High-yielding method for preparation of carbocyclic or N-containing heterocyclic β-keto esters using in situ activated sodium hydride in dimethyl sulphoxide
2016
Аутори
Popović-Djordjević, JelenaStepanović, Stepan
Došen-Mićović, Ljiljana
Ivanović, Evica R.
Ivanović, Milovan
Информативни прилог (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
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.
Кључне речи:
Acylation / condensation reaction / environmentally benign solventИзвор:
Green Chemistry Letters and Reviews, 2016, 9, 1, 61-68Финансирање / пројекти:
Напомена:
- Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3522
Колекције
Институција/група
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Popović-Djordjević, Jelena AU - Stepanović, Stepan AU - Došen-Mićović, Ljiljana AU - Ivanović, Evica R. AU - Ivanović, Milovan PY - 2016 UR - https://cherry.chem.bg.ac.rs/handle/123456789/115 AB - 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. T2 - Green Chemistry Letters and Reviews T1 - High-yielding method for preparation of carbocyclic or N-containing heterocyclic β-keto esters using in situ activated sodium hydride in dimethyl sulphoxide VL - 9 IS - 1 SP - 61 EP - 68 DO - 10.1080/17518253.2016.1145744 ER -
@article{ author = "Popović-Djordjević, Jelena and Stepanović, Stepan and Došen-Mićović, Ljiljana and Ivanović, Evica R. and Ivanović, Milovan", year = "2016", abstract = "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.", journal = "Green Chemistry Letters and Reviews", title = "High-yielding method for preparation of carbocyclic or N-containing heterocyclic β-keto esters using in situ activated sodium hydride in dimethyl sulphoxide", volume = "9", number = "1", pages = "61-68", doi = "10.1080/17518253.2016.1145744" }
Popović-Djordjević, J., Stepanović, S., Došen-Mićović, L., Ivanović, E. R.,& Ivanović, M.. (2016). High-yielding method for preparation of carbocyclic or N-containing heterocyclic β-keto esters using in situ activated sodium hydride in dimethyl sulphoxide. in Green Chemistry Letters and Reviews, 9(1), 61-68. https://doi.org/10.1080/17518253.2016.1145744
Popović-Djordjević J, Stepanović S, Došen-Mićović L, Ivanović ER, Ivanović M. High-yielding method for preparation of carbocyclic or N-containing heterocyclic β-keto esters using in situ activated sodium hydride in dimethyl sulphoxide. in Green Chemistry Letters and Reviews. 2016;9(1):61-68. doi:10.1080/17518253.2016.1145744 .
Popović-Djordjević, Jelena, Stepanović, Stepan, Došen-Mićović, Ljiljana, Ivanović, Evica R., Ivanović, Milovan, "High-yielding method for preparation of carbocyclic or N-containing heterocyclic β-keto esters using in situ activated sodium hydride in dimethyl sulphoxide" in Green Chemistry Letters and Reviews, 9, no. 1 (2016):61-68, https://doi.org/10.1080/17518253.2016.1145744 . .