Directed Aminomethylation of Pyrrole, Indole, and Carbazole with N,N,N′,N′-Tetramethylmethanediamine

Catalytic aminomethylation of pyrrole and indole with N , N , N′ , N′ -tetramethylmethanediamine in the presence of 5 mol % of ZrOCl 2 ·8H 2 O proceeds selectively at the positions 2 , 5 of pyrrole and 1 , 3 of indole. Carbazole under the same conditions affords 3-formyl-9-aminomethyl derivative. The reaction in the presence of 5 mol % of K 2 CO 3 occurs as monoaminomethylation: for pyrrole at the position 2 , for indole at the position 3 , and for carbazole at the nitrogen atom of the substrate. Water-soluble 1,1′-(1 H -pyrrole-2,5-diyl)bis( N , N -dimethylmethanamine) exhibits a fungistatic activity with respect to phytopathogenic fungi Rhizoctonia solani .