195141-05-0Relevant academic research and scientific papers
Photoreductive Removal of O-Benzyl Groups from Oxyarene N-Heterocycles Assisted by O-Pyridine-pyridone Tautomerism
Todorov, Aleksandar R.,Wirtanen, Tom,Helaja, Juho
, p. 13756 - 13767 (2017/12/26)
Facile photoreductive protocols have been developed to remove benzyl O-protective groups from oxyarene N-heterocycles at positions capable for 2-/4-O-pyridine-2-/4-pyridone tautomerism. Blue light irradiation, a [Ru] or [Ir] photocatalyst, and ascorbic acid in a water-acetonitrile solution debenzylates a variety of aryl N-heterocycles cleanly and selectively. Ascorbic acid has two functions in the reaction. On the one hand, it protonates the N-heterocycles that reduces their reduction potentials notably and on the other hand it acts as a sacrificial reductant. Reduction potentials and free energy barriers calculated at the CPCM-B3LYP/6-31+G? level can predict the reactivities of the studied substrates.
A Direct C2-Selective Phenoxylation and Alkoxylation of Quinoline N-Oxides with Various Phenols and Alcohols in the Presence of H-Phosphonate
Bi, Wen-Zhu,Qu, Chen,Chen, Xiao-Lan,Qu, Ling-Bo,Liu, Zhi-Dong,Sun, Kai,Li, Xu,Zhao, Yu-Fen
supporting information, p. 5125 - 5130 (2017/09/22)
A practical and efficient method for the synthesis of 2-aroxy(alkoxy)quinolines has been developed by direct cross-dehydrogenative coupling reaction between quinoline N-oxides and readily available phenols and alcohols in the presence of H-phosphonate and
Synthesis of substituted N-benzyl pyridones via an O- To N-alkyl migration
Lanni, Erica L.,Bosscher, Michael A.,Ooms, Bartel D.,Shandro, Christina A.,Ellsworth, Bruce A.,Anderson, Carolyn E.
, p. 6425 - 6428 (2008/12/21)
(Chemical Equation Presented) A new LiI-promoted O- to N-alkyl migration has been developed for the conversion of O-alkylated 2-hydroxy pyridines, quinolines, and pyrimidines to the corresponding N-alkylated heterocycles in good to excellent yields (57-99%). This method serves as an efficient means for the preparation of N-benzyl pyridones, quinolones, and pyrimidones.
