新型卡巴肼衍生物的绿色合成方法研究
摘要
绿色化学在现代有机合成中有十分重要的应用,近几年来得到了很大的发展。卡巴肼被广泛用作化学除氧剂、金属缓蚀剂、锅炉除垢剂、树脂整理剂、抗氧化剂和固体还原剂,还可用作火箭推进剂的组分和弹性纤维的交联剂等。卡巴肼的衍生物在分析化学、材料科学等领域也有着广泛应用。不仅如此,卡巴肼和它的衍生物还是很好的有机合成中间体。到目前为止,关于卡巴肼衍生物合成的文献报道并不多。本论文以卡巴肼为起始原料,使用无溶剂,水介质,相转移催化,微波辐射等有机合成新技术及新方法设计合成了多类卡巴肼衍生物。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、实验结果和实验的可能机理进行了讨论。
本论文共分为五章:
第一章:文献综述
综述了绿色化学在现代有机合成中的应用,包括溶剂绿色化,选用绿色合成原料,发展催化合成,过程强化,开发新的合成工艺,合成对环境有益的有机化工产品等;还介绍了卡巴肼的物理,化学性质,阐述了卡巴肼的传统和绿色合成方法,并对其化学合成和工业中的应用作了概述。
第二章:无溶剂条件下1,5-二取代卡巴腙的合成
通过“绿色化学品”碳酸二甲酯与水合肼反应首先合成卡巴肼,然后在室温下,采用无溶剂法,使其与芳香醛酮反应,高产率合成了17种1,5-二取代卡巴腙。该法不使用有毒有害的有机溶剂,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。
第三章:微波辐射条件下1,5-二取代卡巴腙与醋酸酐的反应
以1,5-二取代卡巴腙为原料,在醋酸酐溶液中,以微波辐射为反应条件,高产率制得了7种3类1,5-二取代卡巴腙衍生物,分别是噁二唑啉类化合物,2,4-二取代1,5-二取代卡巴腙,1,2-二苄亚甲基肼。
第四章:单取代卡巴腙及其衍生物的微波促进合成
首先,我们以卡巴肼和芳香醛为原料在无溶剂条件下,室温研磨得到了半取代卡巴腙,再以半取代卡巴腙为中间体,在微波辐射条件下,让其与芳香酰氯和芳香硫氰酸脂反应,分别高产率得到了不对称取代脲类衍生物和酰基硫脲类衍生物。该法较传统的液相回流法,反应时间极大的缩短,而且产率也有很大程度的提高。
第五章2,5-二(4'-氨基苯基)-1,3,4-噁二唑衍生物无溶剂和微波促进合成
以2,5-二(4'-氨基苯基)-1,3,4-噁二唑为原料,分别让其在无溶剂、微波、水溶剂条件下与芳香醛酮、芳基酰氯和芳基异硫氰酸脂、芳酰基叠氮化合物反应,生成对应的对称二取代2,5-二(4'-氨基苯基)-1,3,4-噁二唑衍生物。
Green chemistry, which is very important to organic syntheses, has developed very fast recently. Carbohydrazide is widely used as a chemical deoxidant, metal corrosion inhibitor, boiler cleaning medium, resin finishing agent, antioxidant and solid reducing agent. Carbohydrazide is also used as component of propellant and crosslink agent of elastic fibre. Its derivatives have extensive applications in the area of analytic chemistry, material science and so on. Furthermore, carbohydrazide and its derivatives are important intermediates in organic synthesis.
To our best knowledge, there are few literatures that reported the synthesis of the carbohydrazide derivatives. In this thesis, we designed and synthesized some kinds of compounds or derivatives derived from carbohydrazide, under the condition of solvent-free, water media, transfer catalyst, microwave irradiation. 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: Literature Summarize
The principle, conception, contents of research of green chemistry is introduced. Green chemistry is very important to organic syntheses. In order to decrease environmental wastes and realize green syntheses, the following methods are necessary: choose innocuous solvents and green raw material, develop catalyze syntheses, search green chemistry products and other new technology; the development of carbohydrazide in synthesis, properties and applications. And then, we introduced the properties of carbohydrazide, expounded and compared its traditional and "green" preparation methods, and summarized its applications in chemical synthesis and industry.
Chapter 2: Green synthetic method for 1,5-disubstituted carbohydrazons.
Carbohydrazide was first synthesized by reaction of nontoxic "green" reagent, dimethyl carbonate, with hydrazine hydrate. Then carbohydrazide further reacted with various aromatic aldehydes or aliphatic ketones under solvent-free conditions to efficiently afford 1,5-disubstituted carbohydrazone. This eco-friendly strategy no use of organic solvents, high yields, short reaction period, and simple work-up procedure.
Chapter 3: Synthesis of 1, 5-disubstituted carbohydrazons derivatives under microwave irradiation
1, 5-disubstituted carbohydrazons were cylized to afford three kinds 1, 5-disubstituted carbohydrazons derivatives in the presence of Ac_2O under microwave irradiation condition. This method has features of short reaction, high yield and simple work-up procedure.
Chapter 4: Synthesis of Semicarbazone and its derivatives under Microwave Irradiation.
Semicarbazone was synthesized by reations of carbohydrazide and aromatic aldehydes under solvent-free conditions. Recaction of semicarbazone with acyl chlorides or acyl thiocyanate using PEG-400 as catalyst, under microwave irradiation gaves two kinds of semicarbazone derivatives in good to high yield and rapid reaction.
Chapter 5: Green synthesis of 2, 5-Bis (p-aminophenyl)-1, 3, 4-oxadiazole and its derivatives.
