Synthesis of Fused [1,2,3]-Triazoloheteroarenes via Intramolecular Azo Annulation of N-Tosylhydrazones Catalyzed by 1,8-Diaza-bicyclo[5.4.0]undec-7-ene

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(10), P. 7201 - 7209

Published: May 3, 2024

The structural diversity of triazoloheteroarenes render this moiety an attractive synthon for drug discovery, C–H functionalization, and complexant design minor actinide separations. While contemporary work has demonstrated the capacity to leverage downstream functional group interconversion triazolopyridine, a broadly applicable method tolerant diverse heteroaryl constructs pendant functionality obtain remains under reported. In work, serendipitous discovery metal, azide, oxidant free transformation various N-tosylhydrazones carbaldehydes ketones corresponding [1,2,3]-triazoloheteroarene via intramolecular azo annulation using substoichiometric amount 1,8-diaza-bicyclo[5.4.0]undec-7-ene is described. These results substantively improve upon previous approaches offering efficient access described heterocycles. Discovery reaction conditions, optimization, complexant, pyridine, heteroarene substrate scope, as well relevant scale-up reactions are reported herein.

Language: Английский

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Nickel-Catalyzed Reductive Amidation of Aryl Fluorosulfates with Isocyanates: Synthesis of Amides via C–O Bond Cleavage

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 30, 2024

With the assistance of nickel as catalyst, 2,2'-bipyridine (bpy) ligand, and manganese reducing metal, reductive amidation isocyanates with readily accessible aryl fluorosulfates could be successfully accomplished. The reactions proceeded effectively via C-O bond activation in DMF at room temperature, enabling facile synthesis a range structurally diverse amides moderate to high yields broad functionality compatibility. In addition, synthetic usefulness method was further demonstrated by applying reaction scale-up late-stage functionalization complex molecules biological activities.

Language: Английский

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HFIP-Promoted Aromatic Electrophilic Amidation of Indoles and Pyrroles with Isocyanates

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 19, 2025

A mild and practical method for synthesizing amidoindoles amidopyrroles was described via the direct amidation of indoles or pyrroles with isocyanates promoted by 1,1,1,3,3,3-hexafluoroisopropanol (HFIP). In this reaction, HFIP acted as a strong hydrogen bond-donating solvent to activate isocyanates, enabling electron-rich nitrogen-containing heterocycles.

Language: Английский

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Denitrogenative transformations of aryl-fused 1,2,3-triazoles

Advances in heterocyclic chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Language: Английский

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