Ugi四组分一锅法高效合成结构独特的活性生物碱化合物

引用本文: 李厚金, 许阳, 钟云竹, 章笑研, 朱芳, 陈六平. Ugi四组分一锅法高效合成结构独特的活性生物碱化合物[J]. 大学化学, 2020, 35(4): 178-186. doi: 10.3866/PKU.DXHX201910060 shu

Citation: Houjin Li, Yang Xu, Yunzhu Zhong, Xiaoyan Zhang, Fang Zhu, Liuping Chen. Synthesis of Unique Bioactive Alkaloids by Ugi Four-Component One-Pot Reaction[J]. University Chemistry, 2020, 35(4): 178-186. doi: 10.3866/PKU.DXHX201910060 shu

Ugi四组分一锅法高效合成结构独特的活性生物碱化合物

中山大学化学学院, 广州 510275
基金项目:
广东省高等教育教学改革项目；中山大学本科教学改革研究项目

摘要: 以α-氨基酸、醛、异腈和醇为原料，四组分在室温条件下通过一锅法反应制备得到结构独特的天然活性生物碱1，1’-亚胺基二羧酸衍生物。利用薄层色谱、高效液相色谱-质谱联用仪对反应进程进行监测，用硅胶柱层析对产物进行纯化，化合物的结构通过质谱、核磁共振波谱的解析确定。该反应是Ugi反应的创新发展，具有反应操作简单、产率高、立体选择性好、高原子经济性等特点，在新药设计与合成、组合化学和天然产物合成中具有广泛的应用。

关键词:

English

Synthesis of Unique Bioactive Alkaloids by Ugi Four-Component One-Pot Reaction

School of Chemistry, Sun Yat-Sen University, Guangzhou 510275, P. R. China
Received Date: 29 October 2019

Abstract: Using α-amino acids, aldehydes, isocyanides and alcohols as the starting materials, four components react in one pot at room temperature to obtain naturally unique bioactive alkaloids, 1,1'-iminodicarboxylic acid derivatives. The reaction process is monitored by thin layer chromatography and liquid chromatography-mass spectrometry, and the products are purified by silica gel column chromatography. The structures are determined by mass spectrometry and nuclear magnetic resonance spectroscopy. The reaction is an innovative development of Ugi reaction, which has the characteristics of simple reaction operation, high yield, good stereoselectivity and high atomic economy. It has been widely used in the design and synthesis of new drugs, combinatorial chemistry and natural product synthesis.

Key words:

Ugi reaction
/ Multi-component reaction
/ 1,1'-iminodicarboxylic acid derivatives
/ Alkaloid
/ One-pot reaction

1. [1] Li, J. J. Name Reactions:A Collection of Detailed Mechanisms and Synthetic Applications, 5th ed.; Springer International Publishing:Switzerland, 2014.
2. [2] Ruijter, E.; Orru, R. V. A. Drug Discov. Today:Technologies 2013, 10(1), e15.
3. [3] Hulme, C.; Gore, V. Curr. Med. Chem. 2003, 10(1), 51.
4. [4] Doemling, A.; Ugi, I. Angew. Chem. Int. Edit. 1993, 32 (4), 563.
5. [5] Flanagan, D. M.; Joullie, M. M. Synthetic Commun. 1989, 19 (1-2), 1.
6. [6] Bauer, S. M.; Armstrong, R. W. J. Am. Chem. Soc. 1999, 121 (27), 6355.
7. [7] Suda, A.; Ohta, A.; Sudoh, M.; Tsukuda, T.; Shimma, N. Heterocycles 2001, 55 (6), 1023.
8. [8] Tanino, T.; Ichikawa, S.; Shiro, M.; Matsuda, A. J. Org. Chem. 2010, 75 (5), 1366.
9. [9] Sharma, U. K.; Sharma, N.; Vachhani, D. D.; Van der Eycken, E. V. Chem. Soc. Rev. 2015, 44 (7), 1836.
10. [10] Riva, R. Science 2018, 361 (6407), 1072.
11. [11] Ugi, I.; Demharter, A.; Hörl, W.; Sehmid, T. Tetrahedron 1996, 52 (35), 11657.

扫一扫看文章

计量

PDF下载量: 10
文章访问数: 425
HTML全文浏览量: 32

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Ugi四组分一锅法高效合成结构独特的活性生物碱化合物

English

Synthesis of Unique Bioactive Alkaloids by Ugi Four-Component One-Pot Reaction

计量

文章相关

通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处