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April 23, 2026European Journal of Organic Chemistry0 citationsOpen Access

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

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AMAna MikleuševićIBInes BašićMMMateja Matišić

Key Points

  • The aim is to develop a method for creating pyrrolo[3,4-b]indole cores from specific precursors using a phase-transfer catalyst.
  • Utilized phase-transfer conditions with a quaternary ammonium catalyst and cesium carbonate.
  • Investigated the reaction pathway of the interrupted Barton–Zard reaction with various substrates.
  • Conducted control experiments to analyze product yields.
  • Achieved construction of functionalized polycyclic cores from a variety of indole and isocyanide substrates.
  • Observed generally moderate yields of the products.
  • Clarified limitations regarding asymmetric induction in this reaction.

Abstract

A cascade reaction enabling the construction of pyrrolo3,4‐ 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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Cite This Study

Mikleušević et al. (2026) studied this question.

synapsesocial.com/papers/69e9ba6b85696592c86ec96ehttps://doi.org/10.1002/ejoc.70464
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