Synthesis, reactions and stereochemistry of 3-hydroxymethyl-2,3-dihydro-4H-1,3-benzoxazin-4-one and some perhydrogenated derivatives☆

Add time:08/27/2019    Source:sciencedirect.com

3-Hydroxymethyl-2,3-dihydro-4H-1,3-benzoxazin-4-one and a number of its perhydrogenated derivatives were prepared from the corresponding 2-hydroxycarboxamides by treatment with a formaldehyde/formic acid mixture. Thermal decomposition of the 3-hydroxymethyl derivatives led to the previously unknown parent compounds. With one exception (14), both in the N-unsubstituted (16–18) and in the N-substituted (7–15) cyclopentane- and cyclohexane-fused derivatives the oxazinone ring predominantly attains a single half-chair conformation.

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