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18.6.3.1.3.1.1 Variation 1: Reaction with 1,3,5-Triazinane-2,4,6-trione

DOI: 10.1055/sos-SD-018-00578

Rossi, L.Science of Synthesis, (200518573.

Oxazolidin-2-ones are prepared by the reaction of oxiranes with 1,3,5-triazinane-2,4,6-trione (cyanuric acid) (Scheme 158).[‌416‌‌418‌] With unsubstituted 1,3,5-triazinane-2,4,6-trione (224) it has been suggested that the acidic hydrogens bonded to the nitrogen atoms open the oxirane ring to form a triply substituted isocyanurate which, after pyrolytic collapse of the 1,3,5-triazinane-2,4,6-trione ring, furnishes 3 moles of oxazolidin-2-one 225. When substituted 1,3,5-triazinane-2,4,6-triones, e.g. 226, are used, a different mechanism must apply.

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