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Issue 14, 2005
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Isomeric [RuCl2(dmso)2(indazole)2] complexes: ruthenium(II)-mediated coupling reaction of acetonitrile with 1H-indazole

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Reaction of the antitumor complex trans-[RuIIICl4(Hind)2] (Hind = indazole) with an excess of dimethyl sulfoxide (dmso) in acetone afforded the complex trans,trans,trans-[RuIICl2(dmso)2(Hind)2] (1). Two other isomeric compounds trans,cis,cis-[RuIICl2(dmso)2(Hind)2] (2) and cis,cis,cis-[RuIICl2(dmso)2(Hind)2] (3) have been obtained on refluxing cis-[RuIICl2(dmso)4] with 2 equiv. of indazole in ethanol and methanol, respectively. Isomers 1 and 2 react with acetonitrile yielding the complexes trans-[RuIICl2(dmso)(Hind){HN[double bond, length as m-dash]C(Me)ind}]·CH3CN (4·CH3CN) and trans,cis-[RuIICl2(dmso)2{HN[double bond, length as m-dash]C(Me)ind}]·H2O (5·H2O), respectively, containing a cyclic amidine ligand resulting from insertion of the acetonitrile C[triple bond, length as m-dash]N group in the N1–H bond of the N2-coordinated indazole ligand in the nomenclature used for 1H-indazole. These are the first examples of the metal-assisted iminoacylation of indazole. The products isolated have been characterized by elemental analysis, IR spectroscopy, UV-vis spectroscopy, electrospray mass-spectrometry, thermogravimetry, differential scanning calorimetry, 1H NMR spectroscopy, and solid-state 13C CP MAS NMR spectroscopy. The isomeric structures of 1–3 and the presence of a chelating amidine ligand in 4 and 5 have been confirmed by X-ray crystallography. The electrochemical behavior of 1–5 and the formation of 5 have been studied by cyclic voltammetry.

Graphical abstract: Isomeric [RuCl2(dmso)2(indazole)2] complexes: ruthenium(ii)-mediated coupling reaction of acetonitrile with 1H-indazole

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Publication details

The article was received on 11 Mar 2005, accepted on 03 Jun 2005 and first published on 15 Jun 2005

Article type: Paper
DOI: 10.1039/B503650J
Citation: Dalton Trans., 2005,0, 2355-2364
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    Isomeric [RuCl2(dmso)2(indazole)2] complexes: ruthenium(II)-mediated coupling reaction of acetonitrile with 1H-indazole

    E. Reisner, V. B. Arion, A. Rufińska, I. Chiorescu, W. F. Schmid and B. K. Keppler, Dalton Trans., 2005, 0, 2355
    DOI: 10.1039/B503650J

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