33224-19-0Relevant academic research and scientific papers
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.
Preparation technology of 3-cyano-5-anisole-1-sulfonyl chloride
-
, (2018/03/26)
The invention discloses a preparation technology of 3-cyano-5-anisole-1-sulfonyl chloride. The technology comprises the following steps: performing substitution reaction on a raw material which is 3,5-dinitrobenzene to obtain 3-anisyl-5-nitrobenzoic acid;
Synthesis of Unlabelled and Carboxyl-Labelled 3-Amino-5-hydroxybenzoic Acid
Herlt, Anthony J.,Kibby, Jeffrey J.,Rickards, Rodney W.
, p. 1319 - 1324 (2007/10/02)
Efficient syntheses are reported of the natural amino acid 3-amino-5-hydroxybenzoic acid in unlabelled and carboxyl-labelled forms from 3,5-dinitrobenzoic acid and 3,5-dinitroanisole, respectively.
