Synthesis and reactivity of alpha-sulfenyl-beta-chloroenones, including oxidation and Stille cross-coupling to form chalcone derivatives
| Autor: | Aoife M. Kearney, Simon E. Lawrence, Anita R. Maguire, Stuart G. Collins, Kevin S. Eccles, Chloe C. Murphy, Linda Murphy |
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| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
Chalcone
Substituent 010402 general chemistry 01 natural sciences Biochemistry Medicinal chemistry Transformation Tools chemistry.chemical_compound Stille cross-coupling Chalcones Drug Discovery Oxidation Chlorination Reactivity (chemistry) Alkyl chemistry.chemical_classification 010405 organic chemistry Organic Chemistry α-Sulfenyl-β-chloroenones 0104 chemical sciences Stille reaction Thioamides chemistry Stereoselectivity Isomerization |
| Popis: | The synthesis of a range of novel α-sulfenyl-β-chloroenones from the corresponding α-sulfenylketones, via a NCS mediated chlorination cascade, is described. The scope of the reaction has been investigated and compounds bearing alkyl- and arylthio substituents have been synthesised. In most instances, the Z α-sulfenyl-β-chloroenones were formed as the major products, while variation of the substituent at the β-carbon position led to an alteration in stereoselectivity. Stille cross-coupling with the Z α-sulfenyl-β-chloroenones led to selective formation of Z sulfenyl chalcones, while the E α-sulfenyl-β-chloroenones did not react under the same conditions. Oxidation of the Z α-sulfenyl-β-chloroenones was followed by isomerisation, leading to the E α-sulfinyl-β-chloroenones. Stille cross-coupling with the E α-sulfinyl-β-chloroenones produced the E sulfinyl chalcones. Either the E or Z sulfinyl chalcones can be obtained by altering the sequence of oxidation and Stille cross-coupling. |
| Databáze: | OpenAIRE |
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