An Expeditious One-Pot Synthesis of N-Substituted 6-Nitroindoles from Indolines |
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| Authors: | Guillaume Laconde Pascal Carato Jacques H Poupaert Pascal Berthelot Patrick Depreux Jean-Pierre Hénichart |
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| Institution: | (1) Institut de Chimie Pharmaceutique Albert Lespagnol, F-59006 Lille, France, FR;(2) Laboratoire de Pharmacie Chimique, Faculté de Pharmacie, F-59006 Lille, France, FR;(3) Ecole de Pharmacie, Université Catholique de Louvain, B-1200, Bruxelles, Belgium, BE |
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| Abstract: | 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.
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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| Keywords: | , Heterocycles, Indole, Indoline, Oxydation, Aromatization, |
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