Abdelriheem Nadia A, Zaki Yasser H, Abdelhamid Abdou O
Department of Chemistry, Faculty of Science, Cairo University, Giza, 12613, Egypt.
Department of Chemistry, Faculty of Science, Beni-Suef University, Beni-Suef, 62514, Egypt.
Chem Cent J. 2017 Jun 12;11(1):53. doi: 10.1186/s13065-017-0282-4.
Pyrazolo[1,5-a]pyrimidines are purine analogues. They have beneficial properties as antimetabolites in purine biochemical reactions. This division compounds have attracted wide pharmaceutical interest because of their antitrypanosomal activity.
The present work depicts an effective synthesis convention of pyrazolo[1,5-a]pyrimidines, pyrazolo[5,1-c]triazines, thieno[2,3-b]pyridines and polysubstituted pyridines containing 1,2,3,-triazole moiety from the reaction of sodium 3-(5-methyl-1-(p-toly)-1H-1,2,3-triazol-4-yl)-3-oxoprop-1-en-1-olate with the fitting heterocyclic amines and its diazonium salt, and active methylene compounds, individually. Likewise, thiazoles and, 1,3,4-thiadiazoles were obtained from 2-bromo-1-(5-methyl-1-(p-tolyl)-1H-1,2,3-triazol-4-yl)ethanone and some reagent such as hydrazonoyl chlorides and halo ketones. The newly synthesized compounds were established by elemental analysis, spectral data, and alternative synthetic route whenever possible.
New series of pyrazolo[1,5-a]pyrimidines, pyrazolo[5,1-c]triazines, thieno[2,3-b]pyridines and polysubstituted pyridines containing the 1,2,3,-triazole moiety were synthesized via reactions of sodium 3-(5-methyl-1-(p-toly)-1H-1,2,3-triazol-4-yl)-3-oxoprop-1-en-1-olate with the appropriate heterocyclic amines and its diazonium salt. In addition, 1,3,4-thiadiazoles and, 1,3-thiazoles were acquired in a decent yield via the reaction of substituted thiourea with the appropriate hydrazonoyl chlorides and halogenated ketenes. Graphical abstract Synthesis of some new pyrazolo[1,5-a]pyrimidines, pyrazolo[5,1-c]triazines and thieno[2,3-b]pyridines.
吡唑并[1,5 - a]嘧啶是嘌呤类似物。它们在嘌呤生化反应中作为抗代谢物具有有益特性。由于其抗锥虫活性，这类化合物引起了广泛的药学关注。
本工作描述了一种有效的合成方法，通过3 - (5 - 甲基 - 1 - (对甲苯基) - 1H - 1,2,3 - 三唑 - 4 - 基) - 3 - 氧代丙 - 1 - 烯 - 1 - 醇钠分别与合适的杂环胺及其重氮盐以及活性亚甲基化合物反应，合成含1,2,3 - 三唑部分的吡唑并[1,5 - a]嘧啶、吡唑并[5,1 - c]三嗪、噻吩并[2,3 - b]吡啶和多取代吡啶。同样，通过2 - 溴 - 1 - (5 - 甲基 - 1 - (对甲苯基) - 1H - 1,2,3 - 三唑 - 4 - 基)乙酮与一些试剂如肼酰氯和卤代酮反应得到噻唑和1,3,4 - 噻二唑。新合成的化合物通过元素分析、光谱数据以及尽可能采用的替代合成路线进行确证。
通过3 - (5 - 甲基 - 1 - (对甲苯基) - 1H - 1,2,3 - 三唑 - 4 - 基) - 3 - 氧代丙 - 1 - 烯 - 1 - 醇钠与合适的杂环胺及其重氮盐反应，合成了一系列含1,2,3 - 三唑部分的新型吡唑并[1,5 - a]嘧啶、吡唑并[5,1 - c]三嗪、噻吩并[2,3 - b]吡啶和多取代吡啶。此外，通过取代硫脲与合适的肼酰氯和卤代烯酮反应，以良好的产率得到了1,3,4 - 噻二唑和1,3 - 噻唑。图形摘要：一些新型吡唑并[1,5 - a]嘧啶、吡唑并[5,1 - c]三嗪和噻吩并[2,3 - b]吡啶的合成。
