Synthesis of Axially Chiral Cationic Benzo[c]phenanthridinium Derivatives - Aix-Marseille Université Access content directly
Journal Articles Synthesis: Journal of Synthetic Organic Chemistry Year : 2022

Synthesis of Axially Chiral Cationic Benzo[c]phenanthridinium Derivatives

Abstract

Cationic polycyclic aromatic compounds containing one or more nitrogen atom(s), also known as azonia polycyclic aromatic compounds, form a valuable class of molecules because of their fluorescent and/or medicinal properties. N-Arylated hydroisoquinoline derivatives were synthesized through an aryne aza-Diels–Alder cycloaddition/N-arylation sequence. A subsequent two-electron oxidation allowed the synthesis of some axially chiral cationic benzo[c]phenanthridinium derivatives. The structural and optical properties of some of these molecules were determined. Their chirality was evidenced experimentally by single-crystal X-ray diffraction and 1H NMR spectroscopy, and their conformational behavior was examined by computational DFT methods.
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Dates and versions

hal-03856921 , version 1 (17-11-2022)

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Cite

Brian Castro Agudelo, Florian Rigoulet, Michel Giorgi, Babak Sayah, Jean Rodriguez, et al.. Synthesis of Axially Chiral Cationic Benzo[c]phenanthridinium Derivatives. Synthesis: Journal of Synthetic Organic Chemistry, 2022, 54 (22), pp.5035-5041. ⟨10.1055/a-1845-3128⟩. ⟨hal-03856921⟩

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