2-Arylideneferroceno[e]cyclohexanones and related 3-aryl-3,3a,4,5-tetrahydroferroceno[g]indazoles: synthesis, NMR-, DFT- and x-ray analysis

Kiss, Kolos and Kocsis, Vasile-Ludovic and Holczbauer, Tamás and Czugler, Mátyás and Silaghi-Dumitrescu, Luminita and Csámpai, Antal (2013) 2-Arylideneferroceno[e]cyclohexanones and related 3-aryl-3,3a,4,5-tetrahydroferroceno[g]indazoles: synthesis, NMR-, DFT- and x-ray analysis. Journal of Organometallic Chemistry, 726. pp. 79-87. ISSN 0022-328X

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Abstract

A series of 2-arylmethylideneferroceno[e]cyclohexanone was prepared by base-catalysed condensation of ferroceno[b]cyclohexanone with a variety of aryl aldehydes including formylferrocene. The decreased reactivity of these novel chalcones towards nucleophic reagents was interpreted by the comparision of DFT reactivity indices calculated for a selection of appropriate models. The conversion of five representative chalcones into ferroceno[g]indazoles of potential biological interest could be achieved by thiosemicarbazide-mediated cyclisation catalysed by hydrochloric acid in ethanol at reflux. The relative configurations of the novel chalcones and ferrocenoindazoles with the elements of planar-, helical- and central chirality were established by NMR methods and single-crystal x-ray diffraction.

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