51089-06-6Relevant articles and documents
Highly Selective Difluoromethylations of β-Keto Amides with -TMSCF 2Br under Mild Conditions
Chen, Pengli,Fu, Yang,Hu, Yanqin,Wang, Shuaifei,Wang, Yakun,Zhang, Conghui,Zhang, Mingwei,Zhao, Ting
, p. 1123 - 1130 (2021/06/18)
Without employing any transition metal and other additives, efficient methods for selective difluoromethylations of β-keto amides with TMSCF 2 Br reagent have been developed under mild conditions. This protocol allows a convenient access to various α-difluoromethyl β-keto amides with excellent yields (up to 93%) and high carbon/oxygen (C/O) regioselectivities (up to 99:1). The C/O selectivity of β-keto amides could be easily reversed and controlled by simply changing the base. This protocol can be easily scaled-up and the C-difluoromethylation product could be reduced into CF 2 H-containing amino alcohol derivatives. Moreover, the first enantioselective electrophilic difluoromethylation of β-keto amides has been achieved by phase-transfer catalysis.
A Chiral Phenanthroline Ligand with a Hydrogen-Bonding Site: Application to the Enantioselective Amination of Methylene Groups
Annapureddy, Rajasekar Reddy,Jandl, Christian,Bach, Thorsten
supporting information, p. 7374 - 7378 (2020/08/06)
A silver-catalyzed amination is reported that occurs at the aliphatic C3-substituent of various quinolones and pyridones. The C-H amination reaction proceeded with high site-and enantioselectivity (14 examples, 83-97% ee). The key to its success is the use of a chiral phenanthroline ligand that is attached via an ethynyl linker to the 8-position of octahydro-1H-4,7-methanoisoindol-1-one. AgPF6 (10 mol %) served as the silver source, PhI.NNs as the nitrene precursor, and 1,10-phenanthroline as the coligand. The reaction outcome can be understood by assuming a nitrene C-H insertion within a hydrogen-bonded silver complex in which a single C-H bond is exposed to the catalytic reaction center.
4-Alkyl- and 3,4-dialkyl-1,2,3,4-tetrahydro-8-pyridono[5,6- g]quinolines: Potent, nonsteroidal androgen receptor agonists
Higuchi, Robert I.,Edwards, James P.,Caferro, Thomas R.,Ringgenberg, Josef D.,Kong, James W.,Hamann, Lawrence G.,Arienti, Kristen L.,Marschke, Keith B.,Davis, Robert L.,Farmer, Luc J.,Jones, Todd K.
, p. 1335 - 1340 (2007/10/03)
A series of human androgen receptor (hAR) agonists based on 4-alkyl-; 4,4-dialkyl-; and 3,4-dialkyl-1,2,3,4-tetrahydro-8-pyridono[5,6-g]quinoline was synthesized and evaluated in competitive receptor binding assays and an androgen receptor cotransfection assay in a mammalian cell background. A number of compounds in this series demonstrated activity equal to or better than dihydrotestosterone in both assays and represent a novel class of compounds for use in androgen replacement therapy.