title: Synthesis and characterization of N(1)-(4-toluenesulfonyl)-N(1)- (9-anthracenemethyl)triamines.
abstract: 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.
authors.affiliation: Department of Chemistry, University of Florida, Gainesville 32611, USA.
authors.forename: Chaojie
authors.initials: C
authors.lastname: Wang
authors.forename: Khalil A
authors.initials: KA
authors.lastname: Abboud
authors.forename: Otto
authors.initials: O
authors.lastname: Phanstiel IV
mesh_terms: 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*
chemical_list: D000166:Acridines; D000873:Anthracenes; C034020:anthracene; D013095:Spermidine