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Microwave-Assisted Synthesis of 2-Aryl-2-oxazolines, 5,6-Dihydro-4H-1,3-oxazines, and 4,5,6,7-Tetrahydro-1,3-oxazepines

María C. Mollo and Liliana R. Orelli*

*Universidad de Buenos Aires, CONICET, Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica, Junín 956, 1113 Buenos Aires, Argentina, Email:

M. C. Mollo, L. R. Orelli, Org. Lett., 2016, 18, 6116-6119.

DOI: 10.1021/acs.orglett.6b03122 (free Supporting Information)

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Polyphosphoric acid (PPA) esters promote a microwave-assisted procedure for the synthesis of 5- to 7-membered cyclic iminoethers from amido alcohols. 2-Aryl-2-oxazolines and 5,6-dihydro-4H-1,3-oxazines were efficiently prepared using ethyl polyphosphate/CHCl3 in very good yields and short reaction time. Trimethylsilyl polyphosphate under solvent-free conditions enables the synthesis of 4,5,6,7-tetrahydro-1,3-oxazepines.

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Not of the Publisher:

Please check the following paper for more information about the 7-membered rings:

The Elusive Seven-Membered Cyclic Imino Ether Tetrahydrooxazepine
Bart Verbraeken, Jan Hullaert, Joachim van Guyse, Kristof Van Hecke, Johan Winne, Richard Hoogenboom


Preparation of PPE in CHCl3:

A mixture of P2O5 (150 g), dry chloroform (300 ml) and absolute ether (150 ml) were heated at 60-65ºC with stirring and protected from moisture until complete dissolution of the pentoxide (12-15 h). The solution was allowed to cool, filtered through glass wool and used.

Liliana R. Orelli, October 17, 2017

Key Words

oxazolines, microwave synthesis

ID: J54-Y2016