Phase‐Transfer‐Catalyzed Interrupted Barton–Zard Reaction Between Electron‐Deficient Indoles and Benzophenone‐Derived Isocyanides
A cascade reaction enabling the construction of pyrrolo[3,4‐ b ]indole core from electron‐deficient and benzophenone‐derived isocyanide precursors under phase‐transfer conditions is described. This transformation proceeds in the presence of a quaternary ammonium catalyst and cesium carbonate, affording functionalized polycyclic cores. The reaction follows the interrupted Barton–Zard reaction pathway and tolerates a broad range of 3‐nitroindole and isocyanide substrates. Performed control experiments provide insight into the generally moderate product yields and clarify why the reaction is not amenable to asymmetric induction.
Authors
- Ana Mikleušević
- Mateja Matišić (ORCID: https://orcid.org/0000-0002-8322-6931)
- Ines Bašić
- Matija Gredičak
- Josip Rešetar
Institutions
- Ruđer Bošković Institute (HR)
Publication Details
- Journal
- European Journal of Organic Chemistry
- Published
- 2026-04-20
- DOI
- https://doi.org/10.1002/ejoc.70464
- Primary Topic
- Multicomponent Synthesis of Heterocycles
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Hrvatska Zaklada za Znanost
- Ministry of Science and Technology, Croatia