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Stachel, Hans‐Dietrich; Immerz‐Winkler, Elisabeth; Poschenrieder, Hermann; Windt, Andreas; Weigand, Wolfgang; Drescher, Norbert; Wünsch, Ralf

Metal Complexes of Functionalized Sulfur‐Containing Ligands. Part XIX : Synthesis and Reactions of New Pyrroloisothiazoles : Synthesis and Reactions of New Pyrroloisothiazoles

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  • Medientyp: E-Artikel
  • Titel: Metal Complexes of Functionalized Sulfur‐Containing Ligands. Part XIX : Synthesis and Reactions of New Pyrroloisothiazoles : Synthesis and Reactions of New Pyrroloisothiazoles
  • Beteiligte: Stachel, Hans‐Dietrich; Immerz‐Winkler, Elisabeth; Poschenrieder, Hermann; Windt, Andreas; Weigand, Wolfgang; Drescher, Norbert; Wünsch, Ralf
  • Erschienen: Wiley, 2003
  • Erschienen in: Helvetica Chimica Acta
  • Sprache: Englisch
  • DOI: 10.1002/hlca.200390200
  • ISSN: 0018-019X; 1522-2675
  • Schlagwörter: Inorganic Chemistry ; Organic Chemistry ; Physical and Theoretical Chemistry ; Drug Discovery ; Biochemistry ; Catalysis
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  • Beschreibung: <jats:title>Abstract</jats:title><jats:p>The title compounds were prepared starting from the dihydropyrrolones <jats:bold>4</jats:bold>–<jats:bold>6</jats:bold>. Nucleophilic displacement and ring closure yielded the 1<jats:italic>H</jats:italic>‐pyrrolo[3,2‐<jats:italic>c</jats:italic>]isothiazol‐5(4<jats:italic>H</jats:italic>)‐ones <jats:bold>8</jats:bold> and <jats:bold>10</jats:bold>. The fused systems formed salts with strong acids and electrophiles (<jats:bold>15, 16</jats:bold>), as well as with bases. Oxidation led either to <jats:italic>S</jats:italic>(2)‐oxides (<jats:bold>18a, 20a</jats:bold>) or to the corresponding bicyclic sultams (<jats:bold>18b, 20b</jats:bold>), depending on the reaction conditions. The sulfinamide <jats:bold>18a</jats:bold> was also obtained from the known 1,2‐dithiolopyrrolone <jats:italic>S</jats:italic>‐oxide <jats:bold>21</jats:bold> by a ring‐opening/ring‐closure reaction sequence. <jats:italic>O</jats:italic>‐Methylation of <jats:bold>8</jats:bold> furnished the ‘azafulvene' <jats:bold>17</jats:bold>. The oxidative addition of [Pt(<jats:italic>η</jats:italic><jats:sup>2</jats:sup>‐C<jats:sub>2</jats:sub>H<jats:sub>4</jats:sub>)L<jats:sub>2</jats:sub>] (<jats:bold>24a</jats:bold>: L=Ph<jats:sub>3</jats:sub>P, <jats:bold>24b</jats:bold>: L=1/2 dppf, <jats:bold>24c</jats:bold>: L=1/2 (<jats:italic>R</jats:italic>,<jats:italic>R</jats:italic>)‐diop) to <jats:bold>18a</jats:bold> and <jats:bold>20a</jats:bold> led to the <jats:italic>cis</jats:italic>‐amido‐sulfenato Pt complexes <jats:bold>25</jats:bold> and <jats:bold>26a</jats:bold>–<jats:bold>c</jats:bold>, respectively.</jats:p>