552318-11-3Relevant academic research and scientific papers
Novel heterocyclic Tro?ger's base derivatives containing N-methylpyrrole units
Valík, Martin,Dolensky, Bohumil,Pet?í?ková, Hana,Va?ek, Petr,Král, Vladimír
, p. 2083 - 2086 (2003)
Novel analogues of Tr?ger's base were prepared regioselectively from 4-amino-N-methylpyrrole carboxylates in good yield. Catalytic hydrogenation of dibenzyl-4,9-methano-1,6-dimethyl-4,5,9,10-tetrahydro-1H,6H-dipyrrolo- [3,2-b:3′,2′-f][1,5]diazocin-2,7-dicarboxylate 2b led to 4,9-methano-1,6-dimethyl-4,5,9,10-tetrahydro-1H,6H-dipyrrolo-[3,2-b: 3′,2′-f][1,5]diazocin-2,7-dicarboxylic acid 3 which was used for the preparation of Tr?ger's base derivatives of natural antibiotics via an amide protocol. The novel heterocyclic Tr?ger's bases were characterized by a variety of spectroscopic techniques and compound 2b by X-ray crystallography. Incorporation of guanidine as the terminal group in the N-methylpyrrole Tr?ger's base skeleton opens the possibility for preparation of water soluble derivatives.
