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Issue 4, 2009
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The use of phosphonium anhydrides for the synthesis of 2-oxazolines, 2-thiazolines and 2-dihydrooxazine under mild conditions

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Abstract

β-Hydroxy amides6 and 7 were treated with triphenylphosphonium anhydride trifluoromethane sulfonate (3), or the cyclic analogue 4, to generate 2-oxazolines 5 and 8 under mild conditions. The reaction was optimised by examining the number of equivalents of reagents 3 or 4, or diisopropylethyl amine required to best effect cyclisation. The effects of altering the reaction temperature, reaction time, concentration, solvent, and addition rate also were investigated. However, it was found that use of a trityl group to block reaction at the hydroxyl or thiol group of the starting amides, and subsequent in situ detritylation, in the absence of base, led to greatly improved yields. Reagent 4 offered significant advantages in the purification of products and was used to dehydrate a range of trityl derivatives to form simple oxazolines, thiazolines, and a dihydro-1,3-oxazine, in high yield (85–99%), as well as a tetrahydro-1,3-oxazepine (31%).

Graphical abstract: The use of phosphonium anhydrides for the synthesis of 2-oxazolines, 2-thiazolines and 2-dihydrooxazine under mild conditions

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Publication details

The article was received on 16 Oct 2008, accepted on 12 Nov 2008 and first published on 18 Dec 2008


Article type: Paper
DOI: 10.1039/B818310D
Citation: Org. Biomol. Chem., 2009,7, 739-746

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    The use of phosphonium anhydrides for the synthesis of 2-oxazolines, 2-thiazolines and 2-dihydrooxazine under mild conditions

    M. J. Petersson, I. D. Jenkins and W. A. Loughlin, Org. Biomol. Chem., 2009, 7, 739
    DOI: 10.1039/B818310D

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