新型硫代卡巴肼衍生物的微波促进合成
摘要
微波作为一种有效的热源正广泛应用于化学的各个领域,尤其在有机化学领域。通常在传统加热条件下需要较长回流时间才能完成的反应,在微波促进下能够方便;快速完成。与传统法相比,微波辐射下的有机反应通常具有反应时间短、产率高、产品纯度高、操作简便等优点,因此,微波辐射应用于活化有机反应前景广阔。
硫代卡巴肼的衍生物在医药研究,分析化学等领域有着广泛应用。硫代卡巴肼和它的衍生物还是很好的有机合成中间体。此外,酰氨基硫脲、1,3,4-噻二唑及1,2,4-三唑并[3,4-b]-1,3,4-噻二唑类化合物均具有广泛的生物活性,在医学、农学和生物学等方面具有良好的应用前景。
本论文首先以硫代卡巴肼为起始原料,相转移催化环境友好地合成了硫代卡巴肼衍生物1,5-二酰基硫代卡巴肼,然后分别以硫代卡巴肼或1,5-二酰基硫代卡巴肼作为反应中间体,进一步设计合成了分别含有酰氨基硫脲、1,3,4-噻二唑、1,2,4-三唑并[3,4-b]-1,3,4-噻二唑等活性基团的新型化合物。所有化合物的结构均经IR、MS、~1H NMR和元素分析得到确证,并对实验方法、实验结果和反应的可能机理进行了讨论。
本论文共分为五章:
第一章:绪论.
在简单介绍了硫代卡巴肼合成的基础上,介绍了硫代卡巴肼的性质,概述了硫代卡巴肼在化学合成以及工业中的应用进展。并且概述了微波法在化学合成中的应用进展。
第二章:1,5-二(芳酰氨基硫代甲酰基)硫代卡巴肼类化合物的合成.
在室温下,用PEG-400作相转移催化剂,以酰氯为原料,依次与NH_4SCN、硫代卡巴肼反应,高产率制得了11种新型1,5-二(芳酰氨基硫代甲酰基)硫代卡巴肼类化合物,产品结构经IR、MS、~1H NMR和元素分析得到确证。
第三章:微波促进2-芳基-5-芳酰肼基-1,3,4-噻二唑类化合物的合成.
在室温条件下,以PEG-400为相转移催化剂,硫代卡巴肼直接与酰氯反应合成了一系列1,5-二芳酰基硫代卡巴肼,并进一步在微波辐射条件下以冰醋酸为没环合剂,得到了10种含1,3,4-噻二唑环的新型化合物2-芳基-5-芳酰肼基-1,3,4-噻二唑类化合物。产品结构经IR、MS、~1H NMR和元素分析得到确证。该合成方法是一条环境友好的合成路线,而且还具有反应条件温和、反应时间短、产率高、操作简便等优点。
第四章:微波辐射条件下合成均三唑并[3,4-b]-1,3,4-噻二唑类化合物.
以硅胶支载磷酰氯为脱水剂,通过芳甲酸与硫代卡巴肼在微波辐射条件下的反应一步合成了均三唑并[3,4-b]-1,3,4-噻二唑类化合物,并和常规的方法进行了比较。产品结构经IR、MS、~1H NMR和元素分析得到确证。该法反应时间短,环境友好,是合成均三唑并噻二唑类化合物的一种新颖的途径.
第五章:微波辐射条件下,使用硅胶支载磷酰氯作脱水剂合成1-芳亚甲基-2-(5-芳基-1,3,4-噻二唑-2-基)肼类化合物。
利用固载催化剂SiO_2-OPOCl_2作脱水剂,微波辐射下绿色合成了11种新的1-芳亚甲基-2-(5-芳基-1,3,4-噻二唑-2-基)肼类化合物,产品结构经IR、MS、~1HNMR和元素分析得到确证。
Microwave irradiation as an efficient thermal energy source has become a standard technique in various fields of chemistry, especially in organic chemistry. Synthesis of chemical compounds which normally require long reflux time can be achieved conveniently and very rapidly in a microwave oven. Compared to the classical heating methods, microwave irradiation has the advantages of short reaction time, high yields, pure products and easy workup. The use of microwave energy to activate organic reactions has been taking a new dimension very recently.
Thiocarbohydrazide derivatives are widely used in medicinal research, analytical chemistry and so on. Furthermore, thiocarbohydrazide and its derivatives are important intermediates in organic synthesis. In addition, acylthiosemicarbazides, 1,3,4-thiadiazoles, 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles have extensive biological activities. Therefore they have also been applied to many fields, for instance, medicine, agronomy, biology, etc.
In this thesis, thiocarbohydrazide derivatives, 1, 5-diacyl thiocarbohydrazides were first eco-friendly synthesized using phase transfer catalyst. Then, a series of new compounds and their heterocyclic derivatives were further synthesized using thiocarbohydrazide or 1, 5-diacyl thiocarbohydrazides as intermediates. In all of these new compounds, active groups such as acylthiosemicarbazide, 1,3, 4-thiadiazole, 1, 2, 4-triazolo[3,4-b]-1,3,4-thiadiazole are included respectively. The structures of all compounds were confirmed by IR, ~1H NMR, MS and elemental analysis. The experimental methodologies, results and possible mechanism were also proposed in this thesis.
