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Synthesis 1987; 1987(11): 998-1001
DOI: 10.1055/s-1987-28146
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A New Convenient Preparation of 2-, 4-, and 5- Thiazolecarboxaldehydes and Their Conversion into the Corresponding Carbonitrile N-Oxides: Synthesis of 3-Thiazolylisoxazoles and 3-Thiazolylisoxazolines

Alessandro Dondoni* , Giancarlo Fantin, Marco Fogagnolo, Alessandro Medici, Paola Pedrini
  • *Dipartimento di Chimica, Laboratorio di Chimica Organica, Università di Ferrara, via L. Borsari 46, I-44100 Ferrara, Italy
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Publication History

Publication Date:
12 September 2002 (online)

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The title aldehydes are prepared in high Yieids by quenching 2-lithiothiazole, 4-litho-, and 5-litho-2-trimethylsilylthiazole with N-formylmorpholine followed by protodesilylation in the latter two cases. The aldehydes are transformed through their oximes and hydroxamoyl chlorides into nitrile oxides which react with alkene and acetylene dipolarophiles to give 3-thiazolylisoxazolines and 3-thiazolylisoxazoles in moderate to good yields