Comprehensive Review on the Synthesis of [1,2,3]Triazolo[1,5‐a]Quinolines

• Published in: Chemical record 2024-11, Vol.24 (11), p.e202400107-n/a
• Main Authors: Da Costa, Gabriel P., Sacramento, Manoela, Barcellos, Angelita M., Alves, Diego
• Format: Article
• Language: English
• Subjects: [1,2,3]triazolo[1,5-a]quinoline; metal catalysis; organocatalysis; quinoline; triazoles
• ISSN: 1527-8999; 1528-0691
• DOI: 10.1002/tcr.202400107

This report outlines the evolution and recent progress about the different protocols to synthesize the N‐heterocycles fused hybrids, specifically [1,2,3]triazolo[1,5‐a]quinoline. This review encompasses a broad range of approaches, describing several reactions for obtaining this since, such as dehydrogenative cyclization, oxidative N−N coupling, Dieckmann condensation, intramolecular Heck, (3+2)‐cycloaddition, Ullman‐type coupling and direct intramolecular arylation reactions. We divided this review in three section based in the starting materials to synthesize the target [1,2,3]triazolo[1,5‐a]quinolines. Starting materials containing quinoline or triazole units previously formed, as well as starting materials which both quinoline and triazole units are formed in situ. Different methods of obtaining are described, such as metal‐free or catalyzed conditions, azide‐free, using conventional heating or alternative energy sources, such as electrochemical and photochemical methods. Mechanistic insights underlying the reported reactions were also described in this comprehensive review. This feature article aims to review the evolution and recent advances in different protocols for synthesizing fused hybrids of N‐heterocycles, specifically [1,2,3]triazolo[1,5‐a] quinoline. Approaches to synthesize this unit will be discussed, including dehydrogenative cyclization, N−N oxidative coupling, Dieckmann condensation, intramolecular Heck reactions, (3+2) cycloaddition, Ullmann‐type coupling, and direct intramolecular arylation reactions.