Recyclable Fe3O4 Nanoparticles Catalysts for Aza-Michael Addition of Acryl Amides by Magnetic Field
Abstract
:1. Introduction
2. Results and Discussion
3. Experimental
3.1. Synthesis of Magnetic Fe3O4nanoparticles
3.2. Characterization
3.3. Representative Procedure for Catalytic Reactions
- 3-morpholinopropanamide (Table 2, entry 1). 1H NMR (600 MHz, CDCl3) (ppm): δ 7.92 (s, 1H), 5.64 (s, 1H), 3.90–3.80 (m, 2H), 3.72 (s, 2H), 2.41–2.63 (m, 8H).
- 3-(pyrrolidin-1-yl)propanamide (Table 2, entry 2). 1H NMR (600 MHz, CDCl3) (ppm): δ 8.00 (s, 1H), 5.38 (s, 1H), 2.86 (t, J = 6.2 Hz, 2H), 2.70 (s, 4H), 2.52 (t, J = 6.2 Hz, 2H), 1.91–1.80 (m, 4H).
- 3-(2-methylpiperidin-1-yl)propanamide (Table 2, entry 3). 1H NMR (600 MHz, CDCl3) (ppm): δ 8.38 (s, 1H), 5.56 (s, 1H), 3.72 (q, J = 7.0 Hz, 2H), 3.40 (d, J = 11.9 Hz, 2H), 2.81 (t, J = 11.0 Hz, 2H), 1.89 (s, 1H), 1.67 (d, J = 12.7 Hz, 2H), 1.49 (d, J = 6.5 Hz, 2H), 1.3 (t, J = 7.0 Hz, 2H), 1.12 (d, J = 6.3 Hz, 3H).
- 3-(4-methylpiperidin-1-yl)propanamide (Table 2, entry 4). 1H NMR (600 MHz, CDCl3) (ppm): δ 8.47 (s, 1H), 5.48 (s, 1H), 3.73 (q, J = 7.0 Hz, 2H), 2.94 (d, J = 11.4 Hz, 2H), 2.62–2.56 (m, 2H), 2.40 (t, J = 6.0 Hz, 2H), 1.98 (t, J = 12.3 Hz, 2H), 1.68 (d, J = 13.4 Hz, 1H), 1.25 (t, J = 8.3 Hz, 2H), 0.94 (d, J = 6.5 Hz, 3H).
- 3-(4-ethylpiperazin-1-yl)propanamide (Table 2, entry 5). 1H NMR (600 MHz, CDCl3) (ppm): δ 8.09 (s, 1H), 5.47 (s, 1H), 2.68–2.60 (m, 3H), 2.47–2.37 (m, 11H), 1.10 (t, J = 7.2 Hz, 3H).
- 3-(benzylamino)propanamide (Table 2, entry 6). 1H NMR (600 MHz, CDCl3) (ppm): δ 7.49(s, 1H), 7.23–7.25 (m, 4H), 6.26 (s, 1H), 3.71 (s, 4H), 1.33 (d, J = 6.9 Hz, 2H), 1.23 (t, J = 6.7 Hz, 2H).
- 3-morpholino-1-morpholinopropan-1-one (Table 2, entry 7). 1H NMR (600 MHz, CDCl3) (ppm): δ 3.71 (t, J = 4.5 Hz, 4H), 3.68–3.60 (m, 2H), 3.60 (s, 4H), 3.45 (d, J = 4.7 Hz, 2H), 2.74 (t, J = 7.4 Hz, 2H), 2.52 (d, J = 19.6 Hz, 4H), 2.36 (s, 4H).
- 1-morpholino-3-(pyrrolidin-1-yl)propan-1-one (Table 2, entry 8). 1H NMR (600 MHz, CDCl3) (ppm): δ 3.71–3.60 (m, 6H), 3.57 (d, J = 4.7 Hz, 2H), 2.93 (t, J = 7.3 Hz, 6H), 2.04 (s, 4H).
- 3-(2-methylpiperidin-1-yl)-1-morpholinopropan-1-one (Table 2, entry 9). 1H NMR (600 MHz, CDCl3) (ppm): δ 3.70 (q, J = 7.0 Hz, 4H), 3.41 (d, J = 12.7 Hz, 4H), 2.79 (t, J = 11.1 Hz, 2H), 2.52 (d, J = 7.8 Hz, 2H), 2.41 (s, 2H), 1.85 (s, 1H), 1.68 (s, 1H), 1.46 (d, J = 9.8 Hz, 2H), 1.42 (t, J = 7.0 Hz, 2H), 1.06 (s, 3H).
- 3-(4-methylpiperidin-1-yl)-1-morpholinopropan-1-one (Table 2, entry 10). 1H NMR (600 MHz, CDCl3) (ppm): δ 3.76–3.67 (m, 1H), 3.67–3.58 (m, 4H), 3.53–3.45 (m, 5H), 2.93 (d, J = 11.5 Hz, 2H), 2.79–2.71 (m, 2H), 2.63–2.55 (m, 2H), 2.06 (t, J = 11.0 Hz, 2H), 1.96 (s, 1H), 1.65 (d, J = 13.5 Hz, 2H), 0.93 (d, J = 6.5 Hz, 3H).
- 3-(4-ethylpiperazin-1-yl)-1-morpholinopropan-1-one (Table 2, entry 11). 1H NMR (600 MHz, CDCl3) (ppm): δ 3.69–3.68 (m, 6H), 3.49 (d, J = 5.0 Hz, 2H), 2.53 (d, J = 8.0 Hz, 2H), 2.45–2.29 (m, 12H), 1.11 (t, J = 7.2 Hz, 3H).
