ol702792r_si_003.cif (24.83 kB)
Synthesis of 6-Amino-3,4-dihydroisoquinolinium Derivatives by Ring-Opening Reactions of Acridizinium Ions
dataset
posted on 2008-03-06, 00:00 authored by Hans-Jörg Deiseroth, Anton Granzhan, Heiko Ihmels, Marc Schlosser, Maoqun TianThe reaction of the 9-fluoroacridizinium (9-fluorobenzo[b]quinolizinium) or the 9-aminoacridizinium (9-aminobenzo[b]quinolizinium) ion with
primary alkyl amines gives with high diastereoselectivity 6-amino-3,4-dihydroisoquinolinium derivatives as main products, which exhibit
pronounced absorption and fluorescence properties. It is proposed that the reaction proceeds via a nucleophilic ring-opening followed by an
aza Diels−Alder reaction.