Modifications of 5,12-dihydroindolo[3,2-a]carbazole scaffold via its regioselective C2,9-formylation and C2,9-acetylation |
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Authors: | Nikita A Kazin Nadezhda S Demina Roman A Irgashev Ekaterina F Zhilina Gennady L Rusinov |
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Institution: | 1. Postovsky Institute of Organic Synthesis, Ural Division, Russian Academy of Sciences, S. Kovalevskoy Str., 22, Ekaterinburg, 620990, Russia;2. Ural Federal University Named After the First President of Russia B. N. Yeltsin, Mira Str., 19, Ekaterinburg, 620002, Russia |
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Abstract: | The effective approaches for regioselective double formylation and acetylation of 5,12-dialkyl-6,7-diaryl-substituted 5,12-dihydroindolo3,2-a]carbazoles by their treatment with dichloromethyl methyl ether in the presence of SnCl4 or with acetyl chloride in the presence of AlCl3 to afford the 2,9-diformyl or 2,9-diacetyl derivatives, respectively, were developed. Furthermore, new 2,9-bis(2,2-dicyanovinyl) derivatives were synthesized by the Knoevenagel condensation of diformyl-containing substrates with malononitrile, when new 2,9-bis(quinoxaline-2-yl)- and 2,9-bis(benzog]quinoxaline-2-yl) derivatives were formed via microwave-promoted oxidation of diacetyl-containing substrates with SeO2 to the corresponding diglyoxals, followed by the reaction of these intermediates with o-phenylendiamine or 2,3-diaminonaphthalene, respectively. The basic optical and electrochemical properties of some 5,12-dihydroindolo3,2-a]carbazoles were investigated. |
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Keywords: | Corresponding author Postovsky Institute of Organic Synthesis Ural Division Russian Academy of Sciences S Kovalevskoy Str 22 Ekaterinburg 620990 Russia 5 12-Dihydroindolo[3 2-a]carbazoles Formylation Acetylation Heteroacenes |
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