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The Dimroth rearrangement of 5-amino-1-aryl-1,2,3-triazole-4-carbothioamides

Chemistry of Heterocyclic Compounds Aims and scope

The rearrangement of 5-amino-1-aryl-1,2,3-triazole-4-carbothioamides was investigated. The process was optimized by varying the solvent, temperature, and the type of base. The optimal reaction conditions were found, and new 1-unsubstituted 5-arylamino-1,2,3-triazole-4-carbothioamides were synthesized. It has been shown that 1-aryl-1,2,3-triazoles containing a nitro group in the para position undergo rearrangement upon heating under reflux in n-butanol in the absence of a base. The rearrangement of compounds containing halogen, hydrogen, methyl, or methoxy groups in the aryl moiety requires the use of a base. The structure of the obtained compounds was confirmed by the data of NMR spectroscopy and mass spectrometry.

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Figure 1
Scheme 1

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This work was supported by the Russian Foundation for Basic Research (grant 18-03-00715).

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Correspondence to Tetyana V. Beryozkina.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(10), 1335–1340

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Ilkin, V.G., Dianova, L.N., Bakulev, V.A. et al. The Dimroth rearrangement of 5-amino-1-aryl-1,2,3-triazole-4-carbothioamides. Chem Heterocycl Comp 56, 1335–1340 (2020). https://doi.org/10.1007/s10593-020-02819-w

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