Citation: Xu Yang, Liao Lihao, Zhao Xiaodan. Progress in the Synthesis of Aza-Heterocyclic Compounds via Selenium-π-Acid Catalysis[J]. Chemistry, ;2020, 83(11): 970-976. shu

Progress in the Synthesis of Aza-Heterocyclic Compounds via Selenium-π-Acid Catalysis

Institute of Organic Chemistry & MOE Key Laboratory of Bioinorganic and Synthetic Chemistry, School of Chemistry, Sun Yat-Sen University, Guangzhou, 510275

Corresponding author: Zhao Xiaodan, zhaoxd3@mail.sysu.edu.cn
Received Date: 19 May 2020
Accepted Date: 5 July 2020

Figures(13)

The unique physiological and pharmacological activity of aza-heterocyclic compounds has aroused the interest of researchers. In recent years, many synthetic methods for the synthesis of aza-heterocyclic compounds have been reported. Among them, selenium-π-acid catalysis has attracted extensive attention due to mild reaction conditions, simple operation, and good regioselectivity and functional group compatibility. This short review convers the progress in the synthesis of aza-heterocyclic compounds such as indoles, pyrrolidines, dihydroquinolizidines, oxazoles, pyrazolo quinazolinones, isoquinolines, and 2-imidazolidone derivatives by selenium-π-acid catalysis.
- Aza-heterocyclic compounds,
- Selenium-π-acid catalysis,
- Synthetic methods
1. [1]
  Ferrari M D, Goadsby P J, Roon K I, et al. Cephalalgia, 2002, 22(8): 633~658.
2. [2]
  Shibano M, Tsukamoto D, Kusano G. Chem. Pharm. Bull., 1999, 47(6): 907~908.
3. [3]
  Weber W, Bacchus W, Daoud-El Baba M, et al. Nucleic Acids Res., 2007, 35(17): e116~e128.
4. [4]
  Bulawaa C E, Connelly S, DeVitc M, et al. PNAS, 2012, 109(24): 9629~9634.
5. [5]
  Michael J P. Nat. Prod. Rep., 2005, 22(5): 627~646.
6. [6]
  Cadia M D, Rienzo F D, Weston D A, et al. Bioorg. Med. Chem., 2013, 21(23): 7523~7528.
7. [7]
  Zhang H W, Ying C, Tang Y F. Chem. Biodivers., 2014, 11(1): 85~91.
8. [8]
  Neto J S S, Zeni G. Org. Chem. Front., 2020, 7(1): 155~210.
9. [9]
  Heravi M M, Nazari N. Curr. Org. Chem., 2017, 21(15): 1440~1529.
10. [10]
  Lukas V, Patrick W, Stefan M H. Angew. Chem. Int. Ed., 2019, 58(7), 1880~1891.
11. [11]
  He X, Wang X, Tse Y. Angew. Chem. Int. Ed., 2018, 57(39), 12869 ~12873.
12. [12]
  Ortgies S, Breder A. ACS Catal., 2017, 7(9): 5828~5840.
13. [13]
  Hori T, Sharpless K B. J. Org. Chem., 1979, 44(23): 4204~4208.
14. [14]
  Hori T, Sharpless K B. J. Org. Chem., 1979, 44(23): 4208~4210.
15. [15]
  Freudendahl D M, Santoro S, Shahzad S A, et al. Angew. Chem. Int. Ed., 2009, 48(45): 8409~8411.
16. [16]
  Freudendahl D M, Shahzad S A, Wirth T. Eur. J. Org. Chem., 2009(11), 1649~1664.
17. [17]
  Santi C, Santoro S, Battistelli B. Curr. Org. Chem., 2010, 14(20): 2442~2462.
18. [18]
  Guo R, Liao L, Zhao X. Molecules, 2017, 22(5): 835~837.
19. [19]
  Singh F V, Wirth T. Catal. Sci. Technol., 2019, 9(5): 1073~1091.
20. [20]
  Breder A, Depken C. Angew. Chem. Int. Ed., 2019, 58(1): 2~20.
21. [21]
  Rathore V, Jose C, Kumar S. New J. Chem., 2019, 43(23): 8852~8864.
22. [22]
  Shao L, Li Y, Lu J, et al. Org. Chem. Front., 2019, 6(16): 2999~3041.
23. [23]
  Ortgies S, Breder A. Org. Lett., 2015, 17(11): 2748~2751.
24. [24]
  Zhang X, Guo R, Zhao X. Org. Chem. Front., 2015, 2(10): 1334~1337.
25. [25]
  Guo R, Huang J, Huang H, et al. Org. Lett., 2016, 18(3): 504~507.
26. [26]
  Liao L, Guo R, Zhao X. Angew. Chem. Int. Ed., 2017, 56(12): 3201~3205.
27. [27]
  Horibe T, Ohmura S, Ishihara K. Org. Lett., 2017, 19(20): 5525~5528.
28. [28]
  Liao L, Zhang H, Zhao X. ACS Catal., 2018, 8(7): 6745~6750.
29. [29]
  Zhang Y, Shao Y, Gong J, et al. J. Org. Chem., 2019, 84(5): 2798~2807.
30. [30]
  Li H, Liao L, Zhao X. Synlett, 2019, 30(14): 1688~1692.
31. [31]
  Tao Z, Gilbert B B, Denmark S E. J. Am. Chem. Soc., 2019, 141(48): 19161~19170.
1. [1]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
2. [2]
