Bibliographic Information

An Expeditious One-Pot Synthesis of N-Substituted 6-Nitroindoles from Indolines.     Laconde, Guillaume; Carato, Pascal; Poupaert, Jacques H.; Berthelot, Pascal; Depreux, Patrick; Henichart, Jean-Pierre.    Institut de Chimie Pharmaceutique Albert Lespagnol,  Lille,  Fr.    Monatshefte fuer Chemie  (2003),  134(7),  1037-1043.  CODEN: MOCMB7  ISSN: 0026-9247.  Journal  written in English.    CAN 140:93872    AN 2003:449208    CAPLUS  

Abstract

This paper reports an one-pot method for the concomitant alkylation - oxidn. (aromatization) of indolines, particularly effective to get easy access to N-alkyl-6-nitroindoles, which are useful platforms in medicinal chem.  N-alkyl-6-nitroindoles are obtained in good yield (64-91%) by reaction at room temp. 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.  

Indexing -- Section 27-11  (Heterocyclic Compounds (One Hetero Atom)