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 an...

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Veröffentlicht in:	Organic letters 2008-03, Vol.10 (5), p.757-760
Hauptverfasser:	Deiseroth, Hans-Jörg, Granzhan, Anton, Ihmels, Heiko, Schlosser, Marc, Tian, Maoqun
Format:	Artikel
Sprache:	eng
Schlagworte:	Acridines - chemistry Amines - chemistry Molecular Structure Quinolinium Compounds - chemical synthesis Quinolinium Compounds - chemistry Spectrometry, Fluorescence Stereoisomerism
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creator	Deiseroth, Hans-Jörg Granzhan, Anton Ihmels, Heiko Schlosser, Marc Tian, Maoqun
description	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.
doi_str_mv	10.1021/ol702792r
format	Article
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subjects	Acridines - chemistry Amines - chemistry Molecular Structure Quinolinium Compounds - chemical synthesis Quinolinium Compounds - chemistry Spectrometry, Fluorescence Stereoisomerism
title	Synthesis of 6-Amino-3,4-dihydroisoquinolinium Derivatives by Ring-Opening Reactions of Acridizinium Ions
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