The scope and mechanism of phosphonium-mediated SNAr reactions in heterocyclic amides and ureas

ZK Wan, S Wacharasindhu, CG Levins…

Index: Wan, Zhao-Kui; Wacharasindhu, Sumrit; Levins, Christopher G.; Lin, Melissa; Tabei, Keiko; Mansour, Tarek S. Journal of Organic Chemistry, 2007 , vol. 72, # 26 p. 10194 - 10210

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Citation Number: 70

Abstract

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 ethers and thioethers using ...