[1]刘玉婷,王龙瑞,尹大伟,等.基于肉桂醛的咪唑并[2,1-b]-1,3,4-二唑Mannich碱的合成及表征[J].江西师范大学学报(自然科学版),2021,(01):75-81.[doi:10.16357/j.cnki.issn1000-5862.2021.01.11]
　LIU Yuting,WANG Longrui,YIN Dawei,et al.The Synthesis and Characterization of Imidazo[2,1-b]-1,3,4-Oxadiazole Mannich Bases Based on Cinnamyl Aldehyde[J].Journal of Jiangxi Normal University:Natural Science Edition,2021,(01):75-81.[doi:10.16357/j.cnki.issn1000-5862.2021.01.11]
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基于肉桂醛的咪唑并[2,1-b]-1,3,4-二唑Mannich碱的合成及表征()
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《江西师范大学学报》（自然科学版）[ISSN:1006-6977/CN:61-1281/TN]

卷:
期数:
2021年01期
页码:
75-81
栏目:
出版日期:
2021-02-10

文章信息/Info

Title:
The Synthesis and Characterization of Imidazo[2,1-b]-1,3,4-Oxadiazole Mannich Bases Based on Cinnamyl Aldehyde
文章编号:
1000-5862(2021)01-0075-07
作者:
刘玉婷; 王龙瑞; 尹大伟; 李 洁; 孙嘉希
陕西科技大学化学与化工学院,中国轻工业轻化工助剂重点实验室,陕西 西安 710021
Author(s):
LIU Yuting; WANG Longrui; YIN Dawei; LI Jie; SUN Jiaxi
Key Laboratory of Chemical Additives for China National Light Industry,College of Chemistry and Chemical Engineering, Shaanxi University of Science and Technology,Shaanxi Xi’an 710021,China
关键词:
肉桂醛;  咪唑并[2; 1-b]-1; 3; 4-二唑;  ɑ-溴乙酰基芳酮;  Mannich 碱;  合成
Keywords:
cinnamyl aldehyde;  imidazo[2; 1-b]-1; 3; 4-oxadiazole;  ɑ-bromine-arylacetophenone;  Mannich base;  synthesis
分类号:
TQ 252.3
DOI:
10.16357/j.cnki.issn1000-5862.2021.01.11
文献标志码:
A
摘要:
以肉桂醛与氨基脲经缩合、环合得到2-氨基-5-苯乙烯基-1,3,4-二唑,再与ɑ-溴苯乙酮反应得到2-苯乙烯基-6-芳基咪唑并[2,1-b]-1,3,4-二唑,最后经Mannich反应得到 Mannich碱.所有中间体及产物的结构经IR、1H NMR、ESI-MS及元素分析确证,同时优化了中间体及产物的反应条件.2-苯乙烯基-6-芳基咪唑并[2,1-b]-1,3,4-二唑的最佳反应条件为n(2-氨基-5-苯乙烯基-1,3,4-二唑):n(α-溴代苯乙酮)=1.0:1.2.在浓盐酸催化下于无水乙醇中回流反应18 h,产率为57.8%.Mannich 碱的最佳反应条件为n(2-苯乙烯基-6-芳基咪唑并[2,1-b]-1,3,4-二唑):n(40%甲醛):n(无水哌嗪)=1.0:1.3:1.3,在无水乙醇中回流反应8 h,产率为55.4%.
Abstract:
2-amino-5-styryl-1,3,4-oxadiazole and 2-styryl-6-arylimidazo[2,1-b]-1,3,4-oxadiazole are synthesized by condensation,cyclization of cinnamyl aldehyde with semicarbazide and then with ɑ-bromine-acetophenone.Finally,Mannich bases are synthesized by Mannich reaction.All the intermediates and target products are characterized by IR,1H NMR,ESI-MS and elemental analysis.The reaction condition of intermediates and product are optimized.The optimal condition for synthesis of 2-styryl-6-arylimidazo[2,1-b]-1,3,4-oxadiazole is n(2-amino-5-styryl-1,3,4-oxadiazole):n(ɑ-bromine-acetophenone)=1.0:1.2,refluxed for 18 h in absolute C2H5OH,the yield is above 57.8%.The optimal condition for synthesis of Mannich base is n(2-styryl-6-arylimidazo[2,1-b]-1,3,4-oxadiazole):n(40%formaldahyde):n(absolute piperazine)=1.0:1.3:1.3,catalyzed by concentrated.HCl and refluxed for 8 h,the yield is above 55.4%.

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备注/Memo

备注/Memo:
收稿日期:2020-03-18
基金项目:国家自然科学基金(21706152),陕西省自然科学基础研究计划(面上)课题(2018JM7046)和陕西省教育厅专项课题(18JK0954)资助项目.
作者简介:刘玉婷(1971-),女,陕西富平人,教授,博士,主要从事有机合成研究.E-mail:lyt@sust.edu.cn
更新日期/Last Update: 2021-04-10