Abstract
Ethyl 3-tert-butyl-4-oxo-7-X-4,6-dihydropyrazolo[5,1-c][1,2,4]triazine-8-carboxylates (X = H, Cl, Br) were synthesized for the first time by diazotization of 7-amino-3-tert-butyl-4oxo-8-ethoxycarbonyl-6H-pyrazolo[5,1-c][1,2,4]triazines with tert-butyl nitrite in the presence of trimethylsilyl halides. A new method was developed: a reaction between 7-amino-3-tert-butyl-4-oxo-6H-pyrazolo[5,1-c][1,2,4]triazine-8-carboxylic acid and I2/TEA followed by treatment with NaBH4 led to a mild decarboxylation. The acid reacts with N-halosuccinimides to give novel 8-halo-substituted derivatives. The amino groups of the latter were acylated by treatment with trifluoroacetic anhydride to give monoacylation products.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 0727—0731, April, 2017.
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Ivanov, S.M., Mironovich, L.M., Rodinovskaya, L.A. et al. Synthesis of new halo-substituted pyrazolo[5,1-c][1,2,4]triazines. Russ Chem Bull 66, 727–731 (2017). https://doi.org/10.1007/s11172-017-1801-0
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DOI: https://doi.org/10.1007/s11172-017-1801-0