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.

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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

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article

Phase‐Transfer‐Catalyzed Interrupted Barton–Zard Reaction Between Electron‐Deficient Indoles and Benzophenone‐Derived Isocyanides

Ana Mikleušević, Mateja Matišić, Ines Bašić, Matija Gredičak et al.
European Journal of Organic Chemistry
Multicomponent Synthesis of Heterocycles
article

Phase‐Transfer‐Catalyzed Interrupted Barton–Zard Reaction Between Electron‐Deficient Indoles and Benzophenone‐Derived Isocyanides

Ana Mikleušević, Mateja Matišić, Ines Bašić, Matija Gredičak, Josip Rešetar
article en

Abstract

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.

European Journal of Organic Chemistry
Ruđer Bošković Institute (HR)
Hrvatska Zaklada za Znanost, Ministry of Science and Technology, Croatia
Openalex Percentile: Top 8%
Multicomponent Synthesis of Heterocycles
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