The Scope and Mechanism of Phosphonium-Mediated S<sub>N</sub>Ar Reactions in Heterocyclic Amides and Ureas
作者:Zhao-Kui Wan、Sumrit Wacharasindhu、Christopher G. Levins、Melissa Lin、Keiko Tabei、Tarek S. Mansour
DOI:10.1021/jo7020373
日期:2007.12.1
An efficient “one-step” synthesis of cyclic amidines and guanidines has been developed. Treatment of cyclic amides and ureas with benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP), base, and nitrogen nucleophiles leads to the formation of the corresponding cyclic amidines and guanidines, typically in good to excellent yields. This method has also been used to prepare heteroaryl
已经开发了有效的“一步”合成环状am和胍的方法。用六氟磷酸苯并三唑-1-基氧基三(二甲氨基)phosph,碱和氮亲核试剂处理环状酰胺和脲会导致形成相应的环状typically和胍,通常收率高至优异。该方法也已经用于使用苯酚和硫代苯酚亲核试剂制备杂芳基醚和硫醚。时程NMR和HPLC-MS研究促进了所提出的中间体(phospho盐和HOBt加合物)的明确表征。数据揭示了逐步的反应途径。