7464-55-3Relevant academic research and scientific papers
Cationic N-Heterocyclic Carbene Copper-Catalyzed [1,3]-Alkoxy Rearrangement of N-Alkoxyanilines
Nakamura, Itaru,Jo, Takeru,Ishida, Yasuhiro,Tashiro, Hiroki,Terada, Masahiro
supporting information, p. 3059 - 3062 (2017/06/23)
The [1,3]-alkoxy rearrangement reactions of N-alkoxyanilines were efficiently catalyzed by cationic N-heterocyclic carbene (NHC)-Cu catalysts in affording 2-alkoxyaniline derivatives in good to excellent yields with high functional group compatibility. For N-alkoxyanilines having an electron-withdrawing substituent at the meta-position, the alkoxy group selectively migrated to the more hindered ortho-position. In contrast, the alkoxy group migrated to the less hindered ortho-position for N-alkoxyanilines having an electron-donating substituent. Mechanistic studies suggest that the rearrangement reactions proceed via an intramolecular route.
Design and development of benzoxazole derivatives with toll-like receptor 9 antagonism
Roy, Swarnali,Mukherjee, Ayan,Paul, Barnali,Rahaman, Oindrila,Roy, Shounak,Maithri, Gundaram,Ramya, Bandaru,Pal, Sourav,Ganguly, Dipyaman,Talukdar, Arindam
, p. 334 - 347 (2017/04/26)
Toll-like receptor 9 (TLR9) is a major therapeutic target for numerous inflammatory disorders. Development of small molecule inhibitors for TLR9 remains largely empirical due to lack of structural understanding of potential TLR9 antagonism by small molecules and due to the unusual topology of the ligand binding surface of the receptor. To develop a structural model for rational design of small molecule TLR9 antagonists, an enhanced homology model of human TLR9 (hTLR9) was constructed. Binding mode analysis of a series of molecules having characteristic molecular geometry, flexibility and basicity was conducted based on crystal structure of the inhibitory DNA (iDNA) bound to horse and bovine TLR9. Interaction with specific amino acid residues in four leucine rich repeat (LRR) regions of TLR9 was identified to be critical for antagonism by small molecules. The biological validation of TLR9 antagonism and its correlation with probe-receptor interactions led to a reliable model that could be used for development of novel small molecules with potent TLR9 antagonism (IC50 30–100?nM) with excellent selectivity against TLR7.
The synthesis of N-arylated amides via copper(II) triflate-catalyzed direct oxygenation and N-arylation of benzylamines with aryl iodides
Xu, Mei,Zhang, Xiao-Hong,Shao, Yin-Lin,Han, Jiang-Sheng,Zhong, Ping
supporting information, p. 2665 - 2670,6 (2012/12/12)
An efficient approach for the synthesis of N-arylated amides by copper(II) triflate-catalyzed direct oxygenation and N-arylation reaction of benzylamines with aryl iodides is reported. Various benzylamines and aryl iodides can participate in the reaction, providing a series of N-arylated amides in moderate to good yields.
The synthesis of N-arylated amides via copper(II) triflate-catalyzed direct oxygenation and N-arylation of benzylamines with aryl iodides
Xu, Mei,Zhang, Xiao-Hong,Shao, Yin-Lin,Han, Jiang-Sheng,Zhong, Ping
supporting information, p. 2665 - 2670 (2013/01/15)
An efficient approach for the synthesis of N-arylated amides by copper(II) triflate-catalyzed direct oxygenation and N-arylation reaction of benzylamines with aryl iodides is reported. Various benzylamines and aryl iodides can participate in the reaction, providing a series of N-arylated amides in moderate to good yields.
Palladium-Imidazolium N-Heterocyclic Carbene-Catalyzed Carbonylative Amidation with Boronic Acids, Aryl Diazonium Ions, and Ammonia
Ma, Yudao,Song, Chun,Chai, Qiang,Ma, Changqin,Andrus, Merritt B.
, p. 2886 - 2889 (2007/10/03)
Aryl diazonium tetrafluoroborates have been coupled with arylboron compounds, carbon monoxide, and ammonia to give aryl amides in high yields. A saturated N-heterocyclic carbene (NHC) ligand, H2IPr was used with palladium(II) acetate to give the active catalyst. A mechanism is proposed for this novel four-component coupling reaction.
