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- Title
The Dimroth rearrangement of 5-amino-1-aryl-1,2,3-triazole-4-carbothioamides.
- Authors
Ilkin, Vladimir G.; Dianova, Lidiya N.; Bakulev, Vasiliy A.; Berseneva, Vera S.; Saveliev, Dmitry A.; Beryozkina, Tetyana V.
- Abstract
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.
- Subjects
MASS spectrometry; METHOXY group; HALOGEN compounds; NUCLEAR magnetic resonance spectroscopy; ARYL group
- Publication
Chemistry of Heterocyclic Compounds, 2020, Vol 56, Issue 10, p1335
- ISSN
0009-3122
- Publication type
Article
- DOI
10.1007/s10593-020-02819-w