High-yielding method for preparation of carbocyclic or N-containing heterocyclic β-keto esters using in situ activated sodium hydride in dimethyl sulphoxide
| Autor: | Jelena Popović-Djordjević, Stepan Stepanović, Ljiljana Došen-Mićović, Evica Ivanović, Milovan D. Ivanović |
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| Jazyk: | angličtina |
| Rok vydání: | 2016 |
| Předmět: | |
| Zdroj: | Green Chemistry Letters and Reviews, Vol 9, Iss 1, Pp 61-68 (2016) |
| Druh dokumentu: | article |
| ISSN: | 1751-8253 1751-7192 17518253 |
| DOI: | 10.1080/17518253.2016.1145744 |
| 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. |
| Databáze: | Directory of Open Access Journals |
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