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Synthesis and photolysis of 3-tert-butyl-4-oxy(mercapto)-1,4-dihydropyrazolo[5,1-c][1,2,4]triazines
Russian Chemical Bulletin ( IF 1.7 ) Pub Date : 2020-04-01 , DOI: 10.1007/s11172-020-2825-4
S. M. Ivanov , K. A. Lyssenko , V. F. Traven

Reactions of 3-tert-butyl- or 3,4-di-tert-butyl-substituted 8-methylpyrazolo[5,1-c][1,2,4]-triazines with trifluoroacetic anhydride afforded 1-(2,2,2-trifluoroacetyl)-1,4-dihydropyrazolo-[5,1-c][1,2,4]triazin-4-yl 2,2,2-trifluoroacetates. The treatment with H2X and RXH (X = O or S; R = Me or Et) of covalent trifluoroacetate that does not contain the But group at the C(4) atom allowed us to synthesize 1-(3-tert-butyl-4-R-pyrazolo[5,1-c][1,2,4]triazin-1(4H)-yl)-2,2,2-trifluoroethan-1-ones. The structure of 4-ethylthio derivative was fully established by the single-crystal X-ray diffraction analysis. The UV irradiation of obtained 2,2,2-trifluoroethan-1-ones leads to the aromatization of triazine ring. The UV photolysis of 1-trifluoroacetyl-4-hydroxy derivative has been proposed as a novel method for the photogeneration of acidity. Antimicrobial and antifungal activities of the synthesized compounds were evaluated.

中文翻译:

3-叔丁基-4-氧基(巯基)-1,4-二氢吡唑并[5,1-c][1,2,4]三嗪的合成与光解

3-叔丁基或 3,4-二叔丁基取代的 8-甲基吡唑并[5,1-c][1,2,4]-三嗪与三氟乙酸酐反应得到 1-(2,2, 2-三氟乙酰基)-1,4-二氢吡唑并-[5,1-c][1,2,4]三嗪-4-基2,2,2-三氟乙酸酯。用 H2X 和 RXH(X = O 或 S;R = Me 或 Et)处理在 C(4) 原子上不含 But 基团的共价三氟乙酸酯使我们能够合成 1-(3-tert-butyl-4 -R-吡唑并[5,1-c][1,2,4]triazin-1(4H)-yl)-2,2,2-trifluoroethan-1-ones。通过单晶X射线衍射分析完全确定了4-乙硫基衍生物的结构。得到的 2,2,2-trifluoroethan-1-ones 的紫外线照射导致三嗪环的芳构化。1-三氟乙酰基-4-羟基衍生物的紫外光解已被提出作为一种光产生酸度的新方法。
更新日期:2020-04-01
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