A Photochemical Route to Benzo[a]carbazoles via Domino Elimination/Electrocyclization of 2-Aryl-3-(1-tosylalkyl)indoles

Authors

  • Stefano Protti,

    Corresponding author
    1. PhotoGreen Lab, Department of Chemistry, University of Pavia, V. Le Taramelli 12, 27100 Pavia, Italy, Fax: (+39)-038-298-7323; phone: (+39)-038-298-7316
    • PhotoGreen Lab, Department of Chemistry, University of Pavia, V. Le Taramelli 12, 27100 Pavia, Italy, Fax: (+39)-038-298-7323; phone: (+39)-038-298-7316
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  • Alessandro Palmieri,

    Corresponding author
    1. Green Chemistry Group, School of Science and Technology, Chemistry Division, University of Camerino, Via S. Agostino 1, 62032 Camerino (MC), Italy
    • Green Chemistry Group, School of Science and Technology, Chemistry Division, University of Camerino, Via S. Agostino 1, 62032 Camerino (MC), Italy
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  • Marino Petrini,

    1. Green Chemistry Group, School of Science and Technology, Chemistry Division, University of Camerino, Via S. Agostino 1, 62032 Camerino (MC), Italy
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  • Maurizio Fagnoni,

    1. PhotoGreen Lab, Department of Chemistry, University of Pavia, V. Le Taramelli 12, 27100 Pavia, Italy, Fax: (+39)-038-298-7323; phone: (+39)-038-298-7316
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  • Roberto Ballini,

    1. Green Chemistry Group, School of Science and Technology, Chemistry Division, University of Camerino, Via S. Agostino 1, 62032 Camerino (MC), Italy
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  • Angelo Albini

    1. PhotoGreen Lab, Department of Chemistry, University of Pavia, V. Le Taramelli 12, 27100 Pavia, Italy, Fax: (+39)-038-298-7323; phone: (+39)-038-298-7316
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Abstract

The photochemical synthesis of benzo[a]carbazoles from easily synthesizable 2-aryl-3-(1-tosylalkyl)indoles is presented. Irradiation of these substrates in polar aprotic solvents (acetone or THF) gives selectively the target products in satisfactory yields. This versatile and efficient procedure promises to be a useful alternative to the multistep strategies reported in the literature.

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