Synthesis and characterization of N(1)-(4-toluenesulfonyl)-N(1)- (9-anthracenemethyl)triamines.
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.
Wang
Chaojie
C
Department of Chemistry, University of Florida, Gainesville 32611, USA.
Abboud
Khalil A
KA
Phanstiel IV
Otto
O
D000166:Acridines / Q000737:chemistry*; D000873:Anthracenes / Q000737:chemistry*; D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D013095:Spermidine / Q000737:chemistry*
D000166:Acridines; D000873:Anthracenes; C034020:anthracene; D013095:Spermidine