Tetrahedron
Tetrahedron
5 years ago

Synthesis of novel naphtho[2,3-b]furan-4,9-diones bearing 2-aminopyridine moiety under aerobic condition and their absorption behaviors

Synthesis of novel naphtho[2,3-b]furan-4,9-diones bearing 2-aminopyridine moiety under aerobic condition and their absorption behaviors
We have developed an unprecedented base-promoted oxidative coupling of 2-hydroxy-1,4-naphthoquinones with (Z)-2-ylideneimidazo[1,2-a]pyridin-3(2H)-ones, which provide a convenient approach to access novel naphtho[2,3-b]furan-4,9-dione derivatives with a 2-aminopyridine moiety in acceptable yields under mild reaction conditions. These naphtho[2,3-b]furan-4,9-dione derivatives in ethanol showed the characteristic intense charge-transfer bands (π-π* transitions) occurring in the visible region. The p-substitutions of the phenyl group produced obviously effects on the maximum absorption wavelengths of these naphtho[2,3-b]furan-4,9-dione derivatives via an intramolecular charge transfer (ICT) process. Interestingly, the selected model compound 9aa exhibited selective response to Hg2+ and Pd2+ via a chelate-binding module and can be developed as a sensitive chromogenic sensor for Hg2+ in the presence of a range of competing cations in aqueous media.

Publisher URL: www.sciencedirect.com/science

DOI: S004040201731089X

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