A New Valuable Synthesis of Polyfunctionalized Furans Starting from β-Nitroenones and Active Methylene Compounds
Abstract
:1. Introduction
2. Results and Discussion
3. Conclusions
4. Materials and Methods
4.1. General Section
4.2. Chemistry Section
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
Abbreviations
PS-carbonate | carbonate on polymer support (Sigma-Aldrich code: 21850: loading: 3.5 mmol/g) |
PS-DMAP | 4-(dimethylamino)pyridine, polymer-bound (Sigma-Aldrich code: 39410, loading: 3 mmol/g) |
PS-BEMP | 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine, polymer-bound (Sigma-Aldrich code: 20026, loading: 2.2 mmol/g) |
PS-TBD | 1,5,7-Triazabicyclo[4.4.0]dec-5-ene bound to polystyrene (Sigma-Aldrich code: 01961, loading: 3.0 mmol/g) |
PS-F | fluoride on polymer support (Sigma-Aldrich code: 47060, loading: 3.0 mmol/g) |
KF/alumina | potassium fluoride on aluminum oxide (Sigma-Aldrich code: 60244, loading: 5.5 mmol/g) |
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Sample Availability: Samples of the compounds 3a–n are available from the authors. |
Entry | Amberlyst 15 (g/mmol) | Solvent | Temperature (°C) 1 | Time (h) | Yield (%) of 3a 2 | E:Z |
---|---|---|---|---|---|---|
a | 1 | MeCN | 80 | 2 | 53 | 96:4 |
b | 1 | EtOAc | 80 | 2 | 76 | 96:4 |
c | 1 | Toluene | 80 | 2 | 68 | 82:18 |
d | 1 | 2-MeTHF | 80 | 2 | 58 | 90:10 |
e | 1 | EtOAc | 100 | 1 | 74 | 90:10 |
f | 1 | EtOAc | 60 | 4 | 45 | 96:4 |
g | 1.2 | EtOAc | 80 | 2 | 82 | 96:4 |
h | 0.8 | EtOAc | 80 | 2 | 89 | 96:4 |
i | 0.6 | EtOAc | 80 | 2 | 91 | 96:4 |
j | 0.4 | EtOAc | 80 | 2 | 85 | 96:4 |
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Chiurchiù, E.; Gabrielli, S.; Ballini, R.; Palmieri, A. A New Valuable Synthesis of Polyfunctionalized Furans Starting from β-Nitroenones and Active Methylene Compounds. Molecules 2019, 24, 4575. https://doi.org/10.3390/molecules24244575
Chiurchiù E, Gabrielli S, Ballini R, Palmieri A. A New Valuable Synthesis of Polyfunctionalized Furans Starting from β-Nitroenones and Active Methylene Compounds. Molecules. 2019; 24(24):4575. https://doi.org/10.3390/molecules24244575
Chicago/Turabian StyleChiurchiù, Elena, Serena Gabrielli, Roberto Ballini, and Alessandro Palmieri. 2019. "A New Valuable Synthesis of Polyfunctionalized Furans Starting from β-Nitroenones and Active Methylene Compounds" Molecules 24, no. 24: 4575. https://doi.org/10.3390/molecules24244575