The first two chapters are review articles. Chapter 1 by C. Access can be gained from the following locations:. Oxazoles, which have been known for well over a hundred years, have been of considerable interest to organic chemists ever since the 's, when the intense research effort on penicillin led Cornforth and others to develop new routes to the oxazole ring.
This work, summarised in the classic treatise in , is the foundation of modern oxazole chemistry. The subsequent discovery during the 's by Kondrat'eva that oxazoles can function as azadienes in the Diels-Alder reaction, and by Huisgen that mesoionic oxazoles participate in 1,3-dipolar cycloaddition reactions prompted further research into the ring system. More recently the oxazole ring system has been found in an ever increasing range of natural products, many of them "peptide alkaloids" in which the heterocyclic ring is most likely formed by a modification of a serine or threonine containing peptide.
The interesting biological activity associated with these natural products has not surprisingly prompted renewed interest in the synthesis of oxazoles. Although there are several methods available for the synthesis of oxazoles, this article focuses on just one route which has been used extensively in our own laboratory, namely that involving the reaction of diazocarbonyl compounds with niu'iles Scheme 1. Other aspects of diazocarbonyl chemistry have been widely reviewed.
The formation of oxazoles from nitriles and diazocarbonyl compounds was investigated by Huisgen in the early 's during his classic studies on 1,3-dipolar cycloaddition reactions. He and co-workers found that the ketocarbene derived from diazoacetophenone la by thermolysis at C underwent formal cycloaddition with benzonitrile giving a 0. The presence of electron withdrawing groups at the 2-position on the aromatic ring resulted in the formation of the oxazoles 2b and 2c in higher yield.
The yield of oxazole 2a was higher when the reaction was carried out in the presence of Cu acac 2. Huisgen et al. The authors found that the solvent had an effect on the rate of decomposition of ethyl diazoacetate; in the polar solvent, niu'obenzene, the rate was found to be twice that in the hydrocarbon solvent, decalin. Komendantov et al. In studies on 1-diazoketosulfones, Shioiri et al. One is the 4-sulfonyloxazole 7 whereas the other product 8 results from rearrangement and reaction with the alcohol.
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The ratio of products varies with the nature of the sulfone substituent with the benzyl group giving highest yields of oxazole Scheme 5. Sur, S. Arora, S. Kamakshi, R. Bayer, H. Azzolina, O. Kaur, R. Muthusamy, S. Quiroga, J. Jayashankaran, J. Xu, W. El-Rayyes, N. Wagner, G. Cummins, B. Dean, F. Fougerousse, A.
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