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[1]巨修练,胡成.1,3,4噁二唑2硫酮衍生物的合成及工艺[J].武汉工程大学学报,2014,(02):6-10.[doi:103969/jissn16742869201402002]
　JU Xiu lian,HU Cheng.Synthesis of 1,3,4oxadiazole2thione derivatives[J].Journal of Wuhan Institute of Technology,2014,(02):6-10.[doi:103969/jissn16742869201402002]
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1,3,4噁二唑2硫酮衍生物的合成及工艺(/HTML)
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《武汉工程大学学报》[ISSN:1674-2869/CN:42-1779/TQ]

卷:
期数:
2014年02期
页码:
6-10
栏目:
化学与化学工程
出版日期:
2014-02-28

文章信息/Info

Title:
Synthesis of 1,3,4oxadiazole2thione derivatives
文章编号:
16742869(2014)02000605
作者:
巨修练1; 2; 胡成1; 2
1.武汉工程大学化工与制药学院，湖北 武汉 430074；2.绿色化工过程教育部重点实验室（武汉工程大学），湖北 武汉 430074\
Author(s):
JU Xiulian1; 2; HU Cheng1; 2
1．School of Chemical Engineering and Pharmacy,Wuhan Institute of Technology,Wuhan 430074，China；2．Key Laboratory for Green Chemical Process of Ministry of Education(Wuhan Institute of Technology),Wuhan 430074，China\
关键词:
杂环化合物; 1; 3; 4噁二唑2硫酮; 结构表征; 工艺优化
Keywords:
heterocyclic compounds;  1; 3; 4oxadiazole2thione;  structural characterization;  process optimization
分类号:
O621.3
DOI:
103969/jissn16742869201402002
文献标志码:
A
摘要:
噁二唑类化合物是一类具有广泛生物活性的杂环化合物，具有高效，低毒等优点. 设计合成了4a~4g 7个1,3,4噁二唑2硫酮衍生物并经过核磁共振氢谱和质谱进行结构表征和确认. 以苯甲酸甲酯(1)为起始原料与水合肼加热回流反应得到苯甲酰肼(2)，然后与二硫化碳在碱性条件下回流合环生成中间体5苯基1,3,4噁二唑2硫酮(3)，最后与一系列取代苯胺和甲醛发生曼尼希反应得到目标化合物. 实验过程中对反应(a)中反应时间和80%水合肼与苯甲酸甲酯(1)的摩尔比，反应(b)中反应时间和二硫化碳与苯甲酰肼的摩尔比，反应(c)中溶剂的选用等参数进行了工艺优化. 以适当溶剂重结晶均得到纯的目标化合物，收率在20%~80%. 大部分目标化合物是未见文献报道的新化合物，其作为酪氨酸酶抑制剂的生物活性有待进一步研究.
Abstract:
Oxadiazole derivatives as heterocyclic compounds have shown a broad range of biological activities.Seven 1,3,4oxadiazole2thione derivatives were designed and synthesized,and all of them were characterized and confirmed by 1H NMR and mass spectrometry.Benzoyl hydrazine (2) was obtained by the reaction of benzoate methyl ester (1) and hydrazine hydrate under refluxing,then 5phenyl1,3,4oxadiazole2thione (3) was obtained by the reaction of benzoyl hydrazine (2) and CS2 in alkaline condition under reflux.Finally target compounds were obtained by Mannich reaction consisting of (3) condensation with amine in the presence of formaldehyde.In the process,the technology is optimized based on some parameters:reaction time,molar ratio of 80% hydrazine hydrate and benzoate methyl ester (1),molar ratio of CS2 and benzoyl hydrazine (2) in reaction (a) and (b) respectively,the use of solvent in reaction (c).Pure target compounds were obtained by recrystallization from suitable solvent,the yields of which were between 20%-80%.Most of the compounds haven’t been reported yet,and their bioactivities as tyrosinase inhibitors remain further study.

参考文献/References:

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备注/Memo

备注/Memo:
本文编辑：张瑞收稿日期：20131217作者简介：巨修练（1959），男，陕西乾县人，教授，博士，博士研究生导师. 研究方向：药物构效关系.
更新日期/Last Update: 2014-03-20