Citation: 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 shu

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

Department of Chemistry, Capital Normal University, Beijing 100048

Corresponding author: Wang Jianchun, cnuwjc@cnu.edu.cn
Received Date: 25 November 2016
Revised Date: 9 February 2017

Fund Project: the General Plan of Beijing Municipal Education Commission KM201710028007the Beijing Natural Science Foundation 2173060

Figures(5)

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.
- ferrocene,
- thiazole,
- imidazole,
- iron(Ⅲ) ion recognition,
- tautomerism
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Synthesis of Novel Ferrocenyl Thiazole and Imidazole Derivatives and Its Selective Recognition to Fe3+

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