62289-81-0Relevant academic research and scientific papers
Efficient and Mild Ullmann-Type N-Arylation of Amides, Carbamates, and Azoles in Water
Bollenbach, Maud,Aquino, Pedro G. V.,de Araújo-Júnior, Jo?o Xavier,Bourguignon, Jean-Jacques,Bihel, Frédéric,Salomé, Christophe,Wagner, Patrick,Schmitt, Martine
supporting information, p. 13676 - 13683 (2017/10/10)
A simple, sustainable, efficient, mild, and low-cost protocol was developed for d-glucose-assisted Cu-catalyzed Ullmann reactions in water for amides, carbamates, and nitrogen-containing heterocycles. The reaction was compatible with diverse aryl/heteroaryl iodides, giving highly substituted pyridine, indole, or indazole rings. This method offers an attractive alternative to existing protocols, because the reaction proceeds in aqueous media, occurs at or near ambient temperature, and provides the N-arylated products in good to high yields.
Pd-catalyzed amidations of aryl chlorides using monodentate biaryl phosphine ligands: A kinetic, computational, and synthetic investigation
Ikawa, Takashi,Barder, Timothy E.,Biscoe, Mark R.,Buchwald, Stephen L.
, p. 13001 - 13007 (2008/09/17)
We present results on the amidation of aryl halides and sulfonates utilizing a monodentate biaryl phosphine-Pd catalyst. Our results are in accord with a previous report that suggests that the formation of κ2- amidate complexes is deleterious to the effectiveness of a catalyst for this transformation and that their formation can be prevented by the use of appropriate bidentate ligands. We now provide data that suggest that the use of certain monodentate ligands can also prevent the formation of the κ2-amidate complexes and thereby generate more stable catalysts for the amination of aryl chlorides. Furthermore, computational studies shed light on the importance of the key feature(s) of the biaryl phosphines (a methyl group ortho to the phosphorus center) that enable the coupling to occur. The use of ligands that possess a methyl group ortho to the phosphorus center allows a variety of aryl and heteroaryl chlorides with various amides to be coupled in high yield.
Design, synthesis, and evaluation of inhibitors for severe acute respiratory syndrome 3C-like protease based on phthalhydrazide ketones or heteroaromatic esters
Zhang, Jianmin,Pettersson, Hanna I.,Huitema, Carly,Niu, Chunying,Yin, Jiang,James, Michael N. G.,Eltis, Lindsay D.,Vederas, John C.
, p. 1850 - 1864 (2008/02/02)
The 3C-like protease (3CLpro), which controls the severe acute respiratory syndrome (SARS) coronavirus replication, has been identified as a potential target for drug design in the treatment of SARS. A series of tetrapeptide phthalhydrazide ketones, pyridinyl esters, and their analogs have been designed, synthesized, and evaluated as potential SARS 3CLpro inhibitors. Some pyridinyl esters are identified as very potent inhibitors, with IC50 values in the nanomolar range (50-65 nM). Electrospray mass spectrometry indicates a mechanism involving acylation of the active site cysteine thiol for this class of inhibitors.
