4.5 Article

Synthesis and Properties of Thieno[3,2-f]isoquinolines and Benzothieno[3,2-f]isoquinolines

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2022, Issue 8, Pages -

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202101306

Keywords

Catalysis; Cross-Coupling; Cyclizations; Heterocycles; Thienoisoquinolines

Funding

  1. DAAD
  2. State of Mecklenburg-Vorpommern

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A variety of thieno[3,2-f]isoquinolines were synthesized by combining Pd catalysed cross-coupling reactions with Bronsted acid mediated cycloisomerisations, with high selectivity towards various functional groups. In addition, benzothieno[3,2-f]isoquinolines were prepared, representing a new heterocyclic core structure. The optical properties of selected compounds were studied, and solvatochromism characteristic of intramolecular charge transfer was observed for one compound with a push-pull structure.
A variety of thieno[3,2-f]isoquinolines were prepared by combination of Pd catalysed cross-coupling reactions with Bronsted acid mediated cycloisomerisations. The reactions tolerate various functional groups and proceed with high selectivity. In addition, benzothieno[3,2-f]isoquinolines were prepared which represent a new heterocyclic core structure. The optical properties of selected compounds were studied by experimental and theoretical methods. Emission solvatochromism, characteristic of intramolecular charge transfer was observed for one of the compounds with a push-pull structure.

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