一些5-甲基-1-芳基-4-取代甲基-1H-1，2，3-三唑衍生物的合成与研究
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摘要
迄今为止，大量的文献报道了1H-1，2，3-三唑衍生物是一类具有广泛生物活性的化合物，它们被广泛应用在工业、农业、医学等领域。所以，由于它们的这些广泛应用，使得这类芳香杂环越来越引起人们的注意，新的化合物不断地被合成出来并持续到现在。基于此并为了获得新型的生物活性试剂，我们在这些领域开展了几个系列衍生物的合成研究和探讨。
1H-1，2，3-三唑类化合物因其具有广泛的生物活性使其在医疗领域应用颇多。最近几年来，不断有新的此类化合物被合成出来，它们所具有的生物活性也得到测定和证实。为了寻找到新的生物活性更好的试剂，本文设计合成了三个系列的化合物，并在1H-1，2，3-三唑衍生物中引入咪唑基，氮丙啶基等含氮基团并对其中的两个系列中的两个化合物进行了生物活性测定。所有新化合物均用~1HNMR、IR、MS谱表征了结构，其中三个化合物用单晶X光衍射法测定了其结构。
本文总共合成了27个新的1H-1，2，3-三唑类化合物，我们以芳香胺为起始原料，合成5-甲基-1-芳基-1H-1，2，3-三唑-4-甲酸乙酯，与格氏试剂反应合成(5-甲基-1-芳基-1H-1，2，3-三唑-4-基)-二芳基甲醇，然后在此基础上经过两步反应，通过两种不同的合成方法合成了两个系列的1H-1，2，3-三唑类衍生物5-甲基-1-芳基-4-[(1H-咪唑-1-基)二芳基甲基]-1H-1，2，3-三唑和5-甲基-1-芳基-4-[(氮丙啶-1-基)二芳基甲基]-1H-1，2，3-三唑。在合成和收率方面，两种方法各有优缺点。另外，我们用单晶X光衍射法对二(3-氯苯基)-(5-甲基-1-对甲苯基-1H-1，2，3-三唑-4-基)甲醇、5-甲基-1-苯基-4-[(1H-咪唑-1-基)二苯基甲基]-1H-1，2，3-三唑和5-甲基-1-苯基-4-[(氮丙啶-1-基)二苯基甲基]-1H-1，2，3-三唑进行了晶体结构测定。
为了了解我们所合成的这些化合物的生物活性，我们挑选5-甲基-1-对氯苯基-4-[(1H-咪唑-1-基)二对氯苯基甲基]-1H-1，2，3-三唑和5-甲基-1-对甲苯基-4-[(氮丙啶-1-基)二苯基甲基]-1H-1，2，3-三唑两个化合物进行了生物活性的测定。
Up to now, it has been reported that 1H-1,2,3-triazoles and their derivatives are one type of compounds which have extensive biological activities by numerous literatures. They are widely used in industry, agriculture, medicine and so on. Therefore, this kind of aromatic heterocycles is getting more and more attention due to their extensively application and new compounds were synthesized constantly till now. Because of the above truth and in order to obtain new biologically active compounds, We have worked on synthesis and inquirement of some series of 1H-1,2,3-triazole derivatives in the field.
1H-1,2,3-triazoles are primarily used in medicine because of their extensive biological activities. In recent years, new compounds were synthesized continually and their biological activities were determined and proved. In order to look for new biological activities, we designed and synthesized three series of compounds in this thesis. In these compounds, we introduced functional group such as imidazole and aziridine group. Moreover, we determined biological activities of two compounds in two series. All compounds' structures were determined by ~1HNMR, IR and MS. The crystalline structures of three compounds were determined by x-ray diffraction method.
In this thesis, it is descripted that new twenty-seven compounds are synthesized. Ethyl 1-aryl- 5-methyl-1H-1,2,3-triazole-4-carboxylate derivatives were synthesized from aromatic amine. (1-Aryl-5-methyl-1H-1,2,3-triazol-4-yl)diarylmethanol were obtained by the reaction of ethyl 1-aryl-5-methyl-1H-1,2,3-triazole-4-carboxylate derivatives with aryl Grignard reagents. We synthesized two series of 1H-1,2,3 -triazole derivatives by two different methods. In the synthesis method and yield, the advantage and disadvantage of two methods have respectively exhibited. Besides, the structures of bis(3-chlorophenyl)(5-methyl-1-p-tolyl-1H-1,2,3-triazol- 4-yl)methanol, 5-methyl-1-phenyl-4-[diphenyl(1H-imidazol-1 -yl)methyl]-1H-1,2,3-triazole and 4-[(a ziridin-1-yl)diphenylmethyl]-5-methyl-1-p-tolyl-1H-1,2,3-triazole were determined by x-ray diffraction method.
