25871-25-4Relevant academic research and scientific papers
Nickel-catalyzed electrochemical Minisci acylation of aromatic N-heterocycles with α-keto acids via ligand-to-metal electron transfer pathway
Ding, Hang,Xu, Kun,Zeng, Cheng-Chu
, p. 38 - 43 (2020)
A nickel-catalyzed electrochemical methodology for the Minisci acylation of aromatic electron-deficient heterocycles with α-keto acids has been developed. The reaction is performed in an undivided cell under constant current conditions, featuring broad scope of substrates and avoiding the conventional utilization of silver-based catalysts in conjunction with excess amount of oxidants. Cyclic voltammetric analysis disclosed that a ligand-to-metal electron transfer process may be involved in the generation of the key acyl radicals.
Oxidant-Controlled C-sp2/sp3-H Cross-Dehydrogenative Coupling of N-Heterocycles with Benzylamines
Sharma, Rohit,Abdullaha, Mohd,Bharate, Sandