Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 17, Issue -, Pages 719-729Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.17.61
Keywords
dibenzosuberenone; inverse electron-demand Diels-Alder cycloaddition reactions; p-quinone methide; polycyclic pi-conjugated dihydropyridazines; pyridazines; pyrroles
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Funding
- Scientific and Technological Research Council of Turkey (TUBITAK) [KBAG215Z445]
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Novel polycyclic pi-conjugated dihydropyridazines, pyridazines, and pyrroles were synthesized using various reactions, with all dihydropyridazines showing absorbance and emission at long wavelengths.
The synthesis of novel polycyclic pi-conjugated dihydropyridazines, pyridazines, and pyrroles was studied. Dihydropyridazine dyes were synthesized by inverse electron-demand Diels-Alder cycloaddition reactions between a dibenzosuberenone and tetrazines that bear various substituents. The pyridazines were synthesized in high yields by oxidation of dihydropyridazine-appended dibenzo-suberenones with PIFA or NO. p-Quinone derivatives of pyridazines were also obtained by H-shift isomerization following the inverse electron-demand Diels-Alder reaction of tetrazines withp-quinone dibenzosuberenone. Then these pyridazines were converted to the corresponding pyrroles by reductive treatment with zinc. It was observed that all the dihydropyridazines obtained gave absorbance and emission at long wavelengths.
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