Related Experiment Video
Updated: Jun 10, 2025

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Indium(III)-Catalyzed Synthesis of Pyrroles and Benzo[g]indoles by Intramolecular Cyclization of Homopropargyl Azides
Ana Da Lama1, José Pérez Sestelo1, Luis A Sarandeses1
1CICA, Centro Interdisciplinar de Química e Bioloxía and Departamento de Química, Universidade da Coruña, 15071 A Coruña, Spain.
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.
More Related Videos
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
11:45Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Related Concept Videos
Cycloaddition Reactions: Overview
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Preparation of 1° Amines: Azide Synthesis
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Thermal and Photochemical Electrocyclic Reactions: Overview
Nucleophilic Aromatic Substitution: Elimination–Addition