70450-41-8Relevant articles and documents
Iminophosphorane-mediated regioselective umpolung alkylation reaction of α-iminoesters
Kukita, Mayu,Mino, Takashi,Omori, Kazuki,Sakamoto, Masami,Yoshida, Yasushi
, p. 4551 - 4564 (2021/05/31)
Umpolung reactions of imines, especially the asymmetric reactions, have been extensively studied as they provide access to important chiral amines in an efficient manner. The reactions studied range from simple Michael reactions to several kinds of other reactions such as the aza-benzoin reaction, aza-Stetter reaction, addition with MBH carbonate, and Ir-catalysed allylation. Herein, we report the first umpolung alkylation reaction of α-iminoesters with alkyl halides mediated by iminophosphorane as an organic superbase. The desired products were obtained in up to 82% yield with almost perfect regioselectivities. The key to the regioselectivity of this reaction was the use of 4-trifluoromethyl benzyl imines as a substrate. The products were successfully derivatised into the more functionalised molecules in good yields.
Bioisosteric Replacement of Arylamide-Linked Spine Residues with N-Acylhydrazones and Selenophenes as a Design Strategy to Novel Dibenzosuberone Derivatives as Type i 1/2 p38α MAP Kinase Inhibitors
Pedreira, Júlia G. B.,Nahidino, Philipp,Kudolo, Mark,Pantsar, Tatu,Berger, Benedict-Tilman,Forster, Michael,Knapp, Stefan,Laufer, Stefan,Barreiro, Eliezer J.
supporting information, p. 7347 - 7354 (2020/09/11)
The recent disclosure of type I 1/2 inhibitors for p38α MAPK demonstrated how the stabilization of the R-spine can be used as a strategy to greatly increase the target residence time (TRT) of inhibitors. Herein, for the first time, we describe N-acylhydrazone and selenophene residues as spine motifs, yielding metabolically stable inhibitors with high potency on enzymatic, NanoBRET, and whole blood assays, improved metabolic stability, and prolonged TRT.
Catalytic Halogen Bond Activation in the Benzylic C-H Bond Iodination with Iodohydantoins
Combe, Sascha H.,Hosseini, Abolfazl,Song, Lijuan,Hausmann, Heike,Schreiner, Peter R.
supporting information, p. 6156 - 6159 (2017/11/24)
This letter presents the side-chain iodination of electron-deficient benzylic hydrocarbons at rt using N-hydroxyphthalimide (NHPI) as radical initiator and 1,3-diiodo-5,5-dimethylhydantoin and 3-iodo-1,5,5-trimethylhydantoin (3-ITMH) as iodine source. Addition of a carboxylic acid increased the reactivity due to complex formation with and activation of 3-ITMH by proton transfer and halogen bond formation. No SEAr reactions were observed under the employed reaction conditions. Our method enables convenient product isolation and gives 50-72% yields of isolated products.
