Journal of Taibah University for Science ( IF 3.3 ) Pub Date : 2020-06-09 , DOI: 10.1080/16583655.2020.1777782 R. Udhayasurian 1, 2 , K. Sivakumar 3 , Ayyiliath M. Sajith 4 , Muthipeedika Nibin Joy 5
We herein report a modified approach for the synthesis of some pharmacologically relevant oxazole derivatives linked with amides under mild conditions. The utilization of polymer-supported triphenylphosphine (poly-TPP) as a phosphine ligand for generating the key iminophosphorane intermediate was found to be vital for achieving the synthesis of oxazole in room temperature. This alternative approach relying on the cyclization reaction of readily available phenacyl azide and phenyl isothiocyanate rendered the oxazole derivative 3a in excellent yield. This methodology has been applied for the synthesis of a more decorated oxazole derivative 3b having ester functionality and was further converted to different amides under microwave irradiation in good to excellent yields in the later stage.
中文翻译:
在温和条件下合成生物学相关的5-取代的-2-N-芳基-1,3-恶唑衍生物的改进方法
我们在本文中报道了在温和条件下与酰胺连接的一些药理学相关的恶唑衍生物的合成的改进方法。已发现利用聚合物负载的三苯膦(poly-TPP)作为膦配体来生成关键的亚氨基膦烷中间体对于在室温下完成恶唑的合成至关重要。该替代方法依赖于容易获得的苯甲酰基叠氮化物和异硫氰酸苯酯的环化反应,从而使恶唑衍生物3a具有优异的收率。该方法已用于合成装饰性更高的恶唑衍生物3b 具有酯官能团的产物,并在随后的微波辐射下以良好至优异的产率进一步转化为不同的酰胺。