Synthesis of new halo-substituted pyrazolo[5,1-c][1,2,4]triazines |
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Authors: | Ivanov S. M. Mironovich L. M. Rodinovskaya L. A. Shestopalov A. M. |
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Affiliation: | 1.N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation ;2.Southwest State University, 94 ul. 50 let Octyabrya, 305040, Kursk, Russian Federation ; |
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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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