Preparation of 2-(3-Methyleneindolin-2-yl)phenols via Sodium Hydride Promoted C–C/C–O Bond Cleavage
| Autor: | Xiuqiang Lu, Dong-Liang Mo, Feng-Ping Liu, Hong-Ping Zhao, Shuang Tan |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry Organic Chemistry 010402 general chemistry 01 natural sciences Medicinal chemistry Aldehyde Catalysis 0104 chemical sciences Sodium hydride chemistry.chemical_compound Cascade reaction Nucleophile chemistry Indoline Phenol Phenols Bond cleavage |
| Zdroj: | Synthesis. 51:3477-3484 |
| ISSN: | 1437-210X 0039-7881 |
| DOI: | 10.1055/s-0037-1611850 |
| Popis: | A variety of 2-(3-methyleneindolin-2-yl)phenols were prepared in good to excellent yields through a NaH-promoted C–C/C–O bond cleavage of fused indolines under mild and simple conditions. Mechanistic studies showed that NaH serves as a nucleophile, attacking the aldehyde group of indoline, which is followed by tandem C–C/C–O bond cleavage to afford the desired products. A representative 2-(3-methyleneindolin-2-yl)phenol was easily prepared on a gram scale. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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