83010-83-7Relevant academic research and scientific papers
Use of a readily removable auxiliary group for the synthesis of pyrrolidones by the palladium-catalyzed intramolecular amination of unactivated γ C(sp3)-H Bonds
He, Gang,Zhang, Shu-Yu,Nack, William A.,Li, Qiong,Chen, Gong
supporting information, p. 11124 - 11128 (2013/10/22)
Easy on, easy off: Directing groups found to promote the palladium-catalyzed amination of γ C(sp3)-H and C(sp 2)-H bonds of secondary amides included 5-methoxy-8-aminoquinoline, which can be removed under mild conditions (see scheme; CAN=ceric ammonium nitrate). In conjunction with a β-C-H methylation or γ-C-H arylation step, the γ-C(sp3)-H amination provided access to complex pyrrolidones from readily available precursors. Copyright
Novel Sulfonaminoquinoline Hepcidin Antagonists
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Page/Page column 130, (2012/09/05)
The present invention relates to novel hepcidin antagonists, pharmaceutical compositions comprising them and the use thereof as medicaments for the use in the treatment of iron metabolism disorders, such as, in particular, iron deficiency diseases and anemias, in particular anemias in connection with chronic inflammatory diseases.
Direct methoxylation of nitroarenes and nitroazaarenes with alkaline methoxides via nucleophilic displacement of an aromatic hydrogen atom
Kawakami, Takehiko,Suzuki, Hitomi
, p. 1259 - 1264 (2007/10/03)
Treatment of 1,3-dinitrobenzene and 5-substituted derivatives with excess potassium or sodium methoxide in 1,3-dimethylimidazolidin-2-one (DMI) at room temperature results in the displacement of an aromatic hydrogen at the 4-position by methoxide, affording 2,4-dinitroanisole and its 6-substituted derivatives, respectively, in low to moderate yield. In contrast, an equimolar reaction under similar conditions leads to the replacement of the nitro group in preference to the ring hydrogen. The reaction does not take place with lithium methoxide as a base. Mono- and dinitronaphthalenes and nitroquinolines undergo similar displacement of a hydrogen atom at the position ortho or para to the nitro group, giving the corresponding methoxy derivatives in moderate yield. A slow addition of the nitro compound to a large excess of potassium methoxide under an oxygen atmosphere has been found to enhance the conversion and improve the product yield. On the basis of the product distribution as well as the kinetic isotope effect kH/kD = 2.1, direct displacement of a ring hydrogen atom by methoxide ion has been interpreted in terms of the rate-determining release of an ipso-hydrogen atom as a proton from the initially formed Meisenheimer adduct.
THE SYNTHESIS OF THREE ISOMERS OF THE FOOD CARCINOGEN IQ
Ronne, Erik,Grivas, Spiros
, p. 101 - 105 (2007/10/02)
2-Amino-3-methyl-3H-imidazoquinoline, 2-amino-3-methyl-3H-imidazoisoquinoline and 2-amino-3-methyl-3H-imidazoisoquinoline were synthesized from 7-methoxyquinoline, 6- and 7-methoxyisoquinolines in 21-28percent overall yields.
Oxidative Methylamination of Nitroquinolines
Wozniak, Marian,Grzegozek, Maria
, p. 823 - 830 (2007/10/02)
3-, 5-, 6-, 7- and 8-nitroquinoline as well as 5,7- and 6,8-dinitroquinoline are methylaminated with a liquid methylamine solution of potassium permanganate (LMA/PP) to the corresponding mono- and bis(methylamino)-substituted compounds. 2-Nitroquinoline is aminated with LMA/PP to 2-(methylamino)quinoline.The intermediate methylamino ?-adducts of 3-nitro- and 5,7- and 6,8-dinitroquinoline are detected by 1H-NMR spectroscopy.Quantum chemical calculations for the mononitroquinolines suggest that the experimentally observed regioselectivity of the methylamination is controlled by an interaction of frontal molecular orbitals (FMO) of the reagents. Key Words: Methylaminations / ?-Adducts, methylamino / Calculations, FMO / Quinolines / Aminations
