High-yielding method for preparation of carbocyclic or N-containing heterocyclic β-keto esters using in situ activated sodium hydride in dimethyl sulphoxide
| Autor: | Evica R. Ivanović, Jelena Popović-Djordjević, Stepan Stepanović, Ljiljana Dosen-Micovic, Milovan D. Ivanović |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2016 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry Chemistry Acylation General Chemistry 010402 general chemistry Condensation reaction 01 natural sciences Dieckmann condensation 0104 chemical sciences Sodium hydride Solvent condensation reaction lcsh:Chemistry chemistry.chemical_compound Deprotonation environmentally benign solvent lcsh:QD1-999 Alkoxide Environmental Chemistry Organic chemistry lcsh:Q lcsh:Science Alkyl |
| Zdroj: | Green Chemistry Letters and Reviews, Vol 9, Iss 1, Pp 61-68 (2016) Green Chemistry Letters and Reviews |
| ISSN: | 1751-7192 1751-8253 |
| Popis: | It was found that NaH suspension in DMSO was highly activated when reacted with an alcohol. The in situ generated NaH/alkoxide mixture permitted very rapid and complete deprotonation and acylation of various cyclic ketones with alkyl carbonates at ambient temperature. Activated NaH/alkoxide in DMSO is particularly effective in Dieckmann condensations, where it affords 5- and 6-membered carbocyclic or N-containing heterocyclic β-keto esters in high yields. A heterocyclic Dieckmann condensation was performed on a molar scale, demonstrating the scalability of the procedure. Besides, DMSO is non-toxic, relatively inexpensive and environmentally benign solvent. © 2016 The Author(s). Published by Taylor & Francis. Supplementary material: [http://cherry.chem.bg.ac.rs/handle/123456789/3522] |
| Databáze: | OpenAIRE |
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