Furan derivatives—III : Synthesis and properties of β-ketosulphides and sulphur derivatives of chalcones of 5-nitrofuran series |
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Authors: | A. Jurášek V. Knoppová M. Dandárová J. Kováč L. Reinprecht |
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Affiliation: | Department of Organic Chemistry, Slovak Technical University, Bratislava, Czechoslovakia |
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Abstract: | A series of 2-(5-nitro-2-furyl)-2-oxoethylarylsulphides 3a–3h has been prepared by the reaction of 5-nitro-2-furylbromomethylketone 1 with 4-substituted thiophenols 2a–2h. The determined rates of carbanion formation (log k'), pK values as well as 1H NMR data show that in these compounds transmission of polar effects by the substituents through the -S- group occurs. Compounds 3a–3h react with aromatic aldehydes affording sulphur chalcone derivativěs of the 5-nitrofuran series 4a–4h. 1H NMR, IR and UV spectra of prepared compounds are discussed. |
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