Synthetic applications of aryl radical building blocks for cyclisation onto azoles

Steven M. Allin, W. Russell Bowman, Mark R.j. Elsegood, Vickie Mckee, Rehana Karim, Shahzad S. Rahman

    Allbwn ymchwil: Cyfraniad at gyfnodolynErthygladolygiad gan gymheiriaid

    Crynodeb

    2-(2-Bromophenyl)ethyl groups have been used as building blocks in radical cyclisation reactions onto azoles to synthesise tri- and tetra-cyclic heterocycles. 2-(2-Bromophenyl)ethyl methanesulfonate was used to alkylate azoles (imidazoles, pyrroles, indoles and pyrazoles) for the synthesis of the radical precursors. Cyclisations of the intermediate aryl radicals yield new 6-membered rings attached to the azoles. The aryl radicals undergo intramolecular homolytic aromatic substitution onto the azole rings. Tributylgermanium hydride has been used with success to replace the toxic and troublesome tributyltin hydride. Initial studies show that the protocol can be used on solid phase resins. The molecular and crystal structures of methyl 5,6-dihydroimidazo[5,1-a]iso-quinoline-1-carboxylate and methyl 5,6-dihydroimidazo[2,1-a]isoquinoline-3-carboxylate were determined by X-ray crystallography.

    2-(2-Bromophenyl)ethyl groups have been used as building blocks in radical cyclisation reactions to synthesis tri- and tetra-cyclic heterocycles.

    Iaith wreiddiolSaesneg
    Tudalennau (o-i)2689-2696
    CyfnodolynTetrahedron Letters
    Cyfrol61
    Rhif cyhoeddi10
    Dynodwyr Gwrthrych Digidol (DOIs)
    StatwsCyhoeddwyd - 1 Maw 2005

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