Stepanović, S.

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  • Stepanović, S. (1)
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High-yielding method for preparation of carbocyclic or N-containing heterocyclic β-keto esters using in situ activated sodium hydride in dimethyl sulphoxide

Popović-Djordjević, Jelena; Stepanović, S.; Došen-Mićović, Ljiljana I.; Ivanović, Evica; Ivanović, M.D.

(Taylor and Francis Ltd., 2016)

TY  - JOUR
AU  - Popović-Djordjević, Jelena
AU  - Stepanović, S.
AU  - Došen-Mićović, Ljiljana I.
AU  - Ivanović, Evica
AU  - Ivanović, M.D.
PY  - 2016
UR  - http://aspace.agrif.bg.ac.rs/handle/123456789/4167
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.
PB  - Taylor and Francis Ltd.
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
EP  - 68
IS  - 1
SP  - 61
VL  - 9
DO  - 10.1080/17518253.2016.1145744
ER  - 
@article{
author = "Popović-Djordjević, Jelena and Stepanović, S. and Došen-Mićović, Ljiljana I. and Ivanović, Evica and Ivanović, M.D.",
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.",
publisher = "Taylor and Francis Ltd.",
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",
pages = "68-61",
number = "1",
volume = "9",
doi = "10.1080/17518253.2016.1145744"
}
Popović-Djordjević, J., Stepanović, S., Došen-Mićović, L. I., Ivanović, E.,& Ivanović, M.D.. (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
Taylor and Francis Ltd.., 9(1), 61-68.
https://doi.org/10.1080/17518253.2016.1145744
Popović-Djordjević J, Stepanović S, Došen-Mićović LI, Ivanović E, 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, S., Došen-Mićović, Ljiljana I., Ivanović, Evica, Ivanović, M.D., "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 . .
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