Molecular sieve mediated sequential Knoevenagel condensation/decarboxylative Michael addition reaction: efficient and mild conditions for the synthesis of 3,3-disubstituted oxindoles with an all carbon quaternary center
| Autor: | Yi-Lin Guo, Ting-Shen Kuo, Hsuan-Hao Chang, Jeng-Liang Han, Yu-Hsun Li |
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| Rok vydání: | 2016 |
| Předmět: |
010405 organic chemistry
General Chemical Engineering chemistry.chemical_element General Chemistry Malonic acid 010402 general chemistry Molecular sieve 01 natural sciences 0104 chemical sciences chemistry.chemical_compound chemistry Michael reaction Organic chemistry Knoevenagel condensation Carbon Malononitrile |
| Zdroj: | RSC Advances. 6:74683-74690 |
| ISSN: | 2046-2069 |
| DOI: | 10.1039/c6ra16975a |
| Popis: | A one-pot, molecular sieve mediated sequential Knoevenagel condensation/decarboxylative Michael addition reaction has been developed. We discovered that the molecular sieves not only promoted the Knoevenagel condensation of isatins and malononitrile to generate isatylidene malononitriles, but also promoted the later decarboxylative Michael addition reactions of β-ketoacids and malonic acid half thioesters (MAHTs) with isatylidene malononitriles. This protocol provides a mild and efficient method for the preparation of 3,3-disubstituted oxindoles with an all carbon quaternary center in high yields. |
| Databáze: | OpenAIRE |
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