Experimental study demonstrates intramolecular cyclization of an isopulegol derivative into a bicyclic oxazepinone in 70% yield, highlighting concise access to chiral scaffolds.
The monoterpene-derived 1,4-oxazepan-3-one, (5aS,8R,9aR)-5,5,8-trimethyloctahydrobenzo[f][1,4]oxazepin-3(2H)-one, was synthesized from the corresponding (−)-isopulegol-based chloroacetamide by intramolecular cyclization in acetonitrile. The product was isolated in 70% yield as colorless crystals. Its structure was established by one- and two-dimensional NMR spectroscopy and high-resolution mass spectrometry and was confirmed by single-crystal X-ray diffraction analysis. The transformation provides concise access to a fused bicyclic 1,4-oxazepan-3-one bearing a stereochemically defined para-menthane scaffold.
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Ли-Жуланов et al. (2026) studied this question.
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