2,5-Bis (p-aminophenyl)-1, 3,4-oxadiazole were prepared with p-aminobenzoic acid, hydrazine hydrate and PPA. 2,5-Bis(p-aminophenyl)-1,3,4-oxadiazole were reacted with aldehydes or aliphatic ketones, acyl chlorides and acyl thiocyanate, acyl azides, separately ,under solvent-free, microwave irradiation, water media condition afford four kinds of 2,5-Bis(p-aminophenyl)-1,3,4-oxadiazole derivatives.
本论文共分为五章:
第一章:文献综述
综述了绿色化学在现代有机合成中的应用,包括溶剂绿色化,选用绿色合成原料,发展催化合成,过程强化,开发新的合成工艺,合成对环境有益的有机化工产品等;还介绍了卡巴肼的物理,化学性质,阐述了卡巴肼的传统和绿色合成方法,并对其化学合成和工业中的应用作了概述。
第二章:无溶剂条件下1,5-二取代卡巴腙的合成
通过“绿色化学品”碳酸二甲酯与水合肼反应首先合成卡巴肼,然后在室温下,采用无溶剂法,使其与芳香醛酮反应,高产率合成了17种1,5-二取代卡巴腙。该法不使用有毒有害的有机溶剂,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。
第三章:微波辐射条件下1,5-二取代卡巴腙与醋酸酐的反应
以1,5-二取代卡巴腙为原料,在醋酸酐溶液中,以微波辐射为反应条件,高产率制得了7种3类1,5-二取代卡巴腙衍生物,分别是噁二唑啉类化合物,2,4-二取代1,5-二取代卡巴腙,1,2-二苄亚甲基肼。
第四章:单取代卡巴腙及其衍生物的微波促进合成
首先,我们以卡巴肼和芳香醛为原料在无溶剂条件下,室温研磨得到了半取代卡巴腙,再以半取代卡巴腙为中间体,在微波辐射条件下,让其与芳香酰氯和芳香硫氰酸脂反应,分别高产率得到了不对称取代脲类衍生物和酰基硫脲类衍生物。该法较传统的液相回流法,反应时间极大的缩短,而且产率也有很大程度的提高。
第五章2,5-二(4'-氨基苯基)-1,3,4-噁二唑衍生物无溶剂和微波促进合成
以2,5-二(4'-氨基苯基)-1,3,4-噁二唑为原料,分别让其在无溶剂、微波、水溶剂条件下与芳香醛酮、芳基酰氯和芳基异硫氰酸脂、芳酰基叠氮化合物反应,生成对应的对称二取代2,5-二(4'-氨基苯基)-1,3,4-噁二唑衍生物。
Green chemistry, which is very important to organic syntheses, has developed very fast recently. Carbohydrazide is widely used as a chemical deoxidant, metal corrosion inhibitor, boiler cleaning medium, resin finishing agent, antioxidant and solid reducing agent. Carbohydrazide is also used as component of propellant and crosslink agent of elastic fibre. Its derivatives have extensive applications in the area of analytic chemistry, material science and so on. Furthermore, carbohydrazide and its derivatives are important intermediates in organic synthesis.
To our best knowledge, there are few literatures that reported the synthesis of the carbohydrazide derivatives. In this thesis, we designed and synthesized some kinds of compounds or derivatives derived from carbohydrazide, under the condition of solvent-free, water media, transfer catalyst, microwave irradiation. 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: Literature Summarize
The principle, conception, contents of research of green chemistry is introduced. Green chemistry is very important to organic syntheses. In order to decrease environmental wastes and realize green syntheses, the following methods are necessary: choose innocuous solvents and green raw material, develop catalyze syntheses, search green chemistry products and other new technology; the development of carbohydrazide in synthesis, properties and applications. And then, we introduced the properties of carbohydrazide, expounded and compared its traditional and "green" preparation methods, and summarized its applications in chemical synthesis and industry.
Chapter 2: Green synthetic method for 1,5-disubstituted carbohydrazons.
Carbohydrazide was first synthesized by reaction of nontoxic "green" reagent, dimethyl carbonate, with hydrazine hydrate. Then carbohydrazide further reacted with various aromatic aldehydes or aliphatic ketones under solvent-free conditions to efficiently afford 1,5-disubstituted carbohydrazone. This eco-friendly strategy no use of organic solvents, high yields, short reaction period, and simple work-up procedure.
Chapter 3: Synthesis of 1, 5-disubstituted carbohydrazons derivatives under microwave irradiation
1, 5-disubstituted carbohydrazons were cylized to afford three kinds 1, 5-disubstituted carbohydrazons derivatives in the presence of Ac_2O under microwave irradiation condition. This method has features of short reaction, high yield and simple work-up procedure.
Chapter 4: Synthesis of Semicarbazone and its derivatives under Microwave Irradiation.
Semicarbazone was synthesized by reations of carbohydrazide and aromatic aldehydes under solvent-free conditions. Recaction of semicarbazone with acyl chlorides or acyl thiocyanate using PEG-400 as catalyst, under microwave irradiation gaves two kinds of semicarbazone derivatives in good to high yield and rapid reaction.
Chapter 5: Green synthesis of 2, 5-Bis (p-aminophenyl)-1, 3, 4-oxadiazole and its derivatives.
2,5-Bis (p-aminophenyl)-1, 3,4-oxadiazole were prepared with p-aminobenzoic acid, hydrazine hydrate and PPA. 2,5-Bis(p-aminophenyl)-1,3,4-oxadiazole were reacted with aldehydes or aliphatic ketones, acyl chlorides and acyl thiocyanate, acyl azides, separately ,under solvent-free, microwave irradiation, water media condition afford four kinds of 2,5-Bis(p-aminophenyl)-1,3,4-oxadiazole derivatives.
引文
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