718-30-9Relevant academic research and scientific papers
Aromatic Aza-Claisen Rearrangement of Arylpropargylammonium Salts Generated in situ from Arynes and Tertiary Propargylamines
Han, Lu,Li, Sheng-Jun,Zhang, Xue-Ting,Tian, Shi-Kai
supporting information, p. 3091 - 3097 (2021/01/21)
The charge-accelerated aza-Claisen rearrangement of ammonium salts serves as a key step in the construction of complex nitrogen-containing molecules. However, much less attention has been paid to the aromatic aza-Claisen rearrangement than to the aliphatic one. Herein, we report an unprecedented aromatic aza-Claisen rearrangement of arylpropargylammonium salts, generated in situ from arynes and tertiary propargylamines, delivering structurally diverse 2-propargylanilines in moderate to good yields with high regioselectivity. This rearrangement proceeds in the absence of strong bases or transition metals, is compatible with moisture and air, tolerates a wide variety of functional groups, and is amenable to forming 11- to 13-membered heterocycles with a triple bond. The 2-propargylaniline products were treated with aluminum chloride in ethanol to afford multisubstituted indoles in moderate to excellent yields. Finally, a series of deuterium-labeling experiments was performed to elucidate the reaction mechanism.
Aminoalkylation with aldehydes mediated by solid lithium perchlorate
Saidi, Mohammad R.,Nazari, Mohammad
, p. 309 - 312 (2007/10/03)
The solid LiClO4-mediated one-pot reaction of aldehydes with secondary amines and C nucleophiles afforded the corresponding aminoalkylation products in high yields. Unlike the previous reported procedure, the aminoalkylation of aldehyde was achieved in the presence of only 0.5 equivalents of solid lithium perchlorate in dichloromethane as the solvent with good to high yields at room temperature. Springer-Verlag 2003.
Three component aminoalkylation of aldehydes by functionalized organozinc compounds promoted by lithium perchlorate (LiClO4)
Saidi, Mohammad R.,Khalaji, Hamid R.,Ipaktschi, Junes
, p. 1983 - 1986 (2007/10/03)
The one-pot synthesis of several N,N-dialkylamino esters is reported. Treatment of aldehydes 1 (aliphatic and aromatic) with (trimethylsilyl)dialkylamines 2, in the presence of LiClO4 in diethyl ether presumably gives the intermediates 3. Reaction of these intermediates 3 with functionalized organozinc reagents, RZnBr, produces a variety of N,N-dialkylamino esters in a short time (about 1 h) and in good to moderate yields. The pure products are isolated by extraction with cold hydrochloric acid.
