Synthesis of 1,2,3-triazole-fused heterocycles viaPd-catalyzed cyclization of 5-iodotriazoles

Abstract

A convenient approach toward polycyclic frameworks containing fused 1,2,3-triazoles is described. The synthesis consists of a Cu-catalyzed cycloaddition and an intramolecular Pd-catalyzed direct arylation or Heck reaction, and affords the products in good to excellent yields.

Nickel‐ or Palladium‐Catalyzed Stereoselective Synthesis of Tetrasubstituted Olefinic Indolines‐Fused Triazoles: Extension to the Spiroindoline Core

“…Likewise 1,2,3‐ triazoles have also found far‐flung use in medicinal chemistry, chemical biology and material chemistry 2. While a variety of approaches to indolines3 and triazoles2,4 have been described, only a few synthetic methods has been discovered to afford isoindolines‐fused triazoles5 and these class of compounds possess interesting biological properties 5d. The syntheses of indolines‐fused triazoles were also reported in the literature, but only as minor by‐products 5e–h…”

Regioselective Synthesis of Halotriazoles and their Utility in Metal Catalyzed Coupling Reactions

“…Later 1,2,3‐triazole‐fused isoindolines 83 were synthesized via annulation of the 5‐iodo‐1,2,3‐triazole 84 onto the benzyl protecting group using Pd(OAc) 2 as the catalyst. [ 47 ]…”

Palladium‐Catalyzed Annulation of Aryltriazoles and Arylisoxazoles with Alkynes

“…However, to realize the selective cleavage of the undirected C−H bond of triazole in the presence of other aromatic C−H bonds is extremely challenging . An alternative strategy is the application of triazole iodide intermediate in an intramolecular arylation reaction (Scheme A) . In 2016, Lautens group reported a Cu/Pd‐catalyzed alkyne insertion/C−H functionalization strategy to achieve seven‐membered pocyclic triazoles (Scheme B) .…”