Synthesis of 9-arylalkynyl- and 9-aryl-substituted Benzo[]quinolizinium Derivatives by Palladium-mediated Cross-coupling Reactions

Overview

Journal Beilstein J Org Chem

Specialty Chemistry

Date 2018 Aug 17

PMID 30112092

Authors

Siva Sankar Murthy Bandaru

Darinka Dzubiel

Heiko Ihmels

Mohebodin Karbasiyoun

Mohamed M A Mahmoud

Carola Schulzke

Affiliations

Soon will be listed here.

Abstract

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.

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