Reductive Amination Reaction Using Hantzsch Ester 1,4-Dihydropyridine as Reducing Reagent

doi:10.6023/cjoc201302016

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (9): 1960-1964.DOI: 10.6023/cjoc201302016 Previous Articles Next Articles

Articles

以汉斯酯1,4-二氢吡啶为还原剂的还原胺化反应研究

黄新炜^a,b, 刘建利^a

a 西北大学生命科学学院西部资源生物与现代生物技术省部共建教育部重点实验室西安 710069;
b 西安文理学院化学与化学工程学院西安 710065

收稿日期:2013-03-02 修回日期:2013-04-26 发布日期:2013-05-24
通讯作者: 刘建利 E-mail:jlliu@nwu.edu.cn
基金资助:
国家自然科学基金(Nos. 20872118, 30070905);陕西省重点实验室基金(Nos. 2010JS097, 11JS090, 12JS110);陕西省教育厅基金(No. 08jk477)资助项目

Reductive Amination Reaction Using Hantzsch Ester 1,4-Dihydropyridine as Reducing Reagent

Huang Xinwei^a,b, Liu Jianli^a

a Key Laboratory of Resource Biology and Biotechnology in Western China, Ministry of Education, School of Life Science, Northwest University, Xi'an 710069;
b School of Chemistry and Chemical Engineering, Xi'an University of Arts and Science, Xi'an 710065

Received:2013-03-02 Revised:2013-04-26 Published:2013-05-24
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 20872118, 30070905), the Key Laboratory Fund of Shaanxi Province of China (Nos. 2010JS097, 11JS090, 12JS110) and the Foundation of the Education Department of Shaanxi Province (No. 08jk477)

Reductive amination is an important reaction in organic synthesis. Aldehyde and ketone can react with primary and secondary amine in the presence of appropriate reducing reagent to afford secondary and tertiary amine. Hantzsch ester 1,4-dihydropyridine (HEH) is employed in the selective reduction and reductive amination of α,β-unsaturated carbonyl compounds, electron-deficient conjugate alkene and imine as a biomimetic organic reductant. In this paper, the possibility of labeling aldehyde by reductive amination using HEH as reductant, 7-amino-4-methylcoumarin and aldehydes as models was studied. Sixteen products were synthesized, among them, thirteen compounds were not reported in the literature.

Key words: Hantzsch ester 1,4-dihydropyridine, reductive amination, coumarin, aldehyde, label

Cite this article

Huang Xinwei, Liu Jianli. Reductive Amination Reaction Using Hantzsch Ester 1,4-Dihydropyridine as Reducing Reagent[J]. Chin. J. Org. Chem., 2013, 33(9): 1960-1964.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Huang, S.-W.; Peng, W.-L.; Shan, Z.-X.; Zhao, D.-J. Chem. Reag. 2000, 22, 65 (in Chinese).
(黄世文, 彭伟立, 单自兴, 赵德杰, 化学试剂, 2002, 22, 65).
[2] Fu, B.; Li, N.; Liang, X.-M.; Dong, Y.-H.; Wang, D.-Q. Chin. J. Org. Chem. 2007, 27, 1 (in Chinese).
(傅滨, 李楠, 梁晓梅, 董燕红, 王道全, 有机化学, 2007, 27, 1.)
[3] Wan, S.-S. China Pract. Med. 2010, 5, 223 (in Chinese).
(万斯斯, 中国实用医药, 2010, 5, 223).
[4] Yang, J. W.; Hechavarria Fonseca, M. T.; List, B. Angew. Chem., Int. Ed. 2004, 43, 6660.
[5] Liu, Q.; Li, J.; Shen, X.-X.; Xing, R.-G.; Yang, J.; Liu, Z.-G.; Zhou, B. Tetrahedron Lett. 2009, 50, 1026.
[6] Liu, Z.-G.; Liu, Q.; Zhang, W.; Mu, R.-Z.; Yang, L.; Liu, Z.-L.; Yu, W. Synthesis 2006, 771.
[7] Liu, Z.-G; Niu, X.-Q.; Yu, W.; Yang, L.; Liu, Z.-L. Chin. Chem. Lett. 2008, 19, 885.
[8] Niu, X.-Q.; Liu, Z.-G.; Yu, W.; Wu, L.-M. Chin. J. Org. Chem. 2009, 29, 229 (in Chinese).
(牛秀琴, 刘振刚, 于炜, 吴隆民, 有机化学, 2009, 29, 229.)
[9] Garden, S. J.; Guimaraes, C. R. W.; Correa, M. B.; de Oliveira C. A. F.; Pinto, A. D. C.; Alencastro, R. B. D. J. Org. Chem. 2003, 68, 8815.
[10] Nguyen, Q. P. B.; Kim, J. N.; Kim, T. H. Tetrahedron 2012, 68, 6513.
[11] Itoh, T.; Nagata, K.; Miyazaki, M.; Ishikawa, H.; Kurihara, A.; Ohsawa, A. Tetrahedron 2004, 60, 6649
[12] Itoh, T.; Nagata, K.; Kurihara, A.; Miyazaki, M.; Ohsawa, A. Tetrahedron Lett. 2002, 43, 3105.
[13] Nguyen, Q. P. B.; Kim, T. H. Tetrahedron Lett. 2011, 52, 5004.
[14] Liu, Z.-L.; Wang, C.-L.; Ling, Y.-P.; Wang, Y.-Y.; Liu, J.-L. Chemistry 2008, 9, 718 (in Chinese).
(刘竹兰, 王翠玲, 令亚萍, 王玉英, 刘建利, 化学通报, 2008, 9, 718.)
[15] Yang, J.-H.; Ji, C.-B.; Zhao, Y.-M. Chin. J. Org. Chem. 2008, 28, 1740 (in Chinese).
(杨金会, 计从斌, 赵艳敏, 有机化学, 2008, 28, 1740.)
[16] Ronad, P.; Dharbamalla, S.; Hunshal, R.; Maddi, V. Arch. Pharm. 2008, 341, 696.
[17] Creaven, B. S.; Czeglédi, E.; Devereux, M.; Enyedy, E. A.; Kia, A. F.; Karcz, D.; Kellett, A.; McClean, S.; Nagy, N. V.; Noble, A.; Rockenbauer, A.; Szabo-Plánka, T.; Walsh, M. Dalton Trans. 2010, 39, 10854.

