<i>N</i>-Sulfonyl acetylketenimine as a highly reactive intermediate for the synthesis of <i>N</i>-sulfonyl amidines
作者:Weiguang Yang、Dayun Huang、Xiaobao Zeng、Dongping Luo、Xinyan Wang、Yuefei Hu
DOI:10.1039/c8cc04699a
日期:——
A highly reactive intermediate N-sulfonyl acetylketenimine was generated from a 3-butyn-2-one participating CuAAC/ring-opening method. Its high reactivity due to bearing two EWGs allowed us to offer the first example of a reaction between ketenimine and amide to synthesize N-sulfonyl amidines efficiently.
A facile method for the synthesis of tetrasubstituted N-sulfonylguanidines has been developed via the direct condensation of sulfonamides and ureas in the presence of phosphoryl chloride under basic conditions. Detailed synthetic studies showed that this is a simple protocol for preparing N-sulfonylguanidines at room temperature in a short reaction time with good to excellent yields. Graphic abstract
The synthesis of sulfonylguanidines from N,N,N',N'-tetramethylthiourea and sulfonyl azides is described. This method serves as an alternative route for generating sulfonylguanidines via the use of stable starting materials.