1025718-78-8Relevant articles and documents
meta-Nitration of Arenes Bearing ortho/para Directing Group(s) Using C?H Borylation
Li, Xuejing,Deng, Xingwang,Coyne, Anthony G.,Srinivasan, Rajavel
, p. 8018 - 8023 (2019)
Herein, we report the meta-nitration of arenes bearing ortho/para directing group(s) using the iridium-catalyzed C?H borylation reaction followed by a newly developed copper(II)-catalyzed transformation of the crude aryl pinacol boronate esters into the corresponding nitroarenes in a one-pot fashion. This protocol allows the synthesis of meta-nitrated arenes that are tedious to prepare or require multistep synthesis using the existing methods. The reaction tolerates a wide array of ortho/para-directing groups, such as ?F, ?Cl, ?Br, ?CH3, ?Et, ?iPr ?OCH3, and ?OCF3. It also provides regioselective access to the nitro derivatives of π-electron-deficient heterocycles, such as pyridine and quinoline derivatives. The application of this method is demonstrated in the late-stage modification of complex molecules and also in the gram-scale preparation of an intermediate en route to the FDA-approved drug Nilotinib. Finally, we have shown that the nitro product obtained by this strategy can also be directly converted to the aniline or hindered amine through Baran's amination protocol.
Stereoselective Synthesis of New (2 S,3 R)-3-Carboxyphenyl)pyrrolidine-2-carboxylic Acid Analogues Utilizing a C(sp3)-H Activation Strategy and Structure-Activity Relationship Studies at the Ionotropic Glutamate Receptors
Bunch, Lennart,Hansen, Jacob C.,Hansen, Kasper B.,Iliadis, Stylianos,Kayser, Silke,Krogsgaard-Larsen, Niels,Larsen, Younes,Moroz, Aleksandra,Nielsen, Birgitte,Pickering, Darryl S.,Staudt, Markus,Syrenne, Jed T.,Temperini, Piero,Yi, Feng
, (2020/03/10)
Competitive antagonists for ionotropic glutamate receptors (iGluRs) are highly valuable tool compounds for studying health and disease states in the central nervous system. However, only few subtype selective tool compounds are available and the discovery of antagonists with novel iGluR subtype selectivity profiles remains a profound challenge. In this paper, we report an elaborate structure-activity relationship (SAR) study of the parental scaffold 2,3-trans-3-carboxy-3-phenyl-proline by the synthesis of 40 new analogues. Three synthetic strategies were employed with two new strategies of which one being a highly efficient and fully enantioselective strategy based on C(sp3)-H activation methodology. The SAR study led to the conclusion that selectivity for the NMDA receptors was a general trend when adding substituents in the 5′-position. Selective NMDA receptor antagonists were obtained with high potency (IC50 values as low as 200 nM) and 3-34-fold preference for GluN1/GluN2A over GluN1/GluN2B-D NMDA receptors.
Synthesis of diverse 3-azido-5-(azidomethyl)benzene derivatives via formal C-H azidation and functional group-selective transformations
Nishiyama, Yoshitake,Misawa, Yoshihiro,Hazama, Yuki,Oya, Kazuhiro,Yoshida, Suguru,Hosoya, Takamitsu
, p. 1053 - 1072 (2019/07/31)
3-Azido-5-(azidomethyl)benzene derivatives are useful compounds for preparing diverse bistriazole compounds and photoaffinity probes for target identification of bioactive compounds. To more easily synthesize a diverse range of diazido compounds, a facile
