Synthesis of Diaza[5]helicenes by ortho,ortho′-Fusion of ortho-Terphenyls
| Autor: | Joachim Podlech, Stefan Herzog, Inka Marten, Aaron Weiß |
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| Rok vydání: | 2022 |
| Předmět: | |
| Zdroj: | Synthesis. 54:4220-4234 |
| ISSN: | 1437-210X 0039-7881 |
| DOI: | 10.1055/a-1804-8980 |
| Popis: | Double ortho-fusion in suitably substituted ortho-terphenyls was used for the synthesis of diaza[5]helicenes. Bis(carboxamido)-substituted ortho-terphenyls can be condensed to 5,9- and 6,9-diaza[5]helicenes, where substituents at the 6,10- and 5,10-positions, respectively, are introduced with the carboxamido groups. While a twofold coupling sequence with intermediate protection of one amino group has to be used for 5,9-diaza[5]helicenes, a more concise sequence avoiding the protection leads to 6,9-diaza[5]helicenes. The simple heating of ortho,ortho′-diazidoterphenyls furnishes 5,8-dihydroindolo[2,3-c]carbazoles, i.e., [5]helicenes with alternating benzene and pyrrole rings. |
| Databáze: | OpenAIRE |
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