Indium(III)-Catalyzed Synthesis of Pyrroles and Benzo[<i>g</i>]indoles by Intramolecular Cyclization of Homopropargyl Azides.

ABSTRACT: Pyrroles, privileged structural motifs in drug and material science, have been synthesized by indium(III)-catalyzed intramolecular cyclization of homopropargyl azides. This methodology exhibits a broad substrate scope, providing substituted pyrroles and bispyrroles in good yields. Furthermore, an atom-economical sequential method for the synthesis of benzo[g]indoles has been discovered from azido-diynes using InCl₃ as catalyst. The method involves two successive intramolecular indium-catalyzed 5-endo-dig alkyne hydroamination and a hydroarylation reactions with 6-endo-dig regioselectivity.

SUBMITTER: Da Lama A 

PROVIDER: S-EPMC11536385 | biostudies-literature | 2024 Nov

REPOSITORIES: biostudies-literature