Access to Amides and Lactams via Pyridotriazole as a Transformable Directing Group

Chen, Yuting; Li, Zhiyang; Xu, Yanning; Huang, Tianle; Hai, Li; Nie, Ruifang; Wu, Yong

doi:10.1021/acs.joc.3c01490

Cited by 2 publications

(1 citation statement)

References 60 publications

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“…This heteroaryl core underscores compounds with potent biological activity, including the clinically relevant antidepressant trazodone. Recent advancements in metal-mediated transformations have realized gains in denitrogenation to afford functionalized amides and lactams, N–H insertion reactions, and photoredox approaches to arene sulfonation . The pursuit of new heteroaryl soft-N-donors for complexation of the minor actinides from lanthanides contained in spent nuclear fuel continues to garner interest in the development of synthetic methods to afford new materials to improve metal:ligand selectivity, binding, and the definition of structure–activity relationships.…”

Section: Introductionmentioning

confidence: 99%

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

Edirin,

Carrick

2024

J. Org. Chem.

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

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Section: Introductionmentioning

confidence: 99%

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

Edirin,

Carrick

2024

J. Org. Chem.

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

Qin,

Wang,

Cao

et al. 2024

J. Org. Chem.

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With the assistance of nickel as catalyst, 2,2′-bipyridine (bpy) as ligand, and manganese as reducing metal, the reductive amidation of 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 the facile synthesis of a range of structurally diverse amides in moderate to high yields with broad functionality compatibility. In addition, the synthetic usefulness of the method was further demonstrated by applying the reaction in scale-up synthesis and the late-stage functionalization of complex molecules with biological activities.

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Access to Amides and Lactams via Pyridotriazole as a Transformable Directing Group

Cited by 2 publications

References 60 publications

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

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

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

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