7006-52-2Relevant articles and documents
Synthesis of 4-functionalized indoles via benzyne cyclization of N-(2- lithioallyl)-2-fluoroanilines
Barluenga, Jose,Fananas, Francisco J.,Sanz, Roberto,Fernandez, Yolanda
, p. 1049 - 1052 (1999)
Treatment of N-(2-bromoallyl)-N-methyl-2-fluoroaniline with tert- butyllithium affords 1,3-dimethyl-4-lithioindole, via intramolecular addition to a tethered benzyne intermediate. Further reaction with electrophiles leads to 4-functionalized 3-methylindol
Iodine-Promoted Metal-Free Cyclization and O/S Exchange of Acrylamides with Thiuram: One-Step Synthesis of Quinolino-2-thiones
Jiao, Jing,Wang, Cheng,Xiao, Fangtao,Zhang, Zhipeng
supporting information, (2022/04/07)
A one-step cyclization and O/S exchange reaction of readily available acrylamides in the presence of iodine and thiuram has been developed. The reaction provides an efficient approach for the synthesis of highly important heterocycle quinolino-2-thiones with diverse substitution patterns.
Additive-freeN-methylation of amines with methanol over supported iridium catalyst
Liu, Xiang,Loh, Teck-Peng,Qiang, Wenwen,Wang, Jing,Ye, Sen,Zhu, Longfei
, p. 3364 - 3375 (2021/06/06)
An efficient and versatile zinc oxide-supported iridium (Ir/ZnO) catalyst was developed to catalyze the additive-freeN-methylation of amines with methanol. Mechanistic studies suggested that the high catalytic reactivity is rooted in the small sizes (1.4 nm) of Ir nanoparticles and the high ratio (93%) of oxidized iridium species (IrOx, Ir3+and Ir4+) on the catalyst. Moreover, the delicate cooperation between the IrOxand ZnO support also promoted its high reactivity. The selectivity of this catalyticN-methylation was controllable between dimethylation and monomethylation by carefully tuning the catalyst loading and reaction solvent. Specifically, neat methanol with high catalyst loading (2 mol% Ir) favored the formation ofN,N-dimethylated amine, while the mesitylene/methanol mixture with low catalyst loading (0.5 mol% Ir) was prone to producing mono-N-methylated amines. An environmentally benign continuous flow system with a recycled mode was also developed for the efficient production ofN-methylated amines. With optimal flow rates and amine concentrations, a variety ofN-methylamines were produced with good to excellent yields in this Ir/ZnO-based flow system, providing a starting point for the clean and efficient production ofN-methylamines with this cost-effective chemical process.