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Orthogonal Synthesis of Fluorinated Acridones and Acridines from Perfluorobenzophenone

  1. Paola Del Buttero2,
  2. Ramona Gironda1,
  3. Massimo Moret1,
  4. Antonio Papagni1,
  5. Matteo Parravicini1,
  6. Silvia Rizzato3,
  7. Luciano Miozzo1,4

Article first published online: 2 MAR 2011

DOI: 10.1002/ejoc.201001647

Issue

European Journal of Organic Chemistry

European Journal of Organic Chemistry

Volume 2011, Issue 12, pages 2265–2271, April 2011

Additional Information

How to Cite

Del Buttero, P., Gironda, R., Moret, M., Papagni, A., Parravicini, M., Rizzato, S. and Miozzo, L. (2011), Orthogonal Synthesis of Fluorinated Acridones and Acridines from Perfluorobenzophenone. Eur. J. Org. Chem., 2011: 2265–2271. doi: 10.1002/ejoc.201001647

Author Information

  1. 1

    Dipartimento di Scienza dei Materiali, Università di Milano Bicocca, Via R.Cozzi, 53 Milano, Italy, Fax: +39-0264485400

  2. 2

    Dipartimento di Chimica Organica e Industriale, Università degli Studi di Milano, Via Venezian, 21 Milano, Italy

  3. 3

    Dipartimento di Chimica Strutturale e Stereochimica Inorganica and Facoltà di Farmacia, Università degli Studi di Milano, Via Venezian, 21Milano, Italy

  4. 4

    ITODYS, Université Paris Diderot, 15, Jean Antoine de Baïf, 75205 Paris, France

Publication History

  1. Issue published online: 5 APR 2011
  2. Article first published online: 2 MAR 2011
  3. Manuscript Received: 8 DEC 2010

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Keywords:

  • Nucleophilic substitution;
  • ­Pericyclic reactions;
  • Fluorine;
  • Nitrogen heterocycles;
  • Solvent effects

Abstract

The reaction between perfluorobenzophenone and aromatic amines proceeds with the substitution of one or more fluorine atoms. The regiochemistry of this substitution is controlled by solvent polarity, temperature, and nucleophilic character of the amine. o-Anilinononafluorobenzophenone can be selectively transformed into acridines or acridones by using acid or base catalysis through electrocyclization or aromatic nucleophilic substitution.

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