Synthesis of 9-arylalkynyl- and 9-aryl-substituted benzo[ b ]quinolizinium derivatives by Palladium-mediated cross-coupling reactions

9-Arylbenzo[ ]quinolizinium derivatives were prepared with base-free Suzuki-Miyaura coupling reactions between benzo[ ]quinolizinium-9-trifluoroborate and selected benzenediazonium salts. In addition, the Sonogashira coupling reaction between 9-iodobenzo[ ]quinolizinium and the arylalkyne derivative...

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Bibliographic Details
Published in:Beilstein journal of organic chemistry 2018-07, Vol.14 (1), p.1871-1884
Main Authors: Bandaru, Siva Sankar Murthy, Dzubiel, Darinka, Ihmels, Heiko, Karbasiyoun, Mohebodin, Mahmoud, Mohamed M A, Schulzke, Carola
Format: Article
Language:English
Subjects:
Binding sites
Chemistry
Deoxyribonucleic acid
DNA
DNA ligands
fluorescence
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heterocycles
Ligands
Palladium
Pd-mediated couling reactions
pH effects
quinolizinium
Salts
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Summary:9-Arylbenzo[ ]quinolizinium derivatives were prepared with base-free Suzuki-Miyaura coupling reactions between benzo[ ]quinolizinium-9-trifluoroborate and selected benzenediazonium salts. In addition, the Sonogashira coupling reaction between 9-iodobenzo[ ]quinolizinium and the arylalkyne derivatives yielded four novel 9-(arylethynyl)benzo[ ]quinolizinium derivatives under relatively mild reaction conditions. The 9-( , -dimethylaminophenylethynyl)benzo[ ]quinolizinium is only very weakly emitting, but the emission intensity increases by a factor >200 upon protonation, so that this derivative may operate as pH-sensitive light-up probe. Photometric and fluorimetric titrations of duplex and quadruplex DNA to 9-(arylethynyl)benzo[ ]quinolizinium derivatives revealed a significant binding affinity of these compounds towards both DNA forms with binding constants of = 0.2-2.2 × 10 M .
ISSN:1860-5397
2195-951X
1860-5397
DOI:10.3762/bjoc.14.161