This thesis includes five chapters:
Chapter 1: Introduction.
In the beginning, synthesis of thiocarbohydrazide was introduced briefly. And then, the properties of thiocarbohydrazide and its applications in chemical synthesis and industry were introduced. Finally, the applied progress of MWI in chemistry synthesis was summarized simply.
Chapter 2: Synthesis of 1, 5-bis(aroyIcarbamothioyI)thiocarbohydrazides.
Eleven new 1, 5-bis(aroylcarbamothioyl)thiocarbohydrazides were synthesized at room temperature under phase transfer catalysis condition in high yield by two-step reactions: a variety of aroyl chlorides first reacted with ammonium thiocyanate, then with thiocarbohydrazide. The structures of all compounds were confirmed by IR, ~1H NMR, MS and elemental analyses.
Chapter 3: Microwave-promoted Synthesis of 2-aryl-5-acylhydrazino-1, 3, 4-thiadiazoles.
Thiocarbohydrazide readily reacted with a variety of aroyl chlorides at room temperature under phase transfer catalysis condition to afford ten 1, 5-diaroylthiocarbohydrazides in high yield. Furthermore, A concise and rapid synthetic route to 2-aryl-5-acylhydrazino-l,3,4-thiadiazoles by the cyclization of 1,5-diaroylthiocarbohydrazides under microwave irradiation is described, and the structures of all compounds were confirmed by IR, ~1H NMR, MS and elemental analyses. This strategy has features of mild condition, short reaction period, and simple work-up procedure.
Chapter 4: Microwave-promoted Synthesis of 3, 6-disubstituted-1, 2, 4-triazolo[3,4-b]-1,3,4-thiadiazoles.
A series of 3, 6-disubstituted-1, 2, 4-triazolo[3,4-b]-1,3,4-thiadiazoles was synthesized under microwave irradiation by one-step reaction: substituted benzoic acid directly reacted with thiocarbohydrazide using silica supported dichlorophosphate as dehydrating agent. The structures of all compounds were confirmed by IR, ~1H NMR, MS and elemental analyses. Compared to the traditional method, this strategy has features of short reaction period, benign to environment and simple work-up procedure.
Chapter 5: Rapid microwave-promoted synthesis of l-arylidene-2-(5-aryl-1, 3,4-thiadiazol- 2-yl)hydrazines.
Eleven new 1-arylidene-2-(5-aryl-1, 3, 4-thiadiazol-2-yl)hydrazines were synthesized under microwave irradiation using silica supported dichlorophosphate as dehydrating agent. The structures of all compounds were confirmed by IR, ~1H NMR, MS and elemental analyses.
硫代卡巴肼的衍生物在医药研究,分析化学等领域有着广泛应用。硫代卡巴肼和它的衍生物还是很好的有机合成中间体。此外,酰氨基硫脲、1,3,4-噻二唑及1,2,4-三唑并[3,4-b]-1,3,4-噻二唑类化合物均具有广泛的生物活性,在医学、农学和生物学等方面具有良好的应用前景。
本论文首先以硫代卡巴肼为起始原料,相转移催化环境友好地合成了硫代卡巴肼衍生物1,5-二酰基硫代卡巴肼,然后分别以硫代卡巴肼或1,5-二酰基硫代卡巴肼作为反应中间体,进一步设计合成了分别含有酰氨基硫脲、1,3,4-噻二唑、1,2,4-三唑并[3,4-b]-1,3,4-噻二唑等活性基团的新型化合物。所有化合物的结构均经IR、MS、~1H NMR和元素分析得到确证,并对实验方法、实验结果和反应的可能机理进行了讨论。
本论文共分为五章:
第一章:绪论.
在简单介绍了硫代卡巴肼合成的基础上,介绍了硫代卡巴肼的性质,概述了硫代卡巴肼在化学合成以及工业中的应用进展。并且概述了微波法在化学合成中的应用进展。
第二章:1,5-二(芳酰氨基硫代甲酰基)硫代卡巴肼类化合物的合成.
在室温下,用PEG-400作相转移催化剂,以酰氯为原料,依次与NH_4SCN、硫代卡巴肼反应,高产率制得了11种新型1,5-二(芳酰氨基硫代甲酰基)硫代卡巴肼类化合物,产品结构经IR、MS、~1H NMR和元素分析得到确证。
第三章:微波促进2-芳基-5-芳酰肼基-1,3,4-噻二唑类化合物的合成.
在室温条件下,以PEG-400为相转移催化剂,硫代卡巴肼直接与酰氯反应合成了一系列1,5-二芳酰基硫代卡巴肼,并进一步在微波辐射条件下以冰醋酸为没环合剂,得到了10种含1,3,4-噻二唑环的新型化合物2-芳基-5-芳酰肼基-1,3,4-噻二唑类化合物。产品结构经IR、MS、~1H NMR和元素分析得到确证。该合成方法是一条环境友好的合成路线,而且还具有反应条件温和、反应时间短、产率高、操作简便等优点。
第四章:微波辐射条件下合成均三唑并[3,4-b]-1,3,4-噻二唑类化合物.
