High-yielding method for preparation of carbocyclic or N-containing heterocyclic β-keto esters using in situ activated sodium hydride in dimethyl sulphoxide
2016
Authors
Popović-Djordjević, JelenaStepanović, S.
Došen-Mićović, Ljiljana I.
Ivanović, Evica
Ivanović, M.D.
Contribution To Periodical (Published version)
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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.
Keywords:
Acylation / condensation reaction / environmentally benign solventSource:
Green Chemistry Letters and Reviews, 2016, 9, 1, 61-68Publisher:
- Taylor and Francis Ltd.
Funding / projects:
- Structure-activity relationship of newly synthesized biological active compound (RS-MESTD-Basic Research (BR or ON)-172032)
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Poljoprivredni fakultetTY - 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 . .