2-膦亚胺叶立德-1,4-醌类衍生物的合成

Synthesis of 2-Phosphoranylidenamino-1,4-quinone Derivatives

膦亚胺叶立德是一类极其重要的有机膦试剂,在有机合成中通常被用作合成中间体和小分子催化剂。膦亚胺叶立德的合成主要是通过Staudinger反应来实现。醌类化合物具有良好的生理活性和独特的氧化还原性质,近年来,其官能化的研究取得了丰富的成果,但关于含有膦亚胺基团的醌类化合物的构建的研究较少。以1,4-醌类化合物为原料,经过3步反应,以中等到良好的总收率(56%~78%)得到了5种2-三苯基膦亚胺叶立德-1,4-醌类衍生物(4a~4e),其中化合物4b~4e为新型化合物,所有产物经^(1)H NMR,^(13)C NMR,^(31)P NMR和HR-MS(ESI)确证和表征。

Phosphinimides,a class of important organic phosphine reagents,are usually used as synthetic intermediates and small molecule catalysts in organic synthesis which were mainly synthesized by Staudinger reaction.Quinones have attracted the attention of researchers because of their good biological activities and unique redox properties.In recent years,the functionalization of quinones has achieved a series of results,but there are several reports on the construction of quinones containing phosphinimide groups.This paper reported that synthetic route of 2-phosphoranylidenamino-1,4-quinones was conducted with 1,4-quinones as starting materials via three steps.2-phosphoranylidenamino-1,4-quinone derivatives(4a~4e)were obtained in moderate to good overall yields(56%~78%),among them,compounds 4b~4e are new compounds.The products were confirmed and characterized by^(1)H NMR,^(13)C NMR,^(31)P NMR and HR-MS(ESI).