2-芳甲酰亚胺基-3-芳基-1，3-噻唑啉衍生物的合成研究
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摘要
众所周知，大部分有机反应是在有机溶剂中进行的，而大多数有机溶剂易燃、易挥发、有毒，且废液无论是回收还是排放都会对环境造成一定的污染。随着人们对生存环境的日益重视，以水作为溶剂的有机反应的研究越来越受到人们的关注，这是由于水作为反应介质，具有价廉、易得、不可燃、无污染等优点，具有有机溶剂无可取代的优越性。
另外，对微波辐射无溶剂有机反应的研究也具有重要的理论和实践意义。微波辐射无溶剂反应，由于反应中没有溶剂分子的参与，反应在固态下进行，反应物的局部浓度提高和反应分子的有序排列增加了反应速率，提高了反应的选择性和收率。同时，微波辐射下的无溶剂有机反应具有操作简单、无有机溶剂污染等优点，是一种较理想的合成方法。
综上所述，在水介质中合成和微波辐射无溶剂合成目标化合物，是绿色化学的思路，符合绿色合成的要求，基本解决了合成中使用有机溶剂对环境造成的污染问题。
本论文共分两大部分：
第一部分：2-芳甲酰亚胺基-3-芳基-4-甲基／苯基-1，3-噻唑啉衍生物的合成。
系列Ⅰ：首先合成关键中间体N-芳基-N’-苯甲酰基硫脲，以此中间体为原料，回流条件下分别与α-溴代丙酮、α-溴代苯乙酮反应，合成了12种新型的2-苯甲酰亚胺基-3-芳基-4-甲基／苯基-1，3-噻唑啉化合物(2a～21)。
系列Ⅱ：以5-芳基-2-呋喃甲酰氯为原料，在水溶液中与硫氰酸铵、芳胺在苄基三乙基氯化铵(TEBA)存在条件下反应，合成中间体N-芳基-N’-(5-芳基-2-呋喃甲酰基)硫脲，此中间体不经分离直接与α-溴代丙酮或α-溴代苯乙酮反应，合成了22种新型的2-(5-芳基-2-呋喃甲酰亚胺基)-3-芳基-4-甲基／苯基-1，3-噻唑啉化合物(Ⅳ～Ⅴ)。此法与传统方法相比较具有反应条件温和、反应时间短、操作简单、无污染等诸多优点。
系列Ⅲ：首先合成关键中间体N-芳基-N’-(2-苯并呋喃甲酰基)硫脲，以此中间体为原料，在微波辐射Al_2O_3支载条件下分别与α-溴代丙酮、α-溴代苯乙酮反应，合成了20种新型2-(2-苯并呋喃甲酰亚胺基)-3-芳基-4-甲基／苯基-1，3-噻唑啉化合物(4a～4t)，产物的结构和反应机理得到了单晶X射线衍射实验的证实。并分别考察了原料配比、微波辐射功率和辐射时间等多种因素对反应的影响，从而优选出了最佳反应条件。
第二部分：N-芳基-2-苯并呋喃甲酰胺和N，N’-二芳基-2-硝基-1，4-苯二氧基二乙酰胺的绿色合成。
系列Ⅲ_1～Ⅲ_(13)：在无溶剂微波辐射条件下，2-苯并呋喃甲酰氯和等当量的各种芳胺快速定量地反应得到N-芳基-2-苯并呋喃甲酰胺。系列Ⅳ_1～Ⅳ_(12)：在无溶剂条件下，2-硝基-1，4-苯二氧基二乙酰氯与两倍当量的各种芳胺在室温下研磨反应得到N，N’-二芳基-2-硝基-1，4-苯二氧基二乙酰胺。这些方法与传统溶液法相比具有无有机溶剂污染、反应速度快、产率高和后处理简单等诸多优点。
用元素分析、红外光谱、核磁共振氢谱和碳谱表征了以上几个系列化合物的结构，并对波谱数据进行了分析。
It is well known that the typical organic synthesis has been carried out in organic solvents. However, most of organic solvents are flammable, volatile and toxic. Recently years, with the increasing concern on the environmental of human being lived, the use of water as a medium in organic reaction has received considerable attention due to its several advantages, for example, it is cheaper, nonflammable, nontoxic and easily available on the earth, and had incommutable advantages relative to organic solvents.
Combination of microwave irradiation and solvent-free strategy in organic reaction has attracted many interests in chemical industry. Indeed, most of solvent-free organic reactions occurred in solid state, the tightly and regularly arranged structures of solids made the reactions proceed more efficiently and selectively than solution ones. Furthermore, organic reactions promoted by microwave under solvent-free condition have advantages of avoiding the use of organic solvents, is clean, effective and economical, in which the safety is largely increased, workup procedure is considerably simplified and the cost is greatly reduced.