In order to look for the biological activities of compounds we synthesized, we choice 4- [bis(4-chlorophenyl)(1H-imidazol-1 -yl)methyl] -1 -(4-chlorophenyl)-5 -methyl- 1H-1,2,3-triazole and 4-[(aziridin-1 -yl)diphenylmethyl]-5-methyl-1-p-tolyl-1H-1,2, 3-triazo- le and determined their biological activities.
1H-1，2，3-三唑类化合物因其具有广泛的生物活性使其在医疗领域应用颇多。最近几年来，不断有新的此类化合物被合成出来，它们所具有的生物活性也得到测定和证实。为了寻找到新的生物活性更好的试剂，本文设计合成了三个系列的化合物，并在1H-1，2，3-三唑衍生物中引入咪唑基，氮丙啶基等含氮基团并对其中的两个系列中的两个化合物进行了生物活性测定。所有新化合物均用~1HNMR、IR、MS谱表征了结构，其中三个化合物用单晶X光衍射法测定了其结构。
本文总共合成了27个新的1H-1，2，3-三唑类化合物，我们以芳香胺为起始原料，合成5-甲基-1-芳基-1H-1，2，3-三唑-4-甲酸乙酯，与格氏试剂反应合成(5-甲基-1-芳基-1H-1，2，3-三唑-4-基)-二芳基甲醇，然后在此基础上经过两步反应，通过两种不同的合成方法合成了两个系列的1H-1，2，3-三唑类衍生物5-甲基-1-芳基-4-[(1H-咪唑-1-基)二芳基甲基]-1H-1，2，3-三唑和5-甲基-1-芳基-4-[(氮丙啶-1-基)二芳基甲基]-1H-1，2，3-三唑。在合成和收率方面，两种方法各有优缺点。另外，我们用单晶X光衍射法对二(3-氯苯基)-(5-甲基-1-对甲苯基-1H-1，2，3-三唑-4-基)甲醇、5-甲基-1-苯基-4-[(1H-咪唑-1-基)二苯基甲基]-1H-1，2，3-三唑和5-甲基-1-苯基-4-[(氮丙啶-1-基)二苯基甲基]-1H-1，2，3-三唑进行了晶体结构测定。
为了了解我们所合成的这些化合物的生物活性，我们挑选5-甲基-1-对氯苯基-4-[(1H-咪唑-1-基)二对氯苯基甲基]-1H-1，2，3-三唑和5-甲基-1-对甲苯基-4-[(氮丙啶-1-基)二苯基甲基]-1H-1，2，3-三唑两个化合物进行了生物活性的测定。
Up to now, it has been reported that 1H-1,2,3-triazoles and their derivatives are one type of compounds which have extensive biological activities by numerous literatures. They are widely used in industry, agriculture, medicine and so on. Therefore, this kind of aromatic heterocycles is getting more and more attention due to their extensively application and new compounds were synthesized constantly till now. Because of the above truth and in order to obtain new biologically active compounds, We have worked on synthesis and inquirement of some series of 1H-1,2,3-triazole derivatives in the field.
1H-1,2,3-triazoles are primarily used in medicine because of their extensive biological activities. In recent years, new compounds were synthesized continually and their biological activities were determined and proved. In order to look for new biological activities, we designed and synthesized three series of compounds in this thesis. In these compounds, we introduced functional group such as imidazole and aziridine group. Moreover, we determined biological activities of two compounds in two series. All compounds' structures were determined by ~1HNMR, IR and MS. The crystalline structures of three compounds were determined by x-ray diffraction method.
In this thesis, it is descripted that new twenty-seven compounds are synthesized. Ethyl 1-aryl- 5-methyl-1H-1,2,3-triazole-4-carboxylate derivatives were synthesized from aromatic amine. (1-Aryl-5-methyl-1H-1,2,3-triazol-4-yl)diarylmethanol were obtained by the reaction of ethyl 1-aryl-5-methyl-1H-1,2,3-triazole-4-carboxylate derivatives with aryl Grignard reagents. We synthesized two series of 1H-1,2,3 -triazole derivatives by two different methods. In the synthesis method and yield, the advantage and disadvantage of two methods have respectively exhibited. Besides, the structures of bis(3-chlorophenyl)(5-methyl-1-p-tolyl-1H-1,2,3-triazol- 4-yl)methanol, 5-methyl-1-phenyl-4-[diphenyl(1H-imidazol-1 -yl)methyl]-1H-1,2,3-triazole and 4-[(a ziridin-1-yl)diphenylmethyl]-5-methyl-1-p-tolyl-1H-1,2,3-triazole were determined by x-ray diffraction method.
In order to look for the biological activities of compounds we synthesized, we choice 4- [bis(4-chlorophenyl)(1H-imidazol-1 -yl)methyl] -1 -(4-chlorophenyl)-5 -methyl- 1H-1,2,3-triazole and 4-[(aziridin-1 -yl)diphenylmethyl]-5-methyl-1-p-tolyl-1H-1,2, 3-triazo- le and determined their biological activities.
引文
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5．上海第二制药厂，医药工业，No．3，5-9，1973．