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  • Title: Synthesis of 6-amino-3,4-dihydroisoquinolinium derivatives by ring-opening reactions of acridizinium ions.
    Author: Deiseroth HJ, Granzhan A, Ihmels H, Schlosser M, Tian M.
    Journal: Org Lett; 2008 Mar 06; 10(5):757-60. PubMed ID: 18232697.
    Abstract:
    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.
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