Details

Autor(en) / Beteiligte

• Wan, Zhao-Kui
• Wacharasindhu, Sumrit
• Levins, Christopher G
• Lin, Melissa
• Tabei, Keiko
• Mansour, Tarek S

Titel

The Scope and Mechanism of Phosphonium-Mediated SNAr Reactions in Heterocyclic Amides and Ureas

Ist Teil von

• Journal of organic chemistry, 2007-12, Vol.72 (26), p.10194-10210

Ort / Verlag

Washington, DC: American Chemical Society

Erscheinungsjahr

2007

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• 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 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.