  Feng Han , Fuxian Wan , Ying Li , Congcong Zhang , Yuanhong Zhang , Chengxia Miao . Comprehensive Organic Chemistry Experiment: Phosphotungstic Acid-Catalyzed Direct Conversion of Triphenylmethanol for the Synthesis of Oxime Ethers. University Chemistry, 2025, 40(3): 342-348. doi: 10.12461/PKU.DXHX202405181
3. [3]
  Fei Liu , Dong-Yang Zhao , Kai Sun , Ting-Ting Yu , Xin Wang . Comprehensive Experimental Design for Photochemical Synthesis, Analysis, and Characterization of Seleno-Containing Medium-Sized N-Heterocycles. University Chemistry, 2024, 39(3): 369-375. doi: 10.3866/PKU.DXHX202309047
4. [4]
  Geyang Song , Dong Xue , Gang Li . Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides. University Chemistry, 2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030
5. [5]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
6. [6]
  Lili Jiang , Shaoyu Zheng , Xuejiao Liu , Xiaomin Xie . Copper-Catalyzed Oxidative Coupling Reactions for the Synthesis of Aryl Sulfones: A Fundamental and Exploratory Experiment for Undergraduate Teaching. University Chemistry, 2025, 40(7): 267-276. doi: 10.12461/PKU.DXHX202408004
7. [7]
  Yan Kong , Wei Wei , Lekai Xu , Chen Chen . Electrochemical Synthesis of Organonitrogen Compounds from N-integrated CO₂ Reduction Reaction. Acta Physico-Chimica Sinica, 2024, 40(8): 2307049-0. doi: 10.3866/PKU.WHXB202307049
8. [8]
  Mengyang LI , Hao XU , Zhonghao NIU , Chunhua GONG , Weihui ZHONG , Jingli XIE . Highly effective catalytic synthesis of β-amino alcohols by using viologen-polyoxometalate hybrid materials. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1294-1300. doi: 10.11862/CJIC.20250080
9. [9]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
10. [10]
  Xilin Zhao , Xingyu Tu , Zongxuan Li , Rui Dong , Bo Jiang , Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106
11. [11]
  Zhen Yao , Bing Lin , Youping Tian , Tao Li , Wenhui Zhang , Xiongwei Liu , Wude Yang . Visible-Light-Mediated One-Pot Synthesis of Secondary Amines and Mechanistic Exploration. University Chemistry, 2024, 39(5): 201-208. doi: 10.3866/PKU.DXHX202311033
12. [12]
  Linjie ZHU , Xufeng LIU . Synthesis, characterization and electrocatalytic hydrogen evolution of two di-iron complexes containing a phosphine ligand with a pendant amine. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 939-947. doi: 10.11862/CJIC.20240416
13. [13]
  Yanan Liu , Yufei He , Dianqing Li . Preparation of Highly Dispersed LDHs-based Catalysts and Testing of Nitro Compound Reduction Performance: A Comprehensive Chemical Experiment for Research Transformation. University Chemistry, 2024, 39(8): 306-313. doi: 10.3866/PKU.DXHX202401081
14. [14]
  Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050
15. [15]
  Qianping Li , Hua Guan , Changfeng Wan , Yonghai Song , Jianwen Jiang . 大学有机化学复习课项目式教学——以“液晶化合物4-正戊基苯甲酸-4′-正戊基苯酯的合成路线设计与产品制备”为例. University Chemistry, 2025, 40(8): 100-116. doi: 10.12461/PKU.DXHX202410070
16. [16]
  Hong Lu , Yidie Zhai , Xingxing Cheng , Yujia Gao , Qing Wei , Hao Wei . Advancements and Expansions in the Proline-Catalyzed Asymmetric Aldol Reaction. University Chemistry, 2024, 39(5): 154-162. doi: 10.3866/PKU.DXHX202310074
17. [17]
  Aili Feng , Xin Lu , Peng Liu , Dongju Zhang . Computational Chemistry Study of Acid-Catalyzed Esterification Reactions between Carboxylic Acids and Alcohols. University Chemistry, 2025, 40(3): 92-99. doi: 10.12461/PKU.DXHX202405072
18. [18]
  Ying Liu , Jia Ji , Yinling Hou , Lilan Guo , Xuan Lv . Selenium’s Journey. University Chemistry, 2025, 40(7): 218-224. doi: 10.12461/PKU.DXHX202409046
19. [19]
  Hao Wu , Zhen Liu , Dachang Bai . ¹H NMR Spectrum of Amide Compounds. University Chemistry, 2024, 39(3): 231-238. doi: 10.3866/PKU.DXHX202309020
20. [20]
  Qianlang Wang , Jijun Sun , Qian Chen , Quanqin Zhao , Baojuan Xi . The Appeal of Organophosphorus Compounds: Clearing Their Name. University Chemistry, 2025, 40(4): 299-306. doi: 10.12461/PKU.DXHX202405205

Get Citation

PDF

XML

Metrics

PDF Downloads(22)
Abstract views(1383)
HTML views(352)

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