Synthesis of 6-amino-3,4-dihydroisoquinolinium derivatives by ring-opening reactions of acridizinium ions.
The 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.
Deiseroth
Hans-Jörg
HJ
Universität Siegen, Anorganische Chemie I, Adolf-Reichwein-Strasse 2, D-57068 Siegen, Germany.
Granzhan
Anton
A
Ihmels
Heiko
H
Schlosser
Marc
M
Tian
Maoqun
M
D000166:Acridines / Q000737:chemistry*; D000588:Amines / Q000737:chemistry; D015394:Molecular Structure; D011806:Quinolinium Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013050:Spectrometry, Fluorescence; D013237:Stereoisomerism
D000166:Acridines; D000588:Amines; D011806:Quinolinium Compounds