Revisiting the Reaction Between Diaminomaleonitrile and Aromatic Aldehydes: a Green Chemistry Approach
Abstract
:Introduction
Results and Discussion
2a | 2b | 2c | 2d | 2e | 2f | 2g | 2h | 2i | 2j | 2k | |
---|---|---|---|---|---|---|---|---|---|---|---|
NH2 | 7.94 | 7.77 | 7.76 | 7.76 | 7.86 | 7.72 | 8,19 | 8.27 | 8.27 | 7.77 | 7.77 |
1 | 113.7 | 115.1 | 115.1 | 115.2 | 115.0 | 115.2 | 114.6 | 114.9 | 114.6 | 114.9 | 114.8 |
2 | 126.9 | 126.3 | 126.3 | 125.9 | 126.5 | 125.8 | 128.4 | 129.4 | 128.6 | 126.7 | 127.7 |
3 | 103.9 | 103.6 | 103.6 | 103.9 | 103,9 | 103.9 | 103.0 | 103.0 | 102.0 | 103.7 | 103.7. |
4 | 112.9 | 114.3 | 114.3 | 114.4 | 114.4 | 114.4 | 114.0 | 114.5 | 114.1 | 114.1 | 114.3 |
ArCHN | 156.1 | 155.2 | 155.2 | 155.6 | 153.4 | 155.8 | 150.4 | 150.9 | 153.2 | 143.5 | 153.6 |
8.31 | 8.21 | 8.20 | 8.16 | 8.59 | 8.13 | 8.56 | 8.61 | 8.39 | 8.08 | 8.85 | |
1´ | 135.7 | 128.9 | 128.7 | 127.4 | 121.7 | 127.8 | 133.3 | 130.2 | 137.7 | 151.9 | 134.8 |
2´ | 128.5 | 131.4 | 131.5 | 131.7 | 158.6 | 112.7 | 135.1 | 149.9 | 123.3 | --- | 134.8 |
7.93 | 7.98 | 7.97 | 7.87 | --- | 7.65 | --- | --- | 8.87 | --- | --- | |
3´ | 128.6 | 114.7 | 115.2 | 116.2 | 116.9 | 147.8 | 130.5 | 125.6 | 148.7 | 118.1 | 130.0 |
7.47 | 7.02 | 7.00 | 6.84 | 6.92 | --- | 7.55 | 8.08 | --- | 7.27 | 8.28 | |
4´ | 131.3 | 162.6 | 161.9 | 161.4 | 133.7 | 151.3 | 133.7 | 132.6 | 125.8 | 113.5 | 131.4 |
7.48 | 7.44 | --- | 6.97 | 7.33 | --- | 7.50 | 7.71 | 8.29 | 6.73 | 7.56 | |
5´ | 128.6 | 114.7 | 115.2 | 116.2 | 119.9 | 115.9 | 127.9 | 134.3 | 130.6 | 147.5 | 131.4 |
7.47 | 7.02 | 7.00 | 6.84 | 6.91 | 6.85 | 7.40 | 7.81 | 7.75 | 7.96 | 7.56 | |
6´ | 128.5 | 131.4 | 131.5 | 131.7 | 129.4 | 125.2 | 129.5 | 130.4 | 135.5 | --- | 130.0 |
7.93 | 7.98 | 7.97 | 7.87 | 8.03 | 7.35 | 8.44 | 8,53 | 8.44 | --- | 8.28 |
2a | 2b | 2d | 2e | 2f | 2g | 2h | 2i | 2j | 2k | |
---|---|---|---|---|---|---|---|---|---|---|
ArCHN | 8.31 | 8.21 | 8.16 | 8.59 | 8.13 | 8.56 | 8.61 | 8.39 | 8.08 | 8.85 |
2a | 2b | 2c | 2d | 2e | 2f | 2g | 2h | 2i | 2j | 2k | |
---|---|---|---|---|---|---|---|---|---|---|---|
CN1 | 2240 | 2231 | 2237 | 2247 | 2235 | 2231 | 2245 | 2247 | 2237 | 2237 | 2237 |
CN4 | 2205 | 2207 | 2197 | 2200 | 2206 | 2212 | 2203 | 2204 | 2200 | 2200 | 2200 |
Aldehyde | Product | Procedure A | Procedure B |
---|---|---|---|
Benzaldehyde | 2a | 78 | 49 |
p-Methoxybenzaldehyde | 2b | 93 | 62 |
3-Ethoxy-4-hydroxybenzaldehyde | 2f | 53 | 38 |
o-Chlorobenzaldehyde | 2g | 79 | 14 |
Conclusions
Experimental
General
General procedures for the synthesis of imines 2a-k
Acknowledgements
References
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Rivera, A.; Ríos-Motta, J.R.-M.; León, F. Revisiting the Reaction Between Diaminomaleonitrile and Aromatic Aldehydes: a Green Chemistry Approach. Molecules 2006, 11, 858-866. https://doi.org/10.3390/11110858
Rivera A, Ríos-Motta JR-M, León F. Revisiting the Reaction Between Diaminomaleonitrile and Aromatic Aldehydes: a Green Chemistry Approach. Molecules. 2006; 11(11):858-866. https://doi.org/10.3390/11110858
Chicago/Turabian StyleRivera, Augusto, Jaime Ríos-Motta Ríos-Motta, and Francisco León. 2006. "Revisiting the Reaction Between Diaminomaleonitrile and Aromatic Aldehydes: a Green Chemistry Approach" Molecules 11, no. 11: 858-866. https://doi.org/10.3390/11110858
APA StyleRivera, A., Ríos-Motta, J. R.-M., & León, F. (2006). Revisiting the Reaction Between Diaminomaleonitrile and Aromatic Aldehydes: a Green Chemistry Approach. Molecules, 11(11), 858-866. https://doi.org/10.3390/11110858