Efficient Solvent-Free Synthesis of Indolizines Using CuBr Catalyst from Pyridine, Acetophenone, and Electron-Deficient Alkenes
Abstract
:1. Introduction
2. Results and Discussions
3. Materials and Methods
3.1. Materials
3.2. Methods
3.2.1. Test Methods
3.2.2. Synthesis Methods
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Entry | Cat. | Oxidant (x Equiv) | T (°C) | t (h) | Yield [%] b |
---|---|---|---|---|---|
4a (4a’) | |||||
1 | CuBr | PIDA (2.0) | 110 | 12 | 34 (30) |
2 | CuCl | PIDA (2.0) | 110 | 12 | 26 (20) |
3 | Cu2O | PIDA (2.0) | 110 | 12 | 24 (22) |
4 | Cu2S | PIDA (2.0) | 110 | 12 | 24 (25) |
5 | CuBr | O2 | 110 | 12 | 36 (30) |
6 | CuBr | IBX (2.0) | 110 | 12 | 35 (31) |
7 | CuBr | (NH4)2S2O8 (2.0) | 110 | 12 | 65 (14) |
8 | CuBr | (NH4)2S2O8 (1.0) | 110 | 12 | 71 (15) |
9 | CuBr | (NH4)2S2O8 (3.0) | 110 | 12 | 63 |
10 | CuBr | (NH4)2S2O8 (4.0) | 110 | 12 | 56 |
11 | CuBr | (NH4)2S2O8 (1.0) | 120 | 12 | 72 |
12 | CuBr | (NH4)2S2O8 (1.0) | 130 | 12 | 76 |
13 | CuBr | (NH4)2S2O8 (1.0) | 140 | 12 | 73 |
14 | CuBr | (NH4)2S2O8 (1.0) | 130 | 10 | 75 |
15 | CuBr | (NH4)2S2O8 (1.0) | 130 | 8 | 76 |
16 | CuBr | (NH4)2S2O8 (1.0) | 130 | 6 | 78 |
17 | CuBr | (NH4)2S2O8 (1.0) | 130 | 5 | 80 (<5) |
18 | CuBr | (NH4)2S2O8 (1.0) | 130 | 4 | 78 |
19 c | CuBr | (NH4)2S2O8 (1.0) | 130 | 5 | 76 |
20 d | CuBr | (NH4)2S2O8 (1.0) | 130 | 5 | 55 |
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Zhang, X.; Zhang, J.; Liu, Z.; Bi, W.; Shen, J.; Li, G. Efficient Solvent-Free Synthesis of Indolizines Using CuBr Catalyst from Pyridine, Acetophenone, and Electron-Deficient Alkenes. Molecules 2024, 29, 2061. https://doi.org/10.3390/molecules29092061
Zhang X, Zhang J, Liu Z, Bi W, Shen J, Li G. Efficient Solvent-Free Synthesis of Indolizines Using CuBr Catalyst from Pyridine, Acetophenone, and Electron-Deficient Alkenes. Molecules. 2024; 29(9):2061. https://doi.org/10.3390/molecules29092061
Chicago/Turabian StyleZhang, Xueguo, Jianpeng Zhang, Zhengyi Liu, Wenxuan Bi, Jian Shen, and Guang Li. 2024. "Efficient Solvent-Free Synthesis of Indolizines Using CuBr Catalyst from Pyridine, Acetophenone, and Electron-Deficient Alkenes" Molecules 29, no. 9: 2061. https://doi.org/10.3390/molecules29092061