896156-54-0Relevant academic research and scientific papers
Diversification of edaravone via palladium-catalyzed hydrazine cross-coupling: Applications against protein misfolding and oligomerization of beta-amyloid
Maclean, Mark A.,Diez-Cecilia, Elena,Lavery, Christopher B.,Reed, Mark A.,Wang, Yanfei,Weaver, Donald F.,Stradiotto, Mark
supporting information, p. 100 - 104 (2015/12/18)
N-Aryl derivatives of edaravone were identified as potentially effective small molecule inhibitors of tau and beta-amyloid aggregation in the context of developing disease-modifying therapeutics for Alzheimer's disease (AD). Palladium-catalyzed hydrazine monoarylation protocols were then employed as an expedient means of preparing a focused library of 21 edaravone derivatives featuring varied N-aryl substitution, thereby enabling structure-activity relationship (SAR) studies. On the basis of data obtained from two functional biochemical assays examining the effect of edaravone derivatives on both fibril and oligomer formation, it was determined that derivatives featuring an N-biaryl motif were four-fold more potent than edaravone.
Mild and rapid Pd-catalyzed cross-coupling with hydrazine in continuous flow: Application to the synthesis of functionalized heterocycles
Deangelis, Andrew,Wang, Dong-Hui,Buchwald, Stephen L.
supporting information, p. 3434 - 3437 (2013/05/09)
Minimizing risk: The synthesis of arylhydrazines through C?￡?N cross-coupling of aryl chlorides with hydrazine is described. Through the use of continuous flow, the hazards associated with the use of hydrazine in the presence of transition metals are decreased. In addition, multistep flow sequences have also been developed for the generation of functionalized heterocycles utilizing the arylhydrazine intermediates.
Palladium-catalyzed cross-coupling of aryl chlorides and tosylates with hydrazine
Lundgren, Rylan J.,Stradiotto, Mark
supporting information; experimental part, p. 8686 - 8690 (2011/01/08)
Hydrazine is not a problem anymore: The title transformation is the first reaction to yield aryl hydrazines through the cross-coupling of aryl chlorides and tosylates with hydrazine. An appropriately designed palladium catalyst allows this reaction to proceed rapidly under mild conditions, and with excellent chemoselectivity (see scheme; Ad=adamantyl, Ts=4-toluenesulfonyl).
