TRANSITION METAL-CATALYZED C,C- AND C,N-CYCLOAMINOMETHYLATION REACTIONS OF PYRROLE AND INDOLE

Abstract

Catalytic cycloaminomethylation of pyrrole with bis(methoxymethyl)alkylamines or a mixture of alkyl(phenyl)amines and paraformaldehyde in the presence of [Ni(Py)₄Cl₂]·0.76H₂O or NiCl₂·6H₂O catalysts proceeded at positions 2 and 5 of pyrrole ring. Cycloaminomethylation of indole was accomplished effectively at positions 1 and 3 in the presence of ZrOCl₂·8H₂O catalyst. When carbazole was treated with bis(methoxymethyl)alkylamine in the presence of ZrOCl₂·8H₂O catalyst, it was converted to N-aminomethylated product – N-[(9H-carbazol-9-yl)methyl]-N-(methoxymethyl)alkylamine.