

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.
Keywords
bis(methoxymethyl)alkylamines; carbazole; indole; Lewis acids; pyrrole; catalysis; cycloaminomethylation; fungicides; heterocyclization
Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv