Abstract
A simple method for the synthesis of annulated 1,3-oxazolidin-2-ones from accessible ketones, acetylene, and carbon dioxide was developed. If their molecules contain arylalkyl substituents, intramolecular cyclization in acidic media gave rise to fused heterocyclic systems in high yields. The effects of the substituents in positions 3 and 5 of the oxazolidine ring on the regioselectivity of this cyclization were studied. The possibilities of converting oxazolidinones into cyclic cis-β-amino alcohols were studied.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 119–132, January, 2006.
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Chudinov, Y.B., Gashev, S.B., Chernysheva, N.B. et al. Synthesis of annulated oxazolidinones as potential precursors of cyclic cis-β-amino alcohols. Russ Chem Bull 55, 123–136 (2006). https://doi.org/10.1007/s11172-006-0225-z
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DOI: https://doi.org/10.1007/s11172-006-0225-z