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Synthesis of dibromo-triazoles and their amination with hydroxylamine-O-sulphonic acid
Materials Research Innovations Pub Date : 2014-07-01 , DOI: 10.1179/1432891714z.000000000861
H-X. Yu 1 , H-X. Niu 1 , Y. Wang 1 , Y-C. Li 1 , S-P. Pang 1
Affiliation  

Abstract N-heterocyclic compounds have a wide range of applications in medicinal chemistry, bio-conjugation and materials chemistry due to their high biological activity, low toxicity and high systemic nature. Dibromo-triazoles and their amino derivatives are important functional materials. 3,5-Dibromo-4H-1,2,4-triazole (1, yield 74%) can be easily synthesised from 1H-1,2,4-triazole (2) using bromine, N-bromosuccinimide or other brominating agents in a high yield. The 3,5-dibromo-4-amino-1,2,4-triazole and 3,5-dibromo-1-amino-1,2,4-triazole (3, yield 21%) can be prepared by reacting compound 1 with hydroxylamine-O-sulphonic acid in weakly alkaline aqueous solutions at reflux temperature. Pure compound 3, a colourless solid, was finally obtained after a column chromatography. 4,5-dibromo-1-amino-1,2,3-triazole and 4,5-dibromo-2-amino-1,2,3-triazole (4, yield 30%) can also be prepared with 1H-1,2,3-triazole (5) as the starting reactant and 4,5-dibromo-1H-1,2,3-triazole (6, yield 78%) as the intermediate. The structures of the compounds above were confirmed using 1H-NMR, 13C-NMR, infrared (IR), LC-MS, XRD and elementary analysis. According to the characterisation results, these compounds have two isomers.

中文翻译:

二溴三唑的合成及其羟胺-O-磺酸的胺化

摘要N-杂环化合物具有高生物活性,低毒性和高系统性等特点,在药物化学,生物共轭和材料化学领域具有广泛的应用。二溴三唑及其氨基衍生物是重要的功能材料。3,5-Dibromo-4H-1,2,4-triazole(1,产率74%)可以使用溴,N-溴代琥珀酰亚胺或其他溴化剂从1H-1,2,4-三唑(2)轻松合成高产量。3,5-二溴-4-氨基-1,2,4-三唑和3,5-二溴-1-氨基-1,2,4-三唑(3,收率21%)可以通过使化合物1反应来制备。在回流温度下,在弱碱性水溶液中与羟胺-O-磺酸混合使用。在柱色谱法后,最终获得纯化合物3,为无色固体。4,5-二溴-1-氨基-1,2,3-三唑和4,5-二溴-2-氨基-1,2,还可以使用1H-1,2,3-三唑(5)作为起始反应物和4,5-二溴-1H-1,2,3-三唑(6,收率78%)作为中间体。使用1 H-NMR,13 C-NMR,红外(IR),LC-MS,XRD和元素分析确认以上化合物的结构。根据表征结果,这些化合物具有两个异构体。
更新日期:2014-07-01
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