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An Expeditious One-Pot Synthesis of N-Substituted 6-Nitroindoles from Indolines

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Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Summary.

 This paper reports an one-pot method for the concomitant alkylation – oxidation (aromatization) of indolines, particularly effective to get easy access to N-alkyl-6-nitroindoles, which are useful platforms in medicinal chemistry. N-alkyl-6-nitroindoles are obtained in good yield (64–91%) by reaction at room temperature in non-degassed DMF of 6-nitroindoline, an alkyl halide, and NaH as base. The presence of NaH appears to be essential for a high yield conversion.

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Authors and Affiliations

  1. Institut de Chimie Pharmaceutique Albert Lespagnol, F-59006 Lille, France, , , , , , FR

    Guillaume Laconde, Patrick Depreux & Jean-Pierre Hénichart

  2. Laboratoire de Pharmacie Chimique, Faculté de Pharmacie, F-59006 Lille, France, , , , , , FR

    Pascal Carato & Pascal Berthelot

  3. Ecole de Pharmacie, Université Catholique de Louvain, B-1200, Bruxelles, Belgium, , , , , , BE

    Jacques H. Poupaert

Authors
  1. Guillaume Laconde
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  2. Pascal Carato
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  3. Jacques H. Poupaert
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  4. Pascal Berthelot
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  5. Patrick Depreux
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  6. Jean-Pierre Hénichart
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Additional information

Corresponding author. E-mail: pdepreux@phare.univ-lille2.fr

Received December 3, 2002; accepted December 9, 2002 Published online May 26, 2003

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Laconde, G., Carato, P., Poupaert, J. et al. An Expeditious One-Pot Synthesis of N-Substituted 6-Nitroindoles from Indolines. Monatshefte für Chemie 134, 1037–1043 (2003). https://doi.org/10.1007/s00706-003-0005-5

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  • DOI: https://doi.org/10.1007/s00706-003-0005-5

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