以硅胶支载磷酰氯为脱水剂,通过芳甲酸与硫代卡巴肼在微波辐射条件下的反应一步合成了均三唑并[3,4-b]-1,3,4-噻二唑类化合物,并和常规的方法进行了比较。产品结构经IR、MS、~1H NMR和元素分析得到确证。该法反应时间短,环境友好,是合成均三唑并噻二唑类化合物的一种新颖的途径.
第五章:微波辐射条件下,使用硅胶支载磷酰氯作脱水剂合成1-芳亚甲基-2-(5-芳基-1,3,4-噻二唑-2-基)肼类化合物。
利用固载催化剂SiO_2-OPOCl_2作脱水剂,微波辐射下绿色合成了11种新的1-芳亚甲基-2-(5-芳基-1,3,4-噻二唑-2-基)肼类化合物,产品结构经IR、MS、~1HNMR和元素分析得到确证。
Microwave irradiation as an efficient thermal energy source has become a standard technique in various fields of chemistry, especially in organic chemistry. Synthesis of chemical compounds which normally require long reflux time can be achieved conveniently and very rapidly in a microwave oven. Compared to the classical heating methods, microwave irradiation has the advantages of short reaction time, high yields, pure products and easy workup. The use of microwave energy to activate organic reactions has been taking a new dimension very recently.
Thiocarbohydrazide derivatives are widely used in medicinal research, analytical chemistry and so on. Furthermore, thiocarbohydrazide and its derivatives are important intermediates in organic synthesis. In addition, acylthiosemicarbazides, 1,3,4-thiadiazoles, 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles have extensive biological activities. Therefore they have also been applied to many fields, for instance, medicine, agronomy, biology, etc.
In this thesis, thiocarbohydrazide derivatives, 1, 5-diacyl thiocarbohydrazides were first eco-friendly synthesized using phase transfer catalyst. Then, a series of new compounds and their heterocyclic derivatives were further synthesized using thiocarbohydrazide or 1, 5-diacyl thiocarbohydrazides as intermediates. In all of these new compounds, active groups such as acylthiosemicarbazide, 1,3, 4-thiadiazole, 1, 2, 4-triazolo[3,4-b]-1,3,4-thiadiazole are included respectively. The structures of all compounds were confirmed by IR, ~1H NMR, MS and elemental analysis. The experimental methodologies, results and possible mechanism were also proposed in this thesis.
This thesis includes five chapters:
Chapter 1: Introduction.
In the beginning, synthesis of thiocarbohydrazide was introduced briefly. And then, the properties of thiocarbohydrazide and its applications in chemical synthesis and industry were introduced. Finally, the applied progress of MWI in chemistry synthesis was summarized simply.
Chapter 2: Synthesis of 1, 5-bis(aroyIcarbamothioyI)thiocarbohydrazides.
Eleven new 1, 5-bis(aroylcarbamothioyl)thiocarbohydrazides were synthesized at room temperature under phase transfer catalysis condition in high yield by two-step reactions: a variety of aroyl chlorides first reacted with ammonium thiocyanate, then with thiocarbohydrazide. The structures of all compounds were confirmed by IR, ~1H NMR, MS and elemental analyses.
Chapter 3: Microwave-promoted Synthesis of 2-aryl-5-acylhydrazino-1, 3, 4-thiadiazoles.
Thiocarbohydrazide readily reacted with a variety of aroyl chlorides at room temperature under phase transfer catalysis condition to afford ten 1, 5-diaroylthiocarbohydrazides in high yield. Furthermore, A concise and rapid synthetic route to 2-aryl-5-acylhydrazino-l,3,4-thiadiazoles by the cyclization of 1,5-diaroylthiocarbohydrazides under microwave irradiation is described, and the structures of all compounds were confirmed by IR, ~1H NMR, MS and elemental analyses. This strategy has features of mild condition, short reaction period, and simple work-up procedure.
Chapter 4: Microwave-promoted Synthesis of 3, 6-disubstituted-1, 2, 4-triazolo[3,4-b]-1,3,4-thiadiazoles.
A series of 3, 6-disubstituted-1, 2, 4-triazolo[3,4-b]-1,3,4-thiadiazoles was synthesized under microwave irradiation by one-step reaction: substituted benzoic acid directly reacted with thiocarbohydrazide using silica supported dichlorophosphate as dehydrating agent. The structures of all compounds were confirmed by IR, ~1H NMR, MS and elemental analyses. Compared to the traditional method, this strategy has features of short reaction period, benign to environment and simple work-up procedure.
Chapter 5: Rapid microwave-promoted synthesis of l-arylidene-2-(5-aryl-1, 3,4-thiadiazol- 2-yl)hydrazines.
Eleven new 1-arylidene-2-(5-aryl-1, 3, 4-thiadiazol-2-yl)hydrazines were synthesized under microwave irradiation using silica supported dichlorophosphate as dehydrating agent. The structures of all compounds were confirmed by IR, ~1H NMR, MS and elemental analyses.
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