5411-50-7Relevant 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.
PROCESS FOR THE PREPARATION OF ORGANIC HALIDES
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Paragraph 00139, (2017/08/01)
The present invention provides a halo-de-carboxylation process for the preparation of organic chlorides, organic bromides and mixtures thereof, from their corresponding carboxylic acids, using a chlorinating agent selected from trichloroisocyanuric acid (TCCA), dichloroisocyanuric acid (DCCA), or combination thereof, and a brominating agent.
PROCESS FOR THE PREPARATION OF ORGANIC BROMIDES
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Paragraph 00164, (2017/07/28)
The present invention provides a process for the preparation of organic bromides, by a radical bromodecarboxylation of carboxylic acids with a bromoisocyanurate.
Site-specific cleavage of nucleic acids by photoreactive conjugates
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Page/Page column 3, (2012/08/28)
A process of forming a double strand cleavage in DNA includes providing a reaction mixture containing double stranded DNA having a break in a first strand defining a target site in a second strand. The method continues by adding to the reaction mixture a
Synthesis and biological evaluation of piperazinyl heterocyclic antagonists of the gonadotropin releasing hormone (GnRH) receptor
Vera, Matthew D.,Lundquist IV, Joseph T.,Chengalvala, Murty V.,Cottom, Joshua E.,Feingold, Irene B.,Garrick, Lloyd M.,Green, Daniel M.,Hauze, Diane B.,Mann, Charles W.,Mehlmann, John F.,Rogers, John F.,Shanno, Linda,Wrobel, Jay E.,Pelletier, Jeffrey C.
supporting information; scheme or table, p. 2512 - 2515 (2010/07/06)
Antagonism of the gonadotropin releasing hormone (GnRH) receptor has resulted in positive clinical results in reproductive tissue disorders such as endometriosis and prostate cancer. Following the recent discovery of orally active GnRH antagonists based on a 4-piperazinylbenzimidazole template, we sought to investigate the properties of heterocyclic isosteres of the benzimidazole template. We report here the synthesis and biological activity of eight novel scaffolds, including imidazopyridines, benzothiazoles and benzoxazoles. The 2-(4-tert-butylphenyl)-8-(piperazin-1-yl)imidazo[1,2-a]pyridine ring system was shown to have nanomolar binding potency at the human and rat GnRH receptors as well as functional antagonism in vitro. Additional structure-activity relationships within this series are reported along with a pharmacokinetic comparison to the benzimidazole-based lead molecule.
Benzofused N-substituted cyclic enediynes: Activation and DNA-cleavage potential
Basak, Amit,Kar, Moumita
, p. 4532 - 4537 (2008/12/20)
The effect of electron withdrawal on the reactivity of N-substituted cyclic enediynes has been studied. These were synthesized via an intramolecular Mitsunobu reaction. The electron withdrawing effect of the nitro groups or the positive charge on the free
Electrochemical fluorination of aromatic compounds in anhydrous HF
Shainyan,Danilevich
, p. 214 - 219 (2007/10/03)
Electrochemical fluorination of anisole furnished 2- and 4-fluoroanisoles in a 3:1 ratio, guaiacol, and 4,4′-dimethoxydiphenyl ether. Phenylacetonitrile alongside the fluorination in the ring suffered the transformation of the cyano group into a trifluoromethyl. 4-Bromobenzamide was fluorinated to a high conversion mostly in the ring to afford predominantly 4-bromo-3,3,6,6-tetrafluoro-1,4-cyclohexadienecarboxamide. 4-Bromonitrobenzene in a low yield gave 4-bromofluoronitrobenzene and 3,4-dibromofluoronitrobenzene. 3-Bromo-nitrobenzene and 1,4-dichlorobenzene did not undergo fluorination. In the course of the electrolysis of the 4-bromobenzamide and 4-bromonitrobenzene in anhydrous HF apart the fluorination occurred also the bromination of the substrates. Pleiades Publishing, Inc. 2006.
Benzooxazole and benzothiazole antagonists of gonadotropin releasing hormone receptor
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Page/Page column 30; 41, (2008/06/13)
The present invention relates to Gonadotropin Releasing Hormone (GnRH, also known as Luteinizing Hormone Releasing Hormone) receptor antagonists.
Lysine-enediyne conjugates as photochemically triggered DNA double-strand cleavage agents
Kovalenko, Serguei V.,Alabugin, Igor V.
, p. 1444 - 1446 (2007/10/03)
Statistical analysis of DNA-photocleavage by two types of lysine-enediyne conjugates confirms that more double-strand breaks are produced than can be accounted for by coincident single-strand breaks. The Royal Society of Chemistry 2005.
Aromatic allylation via diazotization: Metal-free C-C bond formation
Ek, Fredrik,Axelsson, Oskar,Wistrand, Lars-Goeran,Frejd, Torbjoern
, p. 6376 - 6381 (2007/10/03)
A new method for the synthesis of allyl aromatic compounds not involving any metal-containing reagent or catalyst has been developed. Arylamines substituted with a large number of different substituents were converted via diazotizative deamination with tert-butyl nitrite in allyl bromide and acetonitrile to the corresponding allyl aromatic compounds. The allylation reaction was found to be suitable for larger scale synthesis due to short reaction times, a nonextractive workup, and robustness toward moisture, air, and type of solvent.