42606-39-3Relevant academic research and scientific papers
Synthesis and Antiproliferative Activity of Some Ellipticine-Like 11H-Pyrido[a]carbazole Derivatives
Ferlin, Maria Grazia,Gia, Ornella,DallaVia, Lisa
experimental part, p. 1872 - 1883 (2012/07/03)
Some modified 11H-pyrido[a]carbazoles (11H-PyC) and their corresponding tetrahydro derivatives (11H-THPyC) were prepared. A common multistep pathway characterized by conventional reactions, including a Fischer-indole-type synthesis, yielded the tetracycli
Vicarious nucleophilic amination of nitroquinolines by 1,1,1- trimethylhydrazinium iodide
Grzegozek, Maria
experimental part, p. 1879 - 1882 (2009/06/18)
(Chemical Equation Presented) The amination of 3-, 5-, 6-, 7- and 8-nitroquinoline via the vicarious nucleophilic substitution of hydrogen (VNS) with 1,1,1-trimethylhydrazinium iodide (TMHI) in the presence of t-BuOK in DMSO was studied. The amination occurs regioselectively giving ortho or ortho and para isomers relative to the nitro group with a high yield (95-86%). 2-Nitroquinoline does not undergo vicarious amination but displacement of the labile nitro group by an amino group occurs and then transformation to an imine compound and hydrolysis gives 2(1H)-quinolinone.
Vicarious nucleophilic amination of Nitroquinolines with 4-amino-1,2,4-triazole
Szpakiewicz, Barbara,Grzegozek, Maria
, p. 682 - 685 (2008/09/21)
3-, 5-. 6-, 7- and 8-Nitroquinolines react with 4-amino-l,2,4-triazole in basic medium (potassium tert-butoxide-dimethyl sulfoxide) giving amino products of the vicarious nucleophilic substitution (VNS) of hydrogen, predominantly at ortho position to the nitro group, except 8-nitroquinoline, which reacts at para position. Additionally, furazano[3,4-f]- and furazano[3,4-zh]quinoline were obtained in the case of 5- and 8- nitroquinoline, respectively. 2-Nitroquinoline was aminated to 2-quinolino(l,2,4-triazol-4-yl)amine in these conditions.
Quinone imines with a fused azine ring: III. Synthesis and reactivity of 8-p-tolylsulfonylimino-5,8-dihydroquinolin-5-one derivatives
Belov,Nichvoloda
, p. 124 - 127 (2007/10/03)
Unstable 8-p-tolylsulfonylimino-5,8-dihydroquinolin-5-one was generated by oxidation of the corresponding reduced form in acetic acid; it reacted in situ with hydrogen chloride and sodium p-toluenesulfinate to give the corresponding 6-substituted 5-hydrox
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
