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Cyclization reaction of amines with dialkyl carbonates to yield 1,3-oxazinan-2-ones

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JournalPURE AND APPLIED CHEMISTRY
DateE-pub ahead of print - 23 Nov 2011
DatePublished (current) - Mar 2012
Issue number3
Volume84
Number of pages13
Pages (from-to)707-719
Early online date23/11/11
Original languageEnglish

Abstract

A number of six-membered cyclic carbamates (oxazinanones) were synthesized from the reaction of a primary amine or hydrazine with a dicarbonate derivative of 1,3-diols in a one-pot reaction, in good yield, short time span, and in the absence of a solvent. The reaction proceeds in two steps: an intermolecular reaction to give a linear intermediate and an intramolecular cyclization to yield the cyclic carbamate. This is the first example of a carbonate reacting selectively and sequentially, firstly at the carbonyl center to form a linear carbamate and then as a leaving group to yield a cyclic carbamate.

    Research areas

  • Cyclic carbamates, Cyclizations, Dialkyl carbonate, Green chemistry, Heterocyclic chemistry

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