Heterogeneous Synergistic Catalysis for Promoting Aza-Michael–Henry Tandem Reaction for the Synthesis of Chiral 3-Nitro-1,2-Dihydroquinoline
Abstract
:1. Introduction
2. Results and Discussion
3. Experimental
3.1. Materials and Characterizations
3.2. Catalysts Preparation
3.3. Aza-Michael–Henry Cascade Reaction
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
References
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Entry | Catalyst | T (°C) | Solvent | Time (h) | Yield (%) a | EE (%) b |
---|---|---|---|---|---|---|
1 | SBA-15-Q | 35 | CH3OH | 48 | 19 | 86 |
2 | SBA-15-PY | 35 | CH3OH | 48 | 36 | 60 |
3 | SBA-15-AEP | 35 | CH3OH | 48 | 49 | 83 |
4 | SBA-15-AEP | 40 | CH3OH | 48 | 54 | 75 |
6 | SBA-15-AEP | 40 | i-PrOH | 48 | 70 | 99 |
7 | SBA-15-AEP | 40 | i-PrOH | 72 | 85 | 98 |
Entry | Catalyst | Yield (%) a | EE (%) b |
---|---|---|---|
1 | SBA-15-Q | 35 (39) | 99 (99) |
2 | Q | 50 | 10 |
3 | SBA-15-Q-CH3 | 10 | 70 |
4 | SBA-15-PY | 40 (41) | 71 (72) |
5 | PY | >99 | 15 |
6 | SBA-15-PY-CH3 | 20 | 65 |
7 | SBA-15-AEP | 85 (81) | 98 (98) |
8 | AEP | >99 | 8 |
9 | SBA-15-AEP-CH3 | 42 (45) | 40 (42) |
10 | SBA-15-SH | 3 | 14 |
11 | SBA-15-Br | 3 | 16 |
12 | - | 2 | 13 |
13 | SBA-15-P123-AEP | 39 | 25 |
Entry | R1 Group | R2 Group | Yield (%) a | EE (%) b |
---|---|---|---|---|
1 | H | 2,3-MeO-Ph | 67 (65) | 98 (98) |
2 | H | 4-Me-Ph | 60 (59) | 90 (93) |
3 | H | 2,4-Cl-Ph | 45 (40) | 97 (96) |
4 | H | 3,4-Cl-Ph | 42 (38) | 95 (97) |
5 | 3-MeO | Ph | 52 (50) | 95 (99) |
6 | 5-Cl | Ph | 55 (53) | 98 (99) |
7 | 3.5-Br | Ph | 68 (67) | 99 (98) |
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An, Z.; Chen, L.; Jiang, Y.; He, J. Heterogeneous Synergistic Catalysis for Promoting Aza-Michael–Henry Tandem Reaction for the Synthesis of Chiral 3-Nitro-1,2-Dihydroquinoline. Catalysts 2019, 9, 713. https://doi.org/10.3390/catal9090713
An Z, Chen L, Jiang Y, He J. Heterogeneous Synergistic Catalysis for Promoting Aza-Michael–Henry Tandem Reaction for the Synthesis of Chiral 3-Nitro-1,2-Dihydroquinoline. Catalysts. 2019; 9(9):713. https://doi.org/10.3390/catal9090713
Chicago/Turabian StyleAn, Zhe, Lifeng Chen, Yitao Jiang, and Jing He. 2019. "Heterogeneous Synergistic Catalysis for Promoting Aza-Michael–Henry Tandem Reaction for the Synthesis of Chiral 3-Nitro-1,2-Dihydroquinoline" Catalysts 9, no. 9: 713. https://doi.org/10.3390/catal9090713