A Novel Synthesis of (E)-3-Methylthio-3-Substituted Arylamino-2-Cyanoacrylates under Microwave Irradiation
Abstract
:Introduction
Results and Discussion
Chemistry
Entry | Compd. No. | Substrate 2 | Solvent | Time/min | Temperature/°C | Yield/% |
---|---|---|---|---|---|---|
1 a | 3c | 4-trifluoromethylaniline | acetone | 30 | 50 | 33.7 |
2 a | 3c | 4-trifluoromethylaniline | THF | 30 | 50 | 31.2 |
3 a | 3c | 4-trifluoromethylaniline | DMF | 30 | 50 | 43.4 |
4 a | 3c | 4-trifluoromethylaniline | DMF+PhCH3 | 30 | 50 | 57.8 |
5 a | 3c | 4-trifluoromethylaniline | DMF+ THF | 30 | 50 | 64.0 |
6 a | 3c | 4-trifluoromethylaniline | DMF+ THF | 10 | 50 | 47.3 |
7 a | 3c | 4-trifluoromethylaniline | DMF+ THF | 20 | 50 | 51.3 |
8 a | 3c | 4-trifluoromethylaniline | DMF+ THF | 40 | 50 | 65.1 |
9 a | 3c | 4-trifluoromethylaniline | DMF+ THF | 30 | 25 | 45.5 |
10 a | 3c | 4-trifluoromethylaniline | DMF+ THF | 30 | 35 | 55.0 |
11 a | 3c | 4-trifluoromethylaniline | DMF+ THF | 30 | 45 | 53.0 |
12 a | 3c | 4-trifluoromethylaniline | DMF+ THF | 30 | 60 | 63.0 |
13 b | 3c | 4-trifluoromethylaniline | DMF+ THF | 600 | 50 | 43.0 |
Compound a | 3a | 3b | 3c | 3d | 3e | 3f | 3g |
---|---|---|---|---|---|---|---|
Ar- | |||||||
Yields /% b | 83.9 | 85.2 | 64.0 | 77.8 | 76.9 | 93.5 | 70.1 |
Yields /% c | 63.8 | 62.1 | 43.0 | 54.1 | 50.9 | 89.2 | 59.0 |
Biological activity
Compd. | PC3 cells | A431 cells |
---|---|---|
3a | 81.3±12.0 | 72.1±11.0 |
3b | 22.8±7.8 | 32.1±8.8 |
3c | 51.5±11.0 | 48.9±10.0 |
3d | 47.3±9.0 | 38.8±4.9 |
3e | 41.2±10.0 | 31.6±7.8 |
3f | 90.1±20.1 | 88.0±19.0 |
3g | 67.8±12.1 | 72.1±14.2 |
Conclusions
Experimental
General
General Method for the Preparation of (E)-3-Methylthio-3-Substituted Aryl Amino-2-Cyanoacrylates 3a-3g
MTT Cell Proliferation Assay
Acknowledgements
References
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- Samples Availability: Available from the author.
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Ouyang, G.; Song, B.; Zhang, H.; Yang, S.; Jin, L.; Li, Q.; Hu, D. A Novel Synthesis of (E)-3-Methylthio-3-Substituted Arylamino-2-Cyanoacrylates under Microwave Irradiation. Molecules 2005, 10, 1351-1357. https://doi.org/10.3390/10101351
Ouyang G, Song B, Zhang H, Yang S, Jin L, Li Q, Hu D. A Novel Synthesis of (E)-3-Methylthio-3-Substituted Arylamino-2-Cyanoacrylates under Microwave Irradiation. Molecules. 2005; 10(10):1351-1357. https://doi.org/10.3390/10101351
Chicago/Turabian StyleOuyang, Guiping, Baoan Song, Huiping Zhang, Song Yang, Linhong Jin, Qianzhu Li, and Deyu Hu. 2005. "A Novel Synthesis of (E)-3-Methylthio-3-Substituted Arylamino-2-Cyanoacrylates under Microwave Irradiation" Molecules 10, no. 10: 1351-1357. https://doi.org/10.3390/10101351