Summary.
A novel coupling reaction of 4-amino-5-mercapto-3-substituted-1,2,4-triazoles to generate symmetrically substituted hydrazines, N,N′-bis(5-mercapto-3-substituted-1,2,4-triazol-4-yl)hydrazines was unexpectedly observed. Five examples are presented to demonstrate this reaction. All isolated products were unambiguously characterized.
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Triazoles 1 were readily prepared according to the earlier reports, Sasaki T, Ito E (1981) J Heterocyclic Chem 18: 1353; Reid JR, Heindel ND (1976) J Heterocyclic Chem 13: 925
Compound 2 was readily prepared by the well-known Pummerer rearrangement according to Russell GA, Mikol GJ (1966) J Am Chem Soc 88: 5498
This conclusion has been verified unambiguously by X-ray diffraction method. Please see our previous research result concerning a similar tautomerism for reference, Wen LR, Li GQ, Li M, Jing SX, Zhang SS (2003) Chinese J Structural Chem 22: 529
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Li, M., Zhao, G., Wen, L. et al. A Coupling Reaction of 4-Amino-5-mercapto- 3-substituted-1,2,4-triazoles to Generate Symmetrically Substituted Hydrazines. Monatsh. Chem. 136, 2045–2049 (2005). https://doi.org/10.1007/s00706-005-0372-1
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DOI: https://doi.org/10.1007/s00706-005-0372-1