Ryan M. Alam, John J. Keating

Accessing Dihydropyrrolo[3,4‐b]indol‐1(2H)‐ones via Pd‐Catalyzed Intramolecular Aminocarbonylative Ring Closure

  • Organic Chemistry
  • Physical and Theoretical Chemistry

AbstractPresent in a number of small molecule derivatives that display a wide range of biological activities, the dihydropyrrolo[3,4‐b]indol‐(2H)‐one (DHPI) core represents an underexplored heterocyclic scaffold. Given the pharmaceutical potential of the DHPI motif, the development of synthetic methodologies that permit their expedient assembly would be highly desirable. Herein, we describe a novel strategy for the construction of the DHPI core from 3‐iodo‐1H‐indolyl substrates, employing an unprecedented Pd‐catalyzed intramolecular aminocarbonylative ring closure. The compatibility of our optimized protocol with various functional groups is highlighted through the synthesis of a range of diversely substituted DHPI derivatives in up to 90 % isolated yield.

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