Original TDAE Strategy Using Propargylic Chloride: Rapid Access to 1,4-Diarylbut-3-ynol Derivatives
Abstract
:1. Introduction
2. Results and Discussion
Entry a | Equiv. of 3a | Solvent | T1d | Time of reaction (stage 2) | T2e | (%) Yield c | ||
---|---|---|---|---|---|---|---|---|
1 | 4a | 5a | ||||||
1 | 3 | DMF, 4 mL | −20 °C | 2 h | rt | - | 40 | - |
2 b | 3 | THF, 4 mL | −20 °C | 2 h | rt | - | - | - |
3 | 3 | MeCN, 4 mL | −20 °C | 2 h | rt | 85 | - | - |
4 | 3 | DMF, 4 mL | −20 °C | 6 h | rt | - | 6 | traces |
5 | 1 | DMF, 4 mL | −20 °C | 2 h | rt | - | 12 | - |
6 | 4 | DMF, 4 mL | −20 °C | 2 h | rt | - | 20 | - |
7 | 3 | DMF, 10 mL | −20 °C | 2 h | rt | - | 38 | 20 |
8 | 3 | DMF, 4 mL | −50 °C | 2 h | rt | - | 45 | - |
9 | 3 | DMF, 4 mL | −50 °C | 2 h | 60 °C | - | 65 | - |
10 | 3 | DMF, 10 mL | −50 °C | 2 h | rt | - | 25 | 35 |
11 | 3 | DMF, 20 mL | −20 °C | 2 h | rt | - | 30 | traces |
12 | 3 | DMF, 20 mL | −50 °C | 2 h | rt | - | 38 | 25 |
13 | 3 | DMF, 20 mL | −50 °C | 6 h | rt | - | 25 | 25 |
Aromatic aldehyde | R | (%) Yield b | |
---|---|---|---|
4-Chlorobenzaldehyde | 4-Cl | 4a | 65 |
4-Nitrobenzaldehyde | 4-NO2 | 4b | 57 |
4-Fluorobenzaldehyde | 4-F | 4c | 34 c |
4-Tolualdehyde | 4-CH3 | 4d | traces |
4-Trifluoromethylbenzaldehyde | 4-CF3 | 4e | 51 |
2-Nitro-4,5-dimethoxybenzaldehyde | 2-NO2-4,5-(OCH3)2 | 4f | 32 |
Benzaldehyde | H | 4g | 30 d |
3. Experimental
3.1. General
3.2. General Procedure for TDAE Reaction with Aromatic Aldehydes
4. Conclusions
Acknowledgments
- Samples Availability: Samples of the compounds 4a–g, 5a are available from the authors.
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Roche, M.; Terme, T.; Vanelle, P. Original TDAE Strategy Using Propargylic Chloride: Rapid Access to 1,4-Diarylbut-3-ynol Derivatives. Molecules 2013, 18, 1540-1548. https://doi.org/10.3390/molecules18021540
Roche M, Terme T, Vanelle P. Original TDAE Strategy Using Propargylic Chloride: Rapid Access to 1,4-Diarylbut-3-ynol Derivatives. Molecules. 2013; 18(2):1540-1548. https://doi.org/10.3390/molecules18021540
Chicago/Turabian StyleRoche, Manon, Thierry Terme, and Patrice Vanelle. 2013. "Original TDAE Strategy Using Propargylic Chloride: Rapid Access to 1,4-Diarylbut-3-ynol Derivatives" Molecules 18, no. 2: 1540-1548. https://doi.org/10.3390/molecules18021540