以汉斯酯1,4-二氢吡啶为还原剂的还原胺化反应研究

Reductive Amination Reaction Using Hantzsch Ester 1,4-Dihydropyridine as Reducing Reagent

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Ruixia Cao, Yuping Jia. Synthesis and Biological Activity of Novel Pyrrolo[2,3-d]pyrimidine Derivatives Containing Coumarin [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3304-3311.
[2]	Wenqian Wu, Chunxia Chen, Jinsong Peng, Zhanyu Li. Research Progress of Carbonyl α-Position Amination [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2743-2763.
[3]	Xuzheng Zhang, Fengli Yu, Bing Yuan, Congxia Xie, Shitao Yu. Phase Transfer Catalytic Oxidation of Cyclopentene to Glutaraldehyde by Vanadium Molybdenum Heteropolyacid Salts [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1444-1451.
[4]	Yuliang Chen, Fengkai He, Siyun Wang, Dingcheng Jia, Yaqun Liu, Yiyong Huang. Kinetic Resolution of Aldehydes Bearing an All-Carbon Quaternary Stereocenter at the α-Position by the Antilla Allylboration [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4294-4302.
[5]	Jiling Yi, Kangqi Shi, Binglin Wu, Wanshan Li, Guangying Chen. Study on Secondary Metabolites of Marine-Derived Fungus Eutypella sp. F0219 [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 295-298.
[6]	Dongying Li, Shanguang Qiu, Yuxue Chen, Yanmei Zhao, Yunlong Wei, Luyong Wu, Wenhao Chen. Research for the Reaction of Base-Catalyzed Selective Hydrogen- Deuterium Exchange in Mono-1-substituted 1,2,3-Triazoles [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2898-2905.
[7]	Zengjin Dai, Xumu Zhang, Qin Yin. Advances on Asymmetric Reductive Amination with Ammonium Salts as Amine Sources [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2261-2274.
[8]	Fasheng Shi, Shengwen Wang, Huan Xu, Xingxing Lu, Xinling Yang, Tengda Sun, Changkai Wang, Xiaoming Zhang, Qing Yang, Yun Ling. Design, Synthesis and Fungicidal Actiνity of Noνel Thiosemicarbazide Compounds [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2106-2116.
[9]	Na Li, Xiaofeng Tan, Qinglai Yang. Recent Progress on Strategies and Applications of Imaging for Intestinal Microflora [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1375-1386.
[10]	Huixu Lu, Yonghe Tang, Hongmei Zhou, Weiying Lin. Synthesis and Study of Performance for An Enhanced Formaldehyde Fluorescent Probe [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1163-1169.
[11]	Mianyuan Wu, Yanchao Yu, Yang Liu, Jun You, Wenju Wu, Bo Liu. Synthesis and Application of a Novel Fluorescent Probe for Sequential Recognition Cu²⁺ and Glyphosate [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 803-811.
[12]	Yamin Sun, Xiyong Li, Jinwei Yuan, Jialin Yu, Shuainan Liu. CuI-Catalyzed Regioselective Synthesis of 3-Arylcoumarins with Arylamines under Mild Conditions [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 631-640.
[13]	Mingzhou Shang, Lanlan Zhang, Miaomiao Chen, Wangcheng Hu, Xinwei He, Hongjian Lu. Synthesis of Esterified/Fused Isocoumarins via Rh-Catalyzed C—H Activation/Transannulative Coupling/Annulation of Phthalic Anhydrides with Cyclic 2-Diazo-1,3-diketones and Methanol [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3816-3823.
[14]	Haorui Wang, Mengchun Ye. Research Advance on Enantioselective Transition Metal-Catalyzed Hydroacylation Reactions [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3152-3166.
[15]	Xiaoyu Yang, Jianlin Liu, Fangzhi Hu, Hongmei Sun, Liang Wang, Shuai-Shuai Li. Diverse Application of 4-Hydroxycoumarin in the Syntheses of Tetrahydroquinoline and Zwitterionic Biscoumarin Derivatives [J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2788-2799.