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Green microwave versus conventional synthesis, crystal structure of 1-(4-(Benzothiazol-2-yl)piperazin-1-yl)-2-(4-phenyl-1H-1,2,3-triazol-1-yl)ethenone and HS-Analysis
Journal of Taibah University for Science ( IF 2.8 ) Pub Date : 2020-04-15 , DOI: 10.1080/16583655.2020.1751977
Musa A. Said 1 , Mouslim Messali 1 , Nadjet Rezki 1, 2 , Yaseen A. Al-Soud 3 , Mohamed R. Aouad 1, 2
Affiliation  

This study reports an efficient eco-friendly microwave assisted synthesis of 1-(4-(benzothiazol-2-yl)piperazin-1-yl)-2-(4-phenyl-1H-1,2,3-triazol-1-yl)ethanone (4) through the click cyclocondensation of 2-azido-1-(4-(benzo[d]thiazol-2-yl)piperazin-1-yl)ethanone (3) with phenyl acetylene. The synthesis was carried out under optimized copper catalyst copper(II) sulfate pentahydrate/sodium ascorbate, t-BuOH/water (1:1, v/v) to afford the regioselective 1,4-disubstituted 1,2,3-triazole isomer. The reactions were greatly accelerated using microwave irradiation. The new designed 1,2,3-triazole was fully characterizid by IR, NMR, MS spectral data and X-ray diffraction. The crystal structure of 4 demonstrated a conventional chair conformation for the piperazine ring. Interesting Hirshfeld Surface Analysis (HAS) was conducted showing clear agreement with the XRD analysis.



中文翻译:

绿色微波与常规合成的关系,1-(4-(苯并噻唑-2-基)哌嗪-1-基)-2-(4-苯基-1H-1,2,3-三唑-1-基)乙酮的晶体结构和HS分析

这项研究报告了高效的环保微波辅助合成1-(4-(苯并噻唑-2-基)哌嗪-1-基)-2-(4-苯基-1 H -1,2,3-三唑-1 -基)乙酮(4)通过2-叠氮基-1-(4-(苯并[点击环化缩合d ]噻唑-2-基)哌嗪-1-基)乙酮(3)与苯基乙炔。在优化的铜催化剂下合成五水合硫酸铜(II)五水合/抗坏血酸钠,t- BuOH /水(1:1,v / v),得到区域选择性的1,4-二取代的1,2,3-三唑异构体。使用微波辐射极大地促进了反应。通过IR,NMR,MS光谱数据和X射线衍射对新设计的1,2,3-三唑进行了完全表征。4的晶体结构证明了哌嗪环的常规椅子构型。进行了有趣的Hirshfeld表面分析(HAS),与XRD分析显示出明显的一致性。

更新日期:2020-04-15
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