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Synthesis of 3H-1,2,4-Triazol-3-ones via NiCl2-Promoted Cascade Annulation of Hydrazonoyl Chlorides and Sodium Cyanate.

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A nickel-promoted cascade annulation reaction for the facile synthesis of 3H-1,2,4-triazol-3-ones from readily available hydrazonoyl chlorides and sodium cyanate has been developed. The transformation occurs through a cascade nickel-promoted intermolecular… Click to show full abstract

A nickel-promoted cascade annulation reaction for the facile synthesis of 3H-1,2,4-triazol-3-ones from readily available hydrazonoyl chlorides and sodium cyanate has been developed. The transformation occurs through a cascade nickel-promoted intermolecular nucleophilic addition-elimination process, intramolecular nucleophilic addition, and a hydrogen-transfer sequence. The method has been successfully applied for the construction of the core skeleton of the angiotensin II antagonist.

Keywords: hydrazonoyl chlorides; chlorides sodium; promoted cascade; triazol ones; synthesis triazol; cascade annulation

Journal Title: Organic letters
Year Published: 2021

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