123158-66-7Relevant 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
supporting information, p. 8018 - 8023 (2019/05/29)
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.
Kynurenic acid derivatives useful in the treatment of neurodegenerative disorders
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, (2008/06/13)
4-Oxo-1,4-dihydroquinoline compounds having a 2-acidic group or a group convertible thereto in vivo, and their pharmaceutically acceptable salts, are potent specific antagonists of N-methyl-D-aspartate (NMDA) receptors and are therefore useful in the treatment of neurodegenerative disorders. 4-Oxo-1,4-dihydroquinoline compounds having a 2-acidic group or a group convertible thereto in vivo, other than carboxy or C 1-6 alkoxycarbonyl, are novel compounds, as also are compounds of formula II STR1 wherein R 2 represents carboxy or a group convertible thereto in vivo, R 6 is hydrogen and R 5 and R 7 represent C 1-6 alkyl or halogen, provided that R 5 and R 7 are not simultaneously chlorine or simultaneously bromine; a process for preparing the novel compounds is described, as also are pharmaceutical compositions containing the novel compounds.