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[1]张 琪,陶世鹏,马 姗,等.新型异喹啉衍生物的合成[J].武汉工程大学学报,2016,38(4):327-328.[doi:10. 3969/j. issn. 1674?2869. 2016. 04. 003]
 ZHANG Qi,TAO Shipeng,MA Shan,et al.Synthesis of Novel Isoquinoline Derivative[J].Journal of Wuhan Institute of Technology,2016,38(4):327-328.[doi:10. 3969/j. issn. 1674?2869. 2016. 04. 003]
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《武汉工程大学学报》[ISSN:1674-2869/CN:42-1779/TQ]

卷:
38
期数:
2016年4期
页码:
327-328
栏目:
化学与化学工程
出版日期:
2016-08-28

文章信息/Info

Title:
Synthesis of Novel Isoquinoline Derivative
作者:
张 琪12陶世鹏23 马 姗12陈云峰13*
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;3. 武汉工程大学化学与环境工程学院,湖北 武汉 430074
Author(s):
ZHANG Qi12TAO Shipeng23 MA Shan12 CHEN Yunfeng13*
1. School of Chemical Engineering and Pharmacy, Wuhan Institute of Technology, Wuhan 430074, China;2. Key Laboratory of Green Chemical Process(Wuhan Institute of Technology), Ministry of Education, Wuhan 430074, China; 3. School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430074, China
关键词:
123-三唑稠杂环异喹啉衍生物合成开环反应
Keywords:
123-triazole fused heterocyclic isoquinoline derivative synthesis ring opening reaction
分类号:
O626.32+4
DOI:
10. 3969/j. issn. 1674?2869. 2016. 04. 003
文献标志码:
A
摘要:
以双炔基取代的苯类衍生物为原料,与叠氮化钠环合生成1,2,3-三唑稠杂环化合物,然后在110 ℃条件下经脱氮开环反应得到四个异喹啉类衍生物,并提出了可能的反应机理. 所有化合物经核磁共振氢谱和核磁共振碳谱表征以及高分辨质谱表征,波谱数据与化合物结构吻合. 实验结果表明,通过1,2,3-三唑稠杂环化合物在加热条件下的脱氮开环,可以得到了四个新型的异喹啉类衍生物,提供了一种间接的合成1,3-二取代的异喹啉类衍生物的方法,为异喹啉类衍生物的进一步研究奠定了基础.
Abstract:
The [1,2,3]triazole [5,1-а]-isoquinoline derivatives were synthesized by cycliaztion reaction with 1,2-bis(phenylethynyl) benzene derivatives and NaN3, then four isoquinoline derivatives were prepared by denitrogenation ring-opening reaction at the temperature of 110 ℃, and the reaction mechanism was also proposed in this paper. The structures of the compounds were confirmed by proton nuclear magnetic resonance spectroscopy and carbon-13 nuclear magnetic resonance spectroscopy and high-resolution mass spectrometry. Experimental results showed that through the denitrogenation ring-opening of 1,2,3-triazole under heating condition, four new isoquinoline derivatives were obtained easily, which provided a method for indirect synthesis of 1,4-disubstituted isoquinoline derivatives, and laid the foundations for further study .

参考文献/References:

[1] DABHOLHAR V V, TRIPATHI D R. Synthesis and antibacterial activity of isochromene and isoquinoline derivative [J]. Journal of heterocyclic chemistry, 2011, 48 (3) :529-532. [2] XU M, WAGERLE T, LONG J K, et al. Insecticidal quinoline and isoquinoline isoxazolines[J]. Bioorganic & medicinal chemistry letters, 2014, 24 (16): 4026-4030. [3] CZYRSKI A, HERMANN T, SMOLAG A. Optimization of a new isoquinoline derivative preparation [J]. Reaction kinetics mechanisms and catalysis, 2011, 104 (1) :173-180. [4] BROWN W D, GOULIAEV A H. Bromination of isoquinoline, quinoline, quinazoline and quinoxaline in strong acid [J]. Synthesis, 2002(1) :83-86. [5] HASSANEEN H M, WARDKHAN W W, MOHAMMED Y S. Synthesis and reactivity of 2-chloro-3-formylpyrido-[2,1-α]isoquinoline. A novel routes to pyrazolo[3’,4’:4,5]pyrido[2,1-α]isoquinoline and isoquinolino[2,1-g][1,6]naphthyridines[J]. Cheminform, 2013, 44 (16): 2933-2947. [6] MUCHOWSKI J M. 1-methylthio-3-lithioisoquinoline. The first simple isoquinoline derivative lithiated at the 3-position[J]. Arkivoc, 2005(6): 470-479. [7] 张健, 杨根生. 异喹啉衍生物的合成研究[J]. 浙江化工, 2008, 39(8):8-9. ZHANG J, YANG G S. Study on synthesis of isoquinoline derivatives[J]. Zhejiang chemical industry, 2008, 39(8):8-9. [8] CHEN Y F, ZHOU S L, MA S, et al. A facile synthesis of 5-amino-[1,2,3]triazolo[5,1-a]-isoquinoline derivatives through copper-catalyzed cascade reactions [J]. Organic and biomolecular chemistry, 2013, 11: 8171-8174. [9] TAO S P, HU Q Q, CHEN Y F, et al. Synthesis of [1,2,3]triazolo [5,1-a] isoquinoline derivatives via a selectively cascade cyclization sequence of 1,2-bis(phenylethynyl)benzene derivatives [J]. Synthetic communications, 2015, 45(11): 1354-1361. [10] 白银娟,路军,史真,等. 五元氮杂环的开环反应研究进展[J]. 有机化学. 2001, 9(21): 648-654. BAI Y J, LU J, SHI Z, et al. Recent development in ring-opening reaction of five-membered nitrogen- containing heterocycles[J]. Chinese journal of organic chemistry, 2001, 9(21):648-654.本文编辑:张 瑞

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备注/Memo

备注/Memo:
更新日期/Last Update: 2016-07-29