Synthesis of Thienoindoles

  • Author: Veronika Belusa
  • Published: 08 July 2015
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
  • Source / Publisher: Beilstein Journal of Organic Chemistry/Beilstein Institut
thumbnail image: Synthesis of Thienoindoles

Roman A. Irgashev, Ural Division of the Russian Academy of Sciences, Ekaterinburg, Russia, and colleagues have developed a short and robust synthesis of 2-(hetero)aryl substituted thieno[2,3-b]indoles (pictured) from easily available 1-alkylisatins and acetylated (hetero)arenes.


The two-step approach includes the "aldol-crotonic" type condensation of N-alkylated isatins with acetophenones or their heterocyclic analogues. This is followed by treatment of the intermediate 3-(2-oxo-2-(hetero)arylethylidene)indolin-2-ones with Lawesson’s reagent. The latter process involves two sequential reactions, namely the reduction of the C=C ethylidene double bond of the intermediate indolin-2-ones, followed by a Paal–Knorr cyclization.


According to the researchers, this approach provides easy access to compounds of the electron-rich thieno[2,3-b]indole family. They are seen as promising building-blocks for the development of new photo- and electrosensitive molecules, e.g., novel push-pull dyes for dye-sensitized solar cells.


 

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