Synthesis and characterization of N-1-(4-toluenesulfonyl)-N-1-(9-anthracenemethyl)triamines
Abbreviated Journal Title
J. Org. Chem.
TRANSPORT; HOMOLOGATION; SPERMINE; ANALOGS; Chemistry, Organic
A modular synthetic approach was developed to access triamines with varying tether lengths from commercially available aminoalkanols. Initial N-alkylation via reductive amination with anthracene-9-carbaldehyde provided the secondary amines in good yield. Subsequent ditosylation with excess TsCl yielded the respective bis-N,O-tosylates. The tosylates were reacted with excess putrescine to give the final triamines. X-ray crystallography revealed that the polyamine tail is preferentially oriented over the shielding cone of the anthracene ring.
Journal of Organic Chemistry
"Synthesis and characterization of N-1-(4-toluenesulfonyl)-N-1-(9-anthracenemethyl)triamines" (2002). Faculty Bibliography 2000s. 3529.