High-yielding method for preparation of carbocyclic or N-containing heterocyclic [beta]-keto esters using in situ activated sodium hydride in dimethyl sulphoxide

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...

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Published in:Green chemistry letters and reviews 2016-03, Vol.9 (1), p.61
Main Authors: Popovic-Djordjevic, Jelena, Stepanovic, Stepan, Dosen-Micovic, Ljiljana, Ivanovic, Evica, Ivanovic, Milovan D
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Stepanovic, Stepan
Dosen-Micovic, Ljiljana
Ivanovic, Evica
Ivanovic, Milovan D
description 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 [beta]-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.
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title High-yielding method for preparation of carbocyclic or N-containing heterocyclic [beta]-keto esters using in situ activated sodium hydride in dimethyl sulphoxide
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