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Publicly Available Published by De Gruyter November 23, 2011

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

C. Robert McElroy, Fabio Aricò, Franco Benetollo and Pietro Tundo

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.

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Online erschienen: 2011-11-23
Erschienen im Druck: 2011-11-23

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