : 1888 -1893 . DOI: 10.6023/cjoc1202201

Abstract

Compound 3 was prepared by reaction of benzohydrazide (2) with CS2 in the presence of KOH as solvent. This compound converted to (4-amino-5-phenyl-4H-1,2,4-triazol-3-ylsulfanyl)-acetic acid hydrazide (6) by the reactions of cyclization, substitution and hydrazinolysis in the presence of hydrazine hydrate. Then 5-(4-amino-5-phenyl-4H-1,2,4-triazol- 3-ylsulfanylmethyl)-1,3,4-oxadiazole-2-thiol (7) were obtained by a refluence of compound 6 with CS2. This intermediate reacted with several substituted-benzyl chloride to afford a series of new derivatives A1～A6; in the meantime, reacted with several substituted-benzaldehyde to afford a series of new derivatives B1～B15. The structures of new products were characterized by means of 1H NMR, 13C NMR, IR, MS or HRMS techniques.

Key words： 1,2,4-triazole; 1,3,4-oxadiazole; sulfur ether

参考文献

[1] Sun, Y. R.; Li, Y. P.; Liu, C. J.; Wang, J. D. Chin. J. Org. Chem. 2008, 28(1), 151 (in Chinese).

(孙燕荣, 李燕萍, 刘晨江, 王吉德, 有机化学, 2008, 28(1), 151.)

[2] Sun, W. L.; Li, Y. P.; Liu, C. J.; Li, H. L. Chin. J. Appl. Chem. 2009, 26(8), 894 (in Chinese).

(孙文理, 李燕萍, 刘晨江, 李海龙, 应用化学, 2009, 26(8), 894.)

[3] Hu, G. Q.; Dong, X. L.; Xie, S. Q.; Huang, W. L. Acta Pharm. Sin. 2008, 43(1), 50 (in Chinese).

(胡国强, 董秀丽, 谢松强, 黄文龙, 药学学报, 2008, 43(1),50.)

[4] Yang, G. F.; Yang, H. Z. Acta Chin. Sinica 2001, 59(4), 447 (in Chinese).

(杨光富, 杨华铮, 化学学报, 2001, 59(4), 447.)

[5] Joshi, S. D.; Vagdevi, H. M.; Vaidya, V. P.; Gadaginamath, G. S. Eur. J. Med. Chem. 2008, 43, 1989.

[6] Zhang, C. R.; Wang, L.; Ge, Y. L.; Ju, X. L. Chin. J. Org. Chem. 2007, 27, 1432 (in Chinese).

(张成仁, 王柳, 葛燕丽, 巨修练, 有机化学, 2007, 27, 1432.)

[7] Omar, F. A.; Mahfouz, N. M.; Rahman, M. A. Eur. J. Med. Chem. 1996, 31, 819.

[8] Zareef, M.; Iqbal, R.; Mirza, B.; Khan, K. M.; Manan, A.; Asim, F.; Khan, S. W. ARKIVOC 2008, (ii), 141.

[9] Salomao, D. J.; Andrea, M.; Carlota Oliveira, R. Y.; Kerly Fernanda, M. P.; Leoberto, C. T. Bioorg. Med. Chem. 2009, 17, 3028.

[10] Eweiss, N. F.; Bahajaj, A. A.; Elsherbini, E. A. J. Heterocycl. Chem. 1986, 23, 1451.

[11] Li, Y.; Liu, J.; Zhang, H. Q.; Yang, X. P.; Liu, Z. J. Bioorg. Med. Chem. Lett. 2006, 16, 2278.

[12] Prasanta, K. S.; Rajesh, S.; Priyabrata, P. Med. Chem. Res. 2010, 19, 127.

[13] Wu, X. L.; Zhu, C. F.; Lu, Z. D. Chin. J. Org. Chem. 2011, 31, 824 (in Chinese).

(武现丽, 朱春风, 吕志丹, 有机化学, 2011, 31, 824.)

Options
文章导航

/

〈 〉