16347-97-0Relevant articles and documents
Hexachlorocyclotriphosphazene (HCCP)-mediated direct formation of thioethers and ethers from quinazolin-4(3H)-ones
Hu, Baoxiang,Zhang, Xiaochu,Sheng, Lili,Guo, Ming,Shen, Zhenlu,Hu, Xinquan,Sun, Nan,Mo, Weimin
, p. 5580 - 5593 (2013/07/04)
A hexachlorocyclotriphosphazene (HCCP)-mediated direct formation of quinazoline (thio)ethers from quinazolin-4(3H)-ones has been developed. Treatment of quinazolin-4(3H)-ones with HCCP, diisopropylethylamine (DIPEA), and thiophenols resulted in formation of the corresponding 4-arylthioquinazoline derivatives in moderate to excellent yields. This method has also been utilized to prepare 4-aryloxyquinazoline and 4-alkoxyquinazoline derivatives using phenols and sodium alkoxides as the nucleophiles.
Hydrogen peroxide mediated formation of heteroaryl ethers from pyridotriazol-1-yloxy heterocycles and arylboronic acids
Bardhan, Sujata,Tabei, Keiko,Wan, Zhao-Kui,Mansour, Tarek S.
supporting information; experimental part, p. 5733 - 5736 (2009/12/06)
Pyridotriazol-1-yloxypyrimidine 3 reacts with arylboronic acids under palladium-free, Cs2CO3, (0.8%) H2O2, and DME conditions to produce heteroaryl ethers 4-16 in good yields comparable to the oxidative palladiu
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.