INDOLES FROM 2-METHYLNITROBENZENES BY CONDENSATION WITH FORMAMIDE ACETALS FOLLOWED BY REDUCTION: 4-BENZYLOXYINDOLE

Indoles from 2-Methylnitrobenzenes by Condensation with Formamide Acetals Followed by Reduction: 4-Benzyloxyindole intermediate: 6-benzyloxy-2-nitrotoluene intermediate: (E)-6-benzyloxy-2-nitro-β-pyrrolidinostyrene and (E)-6-benzyloxy-β-dimethylamino-2-nitrostyrene product: 4-benzyloxyindole intermediate: pyrrolidine enamine, mp 108–110° (MeOH), and N,N-dimethylenamine Keywords: alkenylation, C-alkenylation; alkylation, O-alkylation; aminomethylenation; annulation, heterocyclic-[5]; cyclization, reductive cyclization; reduction, miscellaneous

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