- 3-(benzylamino)-1-morpholinopropan-1-one (Table 2, entry 12). 1H NMR (600 MHz, CDCl3) (ppm): δ 7.49 (d, J = 6.2 Hz, 5H), 4.12 (s, 2H), 3.64 (d, J = 3.6 Hz, 4H), 3.54 (s, 4H), 2.97 (s, 2H), 2.03 (s, 2H), 1.24 (s, 1H).
- 3-morpholin-4-yl-N-phenyl-propionamide (Table 2, entry 13). 1H NMR (400 MHz, CDCl3) (ppm): δ 11.31 (s, 1H), 7.53 (d, J = 8.6 Hz, 2H), 7.30 (d, J = 9.9 Hz, 2H), 7.07 (t, J = 7.4 Hz, 1H), 3.04 (d, J = 11.7 Hz, 2H), 2.72–2.64 (m, 4H), 2.55–2.47 (m, 2H), 2.07 (t, J = 10.8 Hz, 4H).
- N-phenyl-3-pyrrolidin-1-yl-propionamide (Table 2, entry 14).1H NMR (600 MHz, CDCl3) (ppm): δ 9.97 (s, 1H), 7.66 (d, J = 7.9 Hz, 2H), 7.29 (d, J = 7.0 Hz, 2H), 7.09 (t, J = 7.3 Hz, 1H), 3.73 (q, J = 7.0 Hz, 2H), 3.11 (t, J = 6.5 Hz, 2H), 2.08 (s, 4H), 1.25 (t, J = 7.0 Hz, 4H).
- 3-(4-methyl-piperidin-1-yl)-N-phenyl-propionamide (Table 2, entry 15). 1H NMR (400 MHz, CDCl3) (ppm): δ 10.76 (s, 1H), 7.53 (d, J = 7.9 Hz, 2H), 7.32 (t, J = 7.8 Hz, 2H), 7.08 (t, J = 7.4 Hz, 1H), 3.82 (s, 2H), 2.87 (d, J = 23.3 Hz, 2H), 2.86 (d, J = 37.1 Hz, 2H), 2.71 (d, J = 29.6, 23.8 Hz, 2H), 1.74 (m, 1H), 1.25 (s, 4H), 0.86 (s, 3H).
- 3-benzylamino-N-phenyl-propionamide (Table 2, entry 16). 1H NMR (600 MHz, CDCl3) (ppm): δ 10.44 (s, 1H), 7.52 (d, J = 7.8 Hz, 2H), 7.41–7.25 (m, 7H), 7.07 (s, 1H), 3.88 (s, 2H), 2.97 (m, 2H), 2.59–2.51 (m, 2H), 1.94 (d, J = 6.7 Hz, 1H).
- 3-butyl-N-phenyl-propionamide (Table 2, entry 17). 1H NMR (600 MHz, CDCl3) (ppm): δ 10.51 (s, 1H), 7.45 (d, J = 7.9 Hz, 2H), 7.24 (m, 2H), 6.97 (t, J = 7.4 Hz, 1H), 2.95 (m, 2H), 2.57 (t, J = 7.0 Hz, 4H), 1.37 (d, J = 8.6 Hz, 4H), 1.23 (s, 1H), 0.78 (s, 3H).
- 3-propyl-N-phenyl-propionamide (Table 2, entry 18). 1H NMR (600 MHz, CDCl3) (ppm): δ9.44 (s, 1H), 7.51 (s, 2H), 7.25 (s, 2H), 7.02 (s, 1H), 2.95 (s, 2H), 2.55 (d, J = 1.2 Hz, 4H), 1.57 (s, 1H), 1.42 (s, 2H), 0.86 (t, J = 7.3 Hz, 3H).
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Entry | Acryl Amide | Amine | Catalyst | Yield (%) b |
---|---|---|---|---|
1 | - | 38.1 | ||
2 | Fe3O4 nanoparticles | 89.0 | ||
3 | - | 36.2 | ||
4 | Fe3O4 nanoparticles | 85.2 | ||
5 | - | 39.6 | ||
6 | Fe3O4 nanoparticles | 93.2 |
Entry | Acryl Amides | Amine | Product | Yield (%) b |
---|---|---|---|---|
1 | 89.0 | |||
2 | 90.6 | |||
3 | 90.4 | |||
4 | 91.7 | |||
5 | 90.1 | |||
6 | 80.2 | |||
7 | 85.2 | |||
8 | 86.9 | |||
9 | 84.3 | |||
10 | 85.6 | |||
11 | 80.2 | |||
12 | 90.1 | |||
13 | 93.2 | |||
14 | 81.2 | |||
15 | 84.6 | |||
16 | 80.1 | |||
17 | 78.6 | |||
18 | 77.9 |
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Li, Z.-X.; Luo, D.; Li, M.-M.; Xing, X.-F.; Ma, Z.-Z.; Xu, H. Recyclable Fe3O4 Nanoparticles Catalysts for Aza-Michael Addition of Acryl Amides by Magnetic Field. Catalysts 2017, 7, 219. https://doi.org/10.3390/catal7070219
Li Z-X, Luo D, Li M-M, Xing X-F, Ma Z-Z, Xu H. Recyclable Fe3O4 Nanoparticles Catalysts for Aza-Michael Addition of Acryl Amides by Magnetic Field. Catalysts. 2017; 7(7):219. https://doi.org/10.3390/catal7070219
Chicago/Turabian StyleLi, Zhen-Xing, Dan Luo, Ming-Ming Li, Xiao-Fei Xing, Zheng-Zheng Ma, and Hao Xu. 2017. "Recyclable Fe3O4 Nanoparticles Catalysts for Aza-Michael Addition of Acryl Amides by Magnetic Field" Catalysts 7, no. 7: 219. https://doi.org/10.3390/catal7070219