Use of Phenacyl Thiosalicylates for the Preparation of 3-Hydroxybenzo[b]thiophene Derivatives
| Autor: | Pavel Hradil, Miroslav Soural, Patricia Trapani, Lubomir Kvapil |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
Reaction mechanism
010405 organic chemistry Organic Chemistry Reaction intermediate Nuclear magnetic resonance spectroscopy 010402 general chemistry Phenacyl 01 natural sciences Thiophene derivatives High-performance liquid chromatography 0104 chemical sciences chemistry.chemical_compound chemistry Organic chemistry |
| Zdroj: | Synlett. 29:810-814 |
| ISSN: | 1437-2096 0936-5214 |
| DOI: | 10.1055/s-0036-1591875 |
| Popis: | In this work, we attempted to synthesize thioflavonols using rearrangement of phenacyl thiosalicylates prepared by two different approaches and subjected to cyclization under acidic conditions. Contrary to our expectations, the isolated products were identified as (3-hydroxybenzo[b]thiophen-2-yl)(phenyl)methanones. The detailed reaction mechanism was elucidated by characterization of all reaction intermediates with HPLC and NMR spectroscopy. The applicability of the reaction using different phenacyl esters was tested. |
| Databáze: | OpenAIRE |
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