4040-08-8Relevant academic research and scientific papers
The scope and mechanism of phosphonium-mediated SNAr reactions in heterocyclic amides and ureas
Wan, Zhao-Kui,Wacharasindhu, Sumrit,Levins, Christopher G.,Lin, Melissa,Tabei, Keiko,Mansour, Tarek S.
, p. 10194 - 10210 (2008/04/12)
(Chemical Equation Presented) An efficient "one-step" synthesis of cyclic amidines and guanidines has been developed. Treatment of cyclic amides and ureas with benzotriazol-l-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 ethers and thioethers using phenol and thiophenol nucleophiles. Time course NMR and HPLC-MS studies have facilitated explicit characterization of the proposed intermediates (the phosphonium salt and HOBt adduct); the data reveal a stepwise reaction pathway.
An efficient direct amination of cyclic amides and cyclic ureas
Wan, Zhao-Kui,Wacharasindhu, Sumrit,Binnun, Eva,Mansour, Tarek
, p. 2425 - 2428 (2007/10/03)
An efficient one-step amination of cyclic amides and ureas has been developed. Treatment of cyclic amides and cyclic ureas with BOP in the presence of DBU in various solvents led to the formation of cyclic amidines and cyclic guanidines in good to excellent yields. Concise syntheses of biologically intriguing kinetin and potent kinase inhibitor olomoucin were thus achieved in just one and two steps, respectively.
