8‐Fluoro‐4‐hydroxy‐1H‐[1,2,4]triazino[4,5‐a]quinoline‐1,6(2H)‐dione: Synthesis and reactivity

Edmont, Doloràs; Chenault, Jacques

doi:10.1002/jhet.5570400507

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2023

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Cited by 7 publications

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“…Approaches to the heterocyclic core of 1,2,4-triazin-3(2 H )-ones include the use of hydrazine as a nucleophile in ring-opening reactions of oxadiazol-2-one moieties, condensation chemistry with dicarbonyl derivatives, or addition onto isocyanates . Two new approaches to triazinones were recently reported.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 1,2,4-Triazinones Exploiting the Reactivity of Diazadiene and N-Isocyanate Intermediates

et al. 2023

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1,2,4-Triazinones are useful compounds, but their synthesis can be challenging. Herein, we report a strategy to build 1,2,4-triazinones using α-bromohydrazones to access diazadienes and exploiting their ability to undergo facile substitution with nitrogen nucleophiles. The N-isocyanate intermediate formed in situ can then undergo cyclization to give the desired triazinones. This provides access to products with various substituents at the 4-position, and with suitable hydrazone precursors (R 2 = Ph), the cascade reaction yields 1,2,4-triazin-3(2H)-ones at room temperature.

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Section: Introductionmentioning

confidence: 99%