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

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ID: 50300
2018
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Abstract
9-Arylbenzo[b]quinolizinium derivatives were prepared with base-free Suzuki–Miyaura coupling reactions between benzo[b]quinolizinium-9-trifluoroborate and selected benzenediazonium salts. In addition, the Sonogashira coupling reaction between 9-iodobenzo[b]quinolizinium and the arylalkyne derivatives yielded four novel 9-(arylethynyl)benzo[b]quinolizinium derivatives under relatively mild reaction conditions. The 9-(N,N-dimethylaminophenylethynyl)benzo[b]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[b]quinolizinium derivatives revealed a significant binding affinity of these compounds towards both DNA forms with binding constants of Kb = 0.2–2.2 × 105 M−1.
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bandaru2018synthesisbeilstein Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Siva Sankar Murthy Bandaru, Darinka Dzubiel, Heiko Ihmels, Mohebodin Karbasiyoun, Mohamed M. A. Mahmoud, Carola Schulzke
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Journal Beilstein journal of organic chemistry
Year 2018
DOI
DOI not found
URL
https://doi.org/10.3762/bjoc.14.161
Keywords
chemistry Organic Chemistry Biology (General) Science biochemistry

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