Switching between ring closed and open N-incorporated heterocycles with tuneable charges and modular reactivity based upon 5-(2-bromoethyl)phenanthridinium bromide.
5-(2-bromoethyl)phenanthridinium bromide (BEP) undergoes a 3-step-one-pot cyclisation reaction with primary amines allowing the facile synthesis of a vast library of heterocycles. A diverse range of primary aryl amines were explored as reactants to gain insight into the product isolated as a result of the steric and electronic effects of the aryl precursors. Analysis and reaction monitoring with UV-vis and NMR spectroscopy revealed that excessively electron withdrawing groups and sterically hindered amines do not allow for isolation of the common neutral tetrahydroimidazophenanthridine (TIP) structure but allow either the isolation of the charged dihydroimadazophenanthridinium (DIP) or aminoethylphenanthridinium (AEP) products.
WestCHEM, School of Chemistry, University of Glasgow, Glasgow, United Kingdom.
Roslyn
R
Eadie
Craig
C
Richmond
Samantha
S
Moreton
Leroy
L
Cronin
D000588:Amines / Q000138:chemical synthesis / Q000737:chemistry*; D001965:Bromides / Q000138:chemical synthesis / Q000737:chemistry*; D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy; D010617:Phenanthridines / Q000138:chemical synthesis / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet
D000588:Amines; D001965:Bromides; D010617:Phenanthridines; C014740:phenanthridinium