An expeditious one-pot synthesis of N-substituted 6-nitroindoles from indolines

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