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Chinese Journal of Organic Chemistry >

2017 , Vol. 37 >Issue 6: 1412 - 1416

DOI: https://doi.org/10.6023/cjoc201611037

ARTICLE

Synthesis of Novel Ferrocenyl Thiazole and Imidazole Derivatives and Its Selective Recognition to Fe3＋

  • Wu Xiaofang ,
  • Wu Pei ,
  • Li Jingyu ,
  • Lu Jing ,
  • Wang Jianchun
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  • Department of Chemistry, Capital Normal University, Beijing 100048

Received date: 2016-11-25

  Revised date: 2017-02-09

  Online published: 2017-02-27

Supported by

Project supported by the Beijing Natural Science Foundation (No. 2173060) and the General Plan of Beijing Municipal Education Commission (No. KM201710028007).

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Abstract

Five novel ferrocenyl thiazole and imidazole derivatives were synthesized. The structure characterization of the five products showed that ferrocene conjugative unit and thiazole or imidazole conjugative unit were linked by carbonyl methylene skeleton (COCH2). Chloroacetylferrocene (1a) was prepared by chloroacetylation of ferrocene which reacted with different heterocyclic compounds (2-mercaptobenzothiazole, 2-mercaptobenzimidazole, imidazole and benzimidazole) to give four novel compounds, respectively. 1,1'-Bis(bromoacetyl)ferrocene (1b) was prepared by acetylation and subsequent bromination of ferrocene, which then reacted with 2-mercaptobenzothiazole to produce 2e. All the new compounds were confirmed by 1H NMR, 13C NMR, ESI-MS, HRMS and IR. Three single crystal structures were obtained. Recognition properties on 14 metal ions of the five new compounds were investigated by UV-vis spectrum. The results showed that the five new compounds possessed recognition properties only to iron(III), in which 2a had maximum spectra response.

Key words： ferrocene; thiazole; imidazole; iron(III) ion recognition; tautomerism

Cite this article

Wu Xiaofang , Wu Pei , Li Jingyu , Lu Jing , Wang Jianchun . Synthesis of Novel Ferrocenyl Thiazole and Imidazole Derivatives and Its Selective Recognition to Fe3＋[J]. Chinese Journal of Organic Chemistry, 2017 , 37(6) : 1412 -1416 . DOI: 10.6023/cjoc201611037

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