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Paper | Regular issue | Vol 75, No. 6, 2008, pp.1385-1396
Published online, 26th February, 2008
DOI: 10.3987/COM-07-11313
A Facile Synthesis of Cycloether Systems Bearing [2,4]-Oxazole Units

Marcelo Incerti, Carolina Fontana, Laura Scarone, Guillermo Moyna, and Eduardo Manta*

*Cátedra de Química Farmacéutica, Departamento de Química Orgánica, Facultad de Química, Universidad de la República, Avenida General Flores 2124, Montevideo 11800, Uruguay

Abstract

We present a concise and high-yielding route for the preparation of novel five-, six-, and seven-membered cycloether systems bearing [2,4]-oxazoles units. The approach is based on intramolecular electrophilic oxirane ring expansion strategies and β-hydroxyamide cyclodehydration-oxidation reactions mediated by Deoxo-Fluor and BrCCl3/DBU.