105702-33-8Relevant articles and documents
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
