Tandem grinding reactions involving aldol condensation and Michael addition in sequence for synthesis of 3,4,5-trisubstituted isoxazoles
| Autor: | Yue-Dan Li, Xiao-Mu Hu, Hai Dong, Zhuang Tian, Ping Huang, Ping-An Wang |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
chemistry.chemical_classification
Tandem General Chemical Engineering 02 engineering and technology General Chemistry 010402 general chemistry 021001 nanoscience & nanotechnology 01 natural sciences Pyrrolidine 0104 chemical sciences Grinding chemistry.chemical_compound chemistry Aldol reaction Michael reaction Organic chemistry Aldol condensation Methylene 0210 nano-technology Alkyl |
| Zdroj: | RSC Advances. 9:27883-27887 |
| ISSN: | 2046-2069 |
| DOI: | 10.1039/c9ra04864b |
| Popis: | A one-pot, base-catalyzed, tandem grinding process involving carrying out aldol condensation and Michael addition in sequence to produce 3,4,5-trisubstituted isoxazoles from 3,5-dimethyl-4-nitroisoxazole, aromatic aldehydes and activated methylene compounds has been developed. In the presence of 10 mol% of pyrrolidine, aldol condensations of 3,5-dimethyl-4-nitroisoxazole with various aromatic aldehydes were performed with 3–10 minutes of grinding to provide 5-styryl-3-methyl-4-nitroisoxazoles in good to quantitative yields without further purification. Then, Michael additions between 5-styryl-3-methyl-4-nitroisoxazoles and activated methylene compounds (including ethyl 2-nitroacetate and alkyl 2-cyanoacetates) were carried out in the presence of 10 mol% of Et3N in the same mortar with 3–5 minutes of continuous grinding to produce 3,4,5-trisubstituted isoxazoles in good to excellent yields. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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