569315-05-5Relevant articles and documents
Visible-Light-Induced Oxazoline Formations fromN-Vinyl Amides Catalyzed by an Ion-Pair Charge-Transfer Complex
Sun, Rui,Yang, Xiao,Ge, Yicen,Song, Jintong,Zheng, Xueli,Yuan, Maolin,Li, Ruixiang,Chen, Hua,Fu, Haiyan
, p. 11762 - 11773 (2021/09/28)
Visible-light photoredox catalysis plays an important role in various reactions which are inaccessible under typical thermal conditions. Distinctly different from common visible-light photoredox catalysis which often involves transition-metal complexes, conjugated organic dyes, or electron donor-acceptor complexes, herein, the use of ion-pair charge-transfer (IPCT) complex-induced visible-light photoredox catalytic reactions are described, wherein the cyclization-methoxylation ofN-vinyl amides in methanol was achieved under irradiation with blue LEDs. The reaction employs a heteroarenium iodide as the photocatalyst and can be extended to cyclization-alkoxylation, ?acyloxylation, and ?hydroxylation. This protocol provides an eco-friendly synthetic route to a wide range of oxazoline derivatives. Mechanistic investigations with UV-visible spectroscopy and control experiments confirm the existence of the IPCT absorption band in the visible region for the heteroarenium iodide, which is responsible for the observed reactivity.
Facile Synthesis of Substituted 4-Alkoxy-2-oxazolines and Exploration of the Reaction Mechanism
Zhu, Jianming,Li, Xiaolong,Wang, Guimin,Li, Bo,Xu, Zhijian,Tian, Shikai,Hall, Adrian,Shen, Jingshan,Shi, Jiye,Zhu, Weiliang
, p. 1331 - 1343 (2016/05/02)
Substituted 4-alkoxy-2-oxazolines have been synthesized via the reaction of nitriles with beta-hydroxyacetals promoted by trifluoromethanesulfonic acid. The reaction is proposed to be initiated by the protonation of the acetals to produce carbocations tha
Anodic methoxylation and acetoxylation of imines and imidates
Baba, Daisuke,Fuchigami, Toshio
, p. 3133 - 3136 (2007/10/03)
Anodic oxidation of cyclic imidates, 2-aryl-2-oxazolines, in methanol provided the corresponding 4-methoxylated products. Anodic α-methoxylation and α-acetoxylation of open-chain imines derived from glycine esters and benzophenone were also achieved using a bromide ion mediator. On the other hand, anodic α-acetoxylation of CF3-containing imine and imidate was successful without use of the bromine mediator. This is the first example of successful anodic α-substitution of imines and imidates.