期刊
NEW JOURNAL OF CHEMISTRY
卷 37, 期 7, 页码 2019-2030出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c3nj00182b
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资金
- Ministry of Education, Youth and Sports of the Czech Republic [MSM0021620857]
- National Grid Infrastructure MetaCentrum [LM2010005]
- CERIT-SC [CZ.1.05/3.2.00/08.0144]
2-Ferrocenyl-4(3H)-quinazolinone (2) was obtained by acylation of 2-aminobenzoic amide with ferrocenecarbonyl chloride (FcCOCl) and subsequent base-catalysed cyclisation of the intermediate 2-(ferrocenecarboxamido) benzamide (1). The related benzoxazin-4-one (4) was obtained analogously (though in one step) from FcCOCl and 2-aminobenzoic acid. Compounds 2 and 4 were thionated with P2S5 to give the corresponding ferrocenylated 4(3H)-quinazoline thione (3), and a mixture of benzothiazine-4-thione (5) and benzothiazine-4-one (6, major), respectively. Attempts to prepare 3-amino-2-ferrocenyl-4(3H)-quinazolinone from 4 and hydrazine hydrate failed. The reaction gave only 2-(ferrocenecarboxamido) benzohydrazide (7), which reacted with 2-chloro-1,3-dimethylimidazolidinium chloride to afford a mixture of cyclic and open (major) condensation products, both bearing the 1,3-dimethylimidazolidin-2-ylidene terminal group (8 and 9). All compounds were characterised by spectroscopic methods and the molecular structures of 1-7 and 9 were determined by X-ray diffraction analysis. Cyclic voltammetric measurements revealed that the compounds undergo a single one-electron oxidation, localised presumably at the ferrocene unit. DFT computations for 2 as a representative example performed in the gas phase and crystal state, reproduced well the experimental geometry and further supported the assignment of the redox processes.
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