A simple and efficient synthesis of isocoumarins and alkylidenephthalides from 3-(1-hydroxycarbethoxy/alkyl)phthalides with a DEAD/PPh3/TBHP system
| Autor: | Sunita K. Gadakh, Arumugam Sudalai |
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| Rok vydání: | 2014 |
| Předmět: | |
| Zdroj: | RSC Adv.. 4:57658-57661 |
| ISSN: | 2046-2069 |
| DOI: | 10.1039/c4ra10372f |
| Popis: | A facile and novel approach to the synthesis of 3-carbethoxy-isocoumarins and 3-alkylidenephthalides is described. The methodology employs DEAD/PPh3/TBHP as the reagent system proceeding through unprecedented 1,2-shift intramolecular ring expansion or simple elimination depending upon substituents present on 3-substituted phthalides, with broader substrate scope. This strategy is amply demonstrated in the short synthesis of bioactive molecules such as cytogenin and (Z)-3-butylidene-7-hydroxy-5-methoxyphthalide. |
| Databáze: | OpenAIRE |
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