363-47-3Relevant articles and documents
AMINATION AND HYDROXYLATION OF ARYLMETAL COMPOUNDS
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Paragraph 0098; 0134; 0135; 0186, (2018/03/25)
In one aspect, the present disclosure provides methods of preparing a primary or secondary amine and hydroxylated aromatic compounds. In some embodiments, the aromatic compound may be unsubstituted, substituted, or contain one or more heteroatoms within the rings of the aromatic compound. The methods described herein may be carried out without the need for transition metal catalysts or harsh reaction conditions.
Rapid heteroatom transfer to arylmetals utilizing multifunctional reagent scaffolds
Gao, Hongyin,Zhou, Zhe,Kwon, Doo-Hyun,Coombs, James,Jones, Steven,Behnke, Nicole Erin,Ess, Daniel H.,Kürti, László
, p. 681 - 688 (2017/06/30)
Arylmetals are highly valuable carbon nucleophiles that are readily and inexpensively prepared from aryl halides or arenes and widely used on both laboratory and industrial scales to react directly with a wide range of electrophiles. Although C-C bond formation has been a staple of organic synthesis, the direct transfer of primary amino (-NH2) and hydroxyl (-OH) groups to arylmetals in a scalable and environmentally friendly fashion remains a formidable synthetic challenge because of the absence of suitable heteroatom-transfer reagents. Here, we demonstrate the use of bench-stable N-H and N-alkyl oxaziridines derived from readily available terpenoid scaffolds as efficient multifunctional reagents for the direct primary amination and hydroxylation of structurally diverse aryl- and heteroarylmetals. This practical and scalable method provides one-step synthetic access to primary anilines and phenols at low temperature and avoids the use of transition-metal catalysts, ligands and additives, nitrogen-protecting groups, excess reagents and harsh workup conditions.
NOVEL FLUORESCENT DYES AND USES THEREOF
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Page/Page column 32-33, (2011/02/24)
The present invention provides fluorescent dyes that are based on firefly luciferin structure. These dyes are optimally excited at shorter wavelengths and have Stokes shift of at least 50 nm. The fluorescent dyes of the invention are useful for preparation of dye-conjugates, which can be used in detection of an analyte in a sample.
PYRIDIN-4-YL-ETHYNYL-IMIDAZOLES AND PYRAZOLES AS MGLU5 RECEPTOR ANTAGONISTS
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Page/Page column 40, (2008/06/13)
The present invention relates to diazole derivatives of the general formula (I) wherein A, E, R1, Wand R3 are as defined in the claims and description, their use for the preparation of medicaments for treating diseases and processes
Synthesis of COX-2 and FAAH inhibitors
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, (2008/06/13)
Methods for preparing indoles that are useful COX-2 inhibitors and intermediates useful in such methods are described.
Electrophilic aromatic fluorination with fluorine: meta-Directed fluorination of anilines
Alric,Marquet,Billard,Langlois
, p. 661 - 667 (2007/10/03)
Anilines are mainly or selectively fluorinated in the meta-position with F2 when dissolved in triflic acid, sometimes in the presence of small quantities of antimony pentafluoride. The regioselectivity is increased when an electron-donating substituent is present at the para-position.
2,6-difluorophenol as a bioisostere of a carboxylic acid: Bioisosteric analogues of γ-aminobutyric acid
Qiu, Jian,Stevenson, Scott H.,O'Beirne, Michael J.,Silverman, Richard B.
, p. 329 - 332 (2007/10/03)
3-(Aminomethyl)-2,6-difluorophenol (6) and 4-(aminomethyl)-2,6- difluorophenol (7) were synthesized in eight and four steps, respectively, starting from 2,6-difluorophenol, to test the potential of the 2,6- difluorophenol moiety to act as a lipophilic bio
The effect of fluorine substitution on the physicochemical properties and the analgesic activity of paracetamol
Barnard,Storr,O'Neill,Park
, p. 736 - 744 (2007/10/02)
The physicochemical properties and analgesic action of six fluorinated analogues of 4-hydroxyacetanilide (paracetamol) have been investigated. Fluorine substitution adjacent to the hydroxyl group increased lipophilicity and oxidation potential whilst substitution adjacent to the amide had little effect on lipophilicity but led to a greater increase in oxidation potential. Lack of coplanarity and conjugation of the amide group and aromatic ring was also apparent with the analogues that had fluorine in the 2 and 6 positions. Introduction of fluorine into the amide group of paracetamol increased the lipophilicity 4-fold and also increased the oxidation potential of paracetamol. ED50 values for analgesic activity in the phenylquinone-induced abdominal constriction test on male Swiss White mice showed that ring substitution by fluorine reduced activity, especially at the 2,6-positions. Introduction of fluorine into the amide group enhanced activity significantly. Correlation of the analgesic activity with the physicochemical properties indicated that conjugation (and planarity) of the amide group with the aromatic ring is essential for activity and that ease of oxidation may also be an important factor.