芳酰基脲及硫脲类化合物的绿色合成与研究
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摘要
环境友好化学过程是当前化学研究和发展的重要部分。水介质中的有机化学反应,研磨条件下进行的有机反应等绿色合成手段已经吸引了许多化学工作者的关注,当有机反应在以上条件下进行时,由于未使用传统的有机溶剂,因而反应成本,反应安全,环境保护,生产效率和选择性方面都有了很大的提高。同时反应的速度也大大提高,因此以上手段是较为理想的合成方法。
脲类,硫脲类化合物是一类用途广泛的化合物,如用作染料,抗氧化剂,杀虫剂,药物合成中间体等。目前,化学和医药工作者正在对它们进行深入地研究和开发,期望获得具有更高、更广泛的生物活性的先导化合物。
本文主要介绍了以30%浓度的双氧水作为氧化剂氧化硫脲、氨基硫脲来制备相应的脲和氨基脲类化合物。另外,进一步地探讨和优化了在水介质形成中间体酰基异硫氰酸酯的条件,并以此为基础合成了相关的硫脲类化合物。
本论文分为五章:
第一章:综述了近些年来在水介质中和研磨条件下进行的有机合成进展情况,这些反应与传统在有机溶剂中进行的反应相比较,具有对环境友好,反应速度快,产率高,后处理简单等优点。
第二章和第四章以30%双氧水作为氧化剂,绿色合成了酰基脲类化合物,该方法与传统的方法相比较,具有反应速度快,产率高,成本低廉,对环境友好,后处理简单等好处。
第三章:探讨了以苄基三乙基氯化铵(TEBA)为相转移催化剂,以酰氯、硫氰酸铵为反应底物,在水相中合成重要的中间体酰基异硫氰酸酯,继而加入芳胺,高产率地合成了酰基硫脲类化合物,为绿色合成此类化合物提供了一种可行的途径。
所合成化合物的结构用元素分析、红外光谱及核磁共振氢谱进行了表征,并对波谱数据进行了分析。
Environmentally friendly chemical process is the vital part of the current chemical research and development. Organic reactions in water media and carried out via grinding have attracted more and more attention from chemists because they have many potential advantages and benefits in terms of cost, safety, environmental concerns, efficiency, and selectivity. Meanwhile, above methods are practical and worthwhile because of simple reaction conditions and high reaction rates.
Ureas and thioureas are used widely such as: applications as dyes, antioxidants, pesticides, corrosion inhibitors, intermediates for the preparation of pharmaceuticals, and agricultural chemicals. Recently, in order to get better active compounds, chemistry and medicine researchers are doing further research on them. This thesis mainly introduced that ureas and semicarbazides were synthesized by oxidation of corresponding thioureas and thiosemicarbazides using 30% peroxide as oxidant. In addition, we further discussed about reaction conditions for synthesizing isothiocyanide in aqueous media. And based on the above reaction conditions, some related thioureas were prepared successfully in high yields.
This thesis contains four chapters, they are:
Chapter 1: Some of organic reactions in aqueous and by grinding were reviewed in this chapter. Compared with traditional methods, they are environmental, rapid, high yields, simple work-up and so on.
Chapter 2 and 4: ureas/semicarbazides were synthesized using 30% peroxide hydrogen as oxidant. Compared with the traditional methods, our procedures have advantages of high reaction rates, excellent yields, benign to environment and simple work-up procedure.
Chapters 3: We synthesized important intermediate in water used acyl chloride, ammonium thiocyanate and TEBA as starting materials and phase transfer catalyst respectively, then Aryl amine was added to the mixture and corresponding thioureas were obtained in good yields. In addition, we further discussed about the reaction conditions. It also provides a feasible and clean way for synthesizing this kind of compounds.
The structures of all compounds were confirmed by elemental analysis, IR and ~1H NMR.
脲类,硫脲类化合物是一类用途广泛的化合物,如用作染料,抗氧化剂,杀虫剂,药物合成中间体等。目前,化学和医药工作者正在对它们进行深入地研究和开发,期望获得具有更高、更广泛的生物活性的先导化合物。
本文主要介绍了以30%浓度的双氧水作为氧化剂氧化硫脲、氨基硫脲来制备相应的脲和氨基脲类化合物。另外,进一步地探讨和优化了在水介质形成中间体酰基异硫氰酸酯的条件,并以此为基础合成了相关的硫脲类化合物。
本论文分为五章:
第一章:综述了近些年来在水介质中和研磨条件下进行的有机合成进展情况,这些反应与传统在有机溶剂中进行的反应相比较,具有对环境友好,反应速度快,产率高,后处理简单等优点。
第二章和第四章以30%双氧水作为氧化剂,绿色合成了酰基脲类化合物,该方法与传统的方法相比较,具有反应速度快,产率高,成本低廉,对环境友好,后处理简单等好处。
第三章:探讨了以苄基三乙基氯化铵(TEBA)为相转移催化剂,以酰氯、硫氰酸铵为反应底物,在水相中合成重要的中间体酰基异硫氰酸酯,继而加入芳胺,高产率地合成了酰基硫脲类化合物,为绿色合成此类化合物提供了一种可行的途径。
所合成化合物的结构用元素分析、红外光谱及核磁共振氢谱进行了表征,并对波谱数据进行了分析。
Environmentally friendly chemical process is the vital part of the current chemical research and development. Organic reactions in water media and carried out via grinding have attracted more and more attention from chemists because they have many potential advantages and benefits in terms of cost, safety, environmental concerns, efficiency, and selectivity. Meanwhile, above methods are practical and worthwhile because of simple reaction conditions and high reaction rates.
Ureas and thioureas are used widely such as: applications as dyes, antioxidants, pesticides, corrosion inhibitors, intermediates for the preparation of pharmaceuticals, and agricultural chemicals. Recently, in order to get better active compounds, chemistry and medicine researchers are doing further research on them. This thesis mainly introduced that ureas and semicarbazides were synthesized by oxidation of corresponding thioureas and thiosemicarbazides using 30% peroxide as oxidant. In addition, we further discussed about reaction conditions for synthesizing isothiocyanide in aqueous media. And based on the above reaction conditions, some related thioureas were prepared successfully in high yields.
This thesis contains four chapters, they are:
Chapter 1: Some of organic reactions in aqueous and by grinding were reviewed in this chapter. Compared with traditional methods, they are environmental, rapid, high yields, simple work-up and so on.
Chapter 2 and 4: ureas/semicarbazides were synthesized using 30% peroxide hydrogen as oxidant. Compared with the traditional methods, our procedures have advantages of high reaction rates, excellent yields, benign to environment and simple work-up procedure.
Chapters 3: We synthesized important intermediate in water used acyl chloride, ammonium thiocyanate and TEBA as starting materials and phase transfer catalyst respectively, then Aryl amine was added to the mixture and corresponding thioureas were obtained in good yields. In addition, we further discussed about the reaction conditions. It also provides a feasible and clean way for synthesizing this kind of compounds.
The structures of all compounds were confirmed by elemental analysis, IR and ~1H NMR.
引文
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