In summary, the aqueous media route and the microwave irradiation solvent-free design were all based on the green-chemistry and avoided the pollution of environment.
Part I: Green synthesis of 2-acylimino-3-aryl-4-methyl/phenyl-1,3-thiazoline derivatives.
Series I: 12 New 2-benzoylimino-3-aryl-4-methyl/phenyl-1,3-thiazoline derivatives 2a～2I were synthesized by condensation reaction of N-aryl-N'-benzoyl thioureas withα-bromoacetone andα-bromoacetophenone under refluxing.
Series II: The one-pot two-step synthesis for 22 new 2-(5-aryl-2-furoylimino)-3-aryl -4-methyl/phenyl-1,3-thiazoline derivatives IV～V by treatment of N-aryl-N'(5-aryl-2-furoyl) thiourea withα-bromoacetone andα-bromoacetophenone under aqueous media. The intermediate thiourea obtained from reactions of 5-aryl-2-furoyl chloride with ammonium thiocyanate and arylamines in the presence of benzyltriethylammonium chloride (TEBA) as catalyst in H_2O at room temperature and without isolation. Compared to classical reaction in organic solvents, this method consistently has the advantage of short reaction times, simple work-up procedure and environmentally friendly.
Series III: 20 New 2-(2-benzofuroylimino)-3-aryl-4-methyl/phenyl-1,3-thiazoline derivatives 4a～4t were synthesized by condensation reaction of N-aryl-N'-(2-benzofuroyl) thiourea withα-bromoacetone andα-bromoacetophenone on alumina using microwave irradiation. The structure of the compounds and the reaction mechanism were supported by X-ray crystal structure analysis. We studied different affects of varies conditions (such as, ratios, irradiation power and time) on the reactions.
Part II: Green synthesis of N-aryl-2-benzofuran amides and N, N -diaryl-2-nitro-1,4-phenylenedioxydiacetamides.
The reactions of 2-benzofurancarbonyl chloride with equivalent of various arylamines under the condition of solventless and microwave irradiation expeditiously gained seriesⅢ_1-Ⅲ_(13). The reactions of N,N'-diaryl-2-nitro-1,4-phenylenedioxydiacetyl chloride with 2 eq. of various arylamines by grinding under solventless and room-temperature conditions expeditiously afforded series IV_1～IV_(12). These synthetic strategies compared with traditional solution protocol have the advantages of no organic solvent pollution, elevated reaction rate, high yield and simple work-up procedure.
The structures of all compounds were confirmed by elemental analysis, IR, ~1H NMR and ~(13)C NMR.
另外，对微波辐射无溶剂有机反应的研究也具有重要的理论和实践意义。微波辐射无溶剂反应，由于反应中没有溶剂分子的参与，反应在固态下进行，反应物的局部浓度提高和反应分子的有序排列增加了反应速率，提高了反应的选择性和收率。同时，微波辐射下的无溶剂有机反应具有操作简单、无有机溶剂污染等优点，是一种较理想的合成方法。
综上所述，在水介质中合成和微波辐射无溶剂合成目标化合物，是绿色化学的思路，符合绿色合成的要求，基本解决了合成中使用有机溶剂对环境造成的污染问题。
本论文共分两大部分：
第一部分：2-芳甲酰亚胺基-3-芳基-4-甲基／苯基-1，3-噻唑啉衍生物的合成。
系列Ⅰ：首先合成关键中间体N-芳基-N’-苯甲酰基硫脲，以此中间体为原料，回流条件下分别与α-溴代丙酮、α-溴代苯乙酮反应，合成了12种新型的2-苯甲酰亚胺基-3-芳基-4-甲基／苯基-1，3-噻唑啉化合物(2a～21)。
系列Ⅱ：以5-芳基-2-呋喃甲酰氯为原料，在水溶液中与硫氰酸铵、芳胺在苄基三乙基氯化铵(TEBA)存在条件下反应，合成中间体N-芳基-N’-(5-芳基-2-呋喃甲酰基)硫脲，此中间体不经分离直接与α-溴代丙酮或α-溴代苯乙酮反应，合成了22种新型的2-(5-芳基-2-呋喃甲酰亚胺基)-3-芳基-4-甲基／苯基-1，3-噻唑啉化合物(Ⅳ～Ⅴ)。此法与传统方法相比较具有反应条件温和、反应时间短、操作简单、无污染等诸多优点。
系列Ⅲ：首先合成关键中间体N-芳基-N’-(2-苯并呋喃甲酰基)硫脲，以此中间体为原料，在微波辐射Al_2O_3支载条件下分别与α-溴代丙酮、α-溴代苯乙酮反应，合成了20种新型2-(2-苯并呋喃甲酰亚胺基)-3-芳基-4-甲基／苯基-1，3-噻唑啉化合物(4a～4t)，产物的结构和反应机理得到了单晶X射线衍射实验的证实。并分别考察了原料配比、微波辐射功率和辐射时间等多种因素对反应的影响，从而优选出了最佳反应条件。
第二部分：N-芳基-2-苯并呋喃甲酰胺和N，N’-二芳基-2-硝基-1，4-苯二氧基二乙酰胺的绿色合成。
系列Ⅲ_1～Ⅲ_(13)：在无溶剂微波辐射条件下，2-苯并呋喃甲酰氯和等当量的各种芳胺快速定量地反应得到N-芳基-2-苯并呋喃甲酰胺。系列Ⅳ_1～Ⅳ_(12)：在无溶剂条件下，2-硝基-1，4-苯二氧基二乙酰氯与两倍当量的各种芳胺在室温下研磨反应得到N，N’-二芳基-2-硝基-1，4-苯二氧基二乙酰胺。这些方法与传统溶液法相比具有无有机溶剂污染、反应速度快、产率高和后处理简单等诸多优点。
用元素分析、红外光谱、核磁共振氢谱和碳谱表征了以上几个系列化合物的结构，并对波谱数据进行了分析。
It is well known that the typical organic synthesis has been carried out in organic solvents. However, most of organic solvents are flammable, volatile and toxic. Recently years, with the increasing concern on the environmental of human being lived, the use of water as a medium in organic reaction has received considerable attention due to its several advantages, for example, it is cheaper, nonflammable, nontoxic and easily available on the earth, and had incommutable advantages relative to organic solvents.
Combination of microwave irradiation and solvent-free strategy in organic reaction has attracted many interests in chemical industry. Indeed, most of solvent-free organic reactions occurred in solid state, the tightly and regularly arranged structures of solids made the reactions proceed more efficiently and selectively than solution ones. Furthermore, organic reactions promoted by microwave under solvent-free condition have advantages of avoiding the use of organic solvents, is clean, effective and economical, in which the safety is largely increased, workup procedure is considerably simplified and the cost is greatly reduced.
In summary, the aqueous media route and the microwave irradiation solvent-free design were all based on the green-chemistry and avoided the pollution of environment.
Part I: Green synthesis of 2-acylimino-3-aryl-4-methyl/phenyl-1,3-thiazoline derivatives.
Series I: 12 New 2-benzoylimino-3-aryl-4-methyl/phenyl-1,3-thiazoline derivatives 2a～2I were synthesized by condensation reaction of N-aryl-N'-benzoyl thioureas withα-bromoacetone andα-bromoacetophenone under refluxing.
Series II: The one-pot two-step synthesis for 22 new 2-(5-aryl-2-furoylimino)-3-aryl -4-methyl/phenyl-1,3-thiazoline derivatives IV～V by treatment of N-aryl-N'(5-aryl-2-furoyl) thiourea withα-bromoacetone andα-bromoacetophenone under aqueous media. The intermediate thiourea obtained from reactions of 5-aryl-2-furoyl chloride with ammonium thiocyanate and arylamines in the presence of benzyltriethylammonium chloride (TEBA) as catalyst in H_2O at room temperature and without isolation. Compared to classical reaction in organic solvents, this method consistently has the advantage of short reaction times, simple work-up procedure and environmentally friendly.
Series III: 20 New 2-(2-benzofuroylimino)-3-aryl-4-methyl/phenyl-1,3-thiazoline derivatives 4a～4t were synthesized by condensation reaction of N-aryl-N'-(2-benzofuroyl) thiourea withα-bromoacetone andα-bromoacetophenone on alumina using microwave irradiation. The structure of the compounds and the reaction mechanism were supported by X-ray crystal structure analysis. We studied different affects of varies conditions (such as, ratios, irradiation power and time) on the reactions.
Part II: Green synthesis of N-aryl-2-benzofuran amides and N, N -diaryl-2-nitro-1,4-phenylenedioxydiacetamides.
The reactions of 2-benzofurancarbonyl chloride with equivalent of various arylamines under the condition of solventless and microwave irradiation expeditiously gained seriesⅢ_1-Ⅲ_(13). The reactions of N,N'-diaryl-2-nitro-1,4-phenylenedioxydiacetyl chloride with 2 eq. of various arylamines by grinding under solventless and room-temperature conditions expeditiously afforded series IV_1～IV_(12). These synthetic strategies compared with traditional solution protocol have the advantages of no organic solvent pollution, elevated reaction rate, high yield and simple work-up procedure.
The structures of all compounds were confirmed by elemental analysis, IR, ~1H NMR and ~(13)C NMR.
引文
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