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.

9-氟吖啶鎓（9-氟苯并[b]喹嗪鎓）或9-氨基吖啶鎓（9-氨基苯并[b]喹嗪鎓）离子与伯烷基胺的反应，可通过高非对映选择性生成6-氨基-3,4-二氢异喹啉鎓衍生物作为主要产物，该类衍生物具有显著的吸收与荧光特性。据推测，该反应经由亲核开环步骤后发生氮杂狄尔斯-阿尔德（aza Diels−Alder）反应进行。