Synthesis of 2H-1,2,3-triazole-4-carboxylic acids via Ru(II)-catalyzed rearrangement of 4-hydrazonoisoxazol-5-ones

[Display omitted] An atom-economy, two-step synthesis of 2H-1,2,3-triazole-4-carboxylic acids from 3-arylisoxazol-5(4H)-ones and arenediazonium tetrafluoroborates is described. The formation of the 1,2,3-triazole ring is achieved by the [Ru(p-cymene)Cl2]2-catalyzed rearrangement of 4-hydrazonoisoxaz...

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Bibliographic Details
Published in:Tetrahedron letters 2023-06, Vol.123, p.154580, Article 154580
Main Authors: Vasilchenko, Dmitrii S., Agafonova, Anastasiya V., Simdianov, Ivan V., Koronatov, Alexander N., Sakharov, Pavel A., Romanenko, Ilya A., Rostovskii, Nikolai V., Khlebnikov, Alexander F., Novikov, Mikhail S.
Format: Article
Language:English
Subjects:
1,2,3-Triazoles
Diazonium salts
Isoxazol-5(4H)-ones
Rearrangements
Ruthenium catalysis
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Summary:[Display omitted] An atom-economy, two-step synthesis of 2H-1,2,3-triazole-4-carboxylic acids from 3-arylisoxazol-5(4H)-ones and arenediazonium tetrafluoroborates is described. The formation of the 1,2,3-triazole ring is achieved by the [Ru(p-cymene)Cl2]2-catalyzed rearrangement of 4-hydrazonoisoxazol-5-ones which are resulted from the diazo coupling. The advantages of the method include the available starting compounds and the ability to purify target acids without the use of chromatography.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2023.154580