105702-41-8Relevant academic research and scientific papers
Heteroannulation through copper catalysis: A novel cyclisation leading to an unusual formation of 2-aroylquinoxalines
Mukhopadhyay,Kundu
, p. 9927 - 9930 (2000)
N-[(3'-Aryl)prop-2'-ynyl]-N,N'-1,2-phenylene di-p-tosylamides, 15-22, underwent an unusual ring closure with potassium carbonate (2 equiv.) and copper(I) iodide (10 mol%) in DMF at 100°C for 24 h to yield 2-aroylquinoxalines (23-30) instead of the expecte
Bifunctional Oxo-Tethered Ruthenium Complex Catalyzed Asymmetric Transfer Hydrogenation of Aryl N-Heteroaryl Ketones
Wang, Baigui,Zhou, Haifeng,Lu, Guoren,Liu, Qixing,Jiang, Xiaolan
supporting information, p. 2094 - 2097 (2017/04/28)
A facile asymmetric transfer hydrogenation of ortho-substituted aryl N-heteroaryl ketones and non-ortho-substituted N-oxide of aryl N-heteroaryl ketones using a readily available oxo-tethered ruthenium complex as a catalyst and sodium formate as a hydrogen source in an aqueous solution has been discovered. A variety of chiral aryl N-heteroaryl methanols were obtained with up to 99.9% ee.
A new facile, efficient synthesis and structure peculiarity of quinoxaline derivatives with two benzimidazole fragments
Mamedov, Vakhid A.,Zhukova, Nataliya A.,Syakaev, Victor V.,Gubaidullin, Aidar T.,Beschastnova, Tat'Yana N.,Adgamova, Dil'Bar I.,Samigullina, Aida I.,Latypov, Shamil K.
, p. 1403 - 1416 (2013/02/23)
A highly efficient and versatile method for the synthesis of quinoxaline derivatives with two benzimidazole fragments have been developed on the basis of the ring contraction of 3-(benzimidazo-2-yl)quinoxalin-2(1H)-one with 1,2-diaminobenzene and its various types of substituted and condensed derivatives. Owing to the inter- and intramolecular processes, involving self association, proton exchange, conformational, and/or tautomeric exchanges between several forms for most of the bis-benzimidazolylquinoxalines signals of bridged and neighboring carbon atoms and the hydrogen atoms of the neighboring carbon atoms of benzimidazole fragments in the NMR spectra are broadened. The conjugation between the benzimidazole fragments and the quinoxaline core of the molecules is increased from the quinoxaline derivative (10c) to its thiadiazol[f]- (17) and pyrrolo[a]-(19) annulated derivatives, resulting in a greater planarity of the molecule as a whole.
Quinoxalines. XXII. Aryl Migration of 2-Aroylquinoxalines to 2-Arylquinoxalines
Higashino, Takeo,Takemoto, Masumi,Tanji, Ken-Ichi,Iijima, Chihoko,Hayashi, Eisaku
, p. 4193 - 4201 (2007/10/02)
The reaction of 2-aroylquinoxalines (1) with sodium hydroxide in dimethyl sulfoxide (DMSO) was found to result in aryl migration, fission of the C2-C=O bond, and addition of DMSO to the C=O group, giving 2-arylquinoxalines (2), quinoxaline (4), aroic acids (5), and α-aryl-α-(methylsulfinylmethyl)-2-quinoxalinemethanols (6).Compounds 6 could be separatedinto two racemates, (αR*,SR*)-6, and (αR*,SS*)-6.In order to establish the generality of the aryl migration, other aroylated aromatic heterocycles were examined. 3-Aroylpyridopyrazines (7) and 1-benzoyl-4-isoquinolinecarbonitrile (10) both underwent similar aryl migration to give 3-arylpyridopyrazines (14) and 1-phenyl-4-isoguinolinecarbonitrile (18), respectively.On the other hand, the reaction of 1-benzoylisoquinoline (9) and 2-benzoilquinoline (11) resulted not in migration, but in the addition of DMSO to give 1-isoquinolinemethanol (16) and 2-quinolinemethanol derivatives (20), respectively.In the case of 1-benzoylphtalazine (8), migration did not occur, but instead 4-benzoyl-1(2H)-phthalazinone (15) was formed.Keywords - 2-aroylquinoxaline; 2-arylquinoxaline; 2-quinoxalinemethanol; aryl migration; racemate; 3-arylpyridopyrazine; 1-isoquinolinemethanol; 2-quinolinemethanol; 1-phenyl-4-isoquinolinecarbonitrile; 4-benzoyl-1(2H)-phthalazinone
