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Issue 3, 1998
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Synthesis of functionalised oxazoles and bis-oxazoles 1

Abstract

A new method for the synthesis of oxazoles, and in particular chiral non-racemic oxazoles derived from amino acids, has been developed. Thus, rhodium(II) catalysed reaction of diazocarbonyl compounds 6 and 11 in the presence of amides 8 and 10 results in regioselective insertion of the carbenoid into the amide N–H bond with formation of the β-carbonyl amides 9 and 12. Cyclodehydration of amides 9 and 12 using triphenylphosphine–iodine–triethylamine gives functionalised oxazoles 7 and 13. The oxazoles 13c and 13f were converted into the bis-oxazoles 17a and 17b by a second rhodium(II) catalysed regioselective N–H insertion reaction on the amides 15, followed by cyclodehydration.

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Article type: Paper
DOI: 10.1039/A704093H
Citation: J. Chem. Soc., Perkin Trans. 1, 1998,0, 591-600
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    Synthesis of functionalised oxazoles and bis-oxazoles 1

    M. C. Bagley, R. T. Buck, S. Lucy Hind and C. J. Moody, J. Chem. Soc., Perkin Trans. 1, 1998, 0, 591
    DOI: 10.1039/A704093H

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