A New Convenient Preparation of 2-, 4-, and 5- Thiazolecarboxaldehydes and Their Conversion into the Corresponding Carbonitrile<i>N</i>-Oxides: Synthesis of 3-Thiazolylisoxazoles and 3-Thiazolylisoxazolines
作者:Alessandro Dondoni、Giancarlo Fantin、Marco Fogagnolo、Alessandro Medici、Paola Pedrini
DOI:10.1055/s-1987-28146
日期:——
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
标题醛类化合物通过淬灭2-锂噻唑、4-锂-和5-锂-2-三甲基硅基噻唑与N-甲酰吗啉来制备,产率较高。在后两种情况下,随后进行脱硅化处理。这些醛类化合物通过其肟和羟肟酰氯转化为氰化物,与烯烃和乙炔二极亲电试剂反应,以中等至良好产率得到3-噻唑基异恶唑啉和3-噻唑基异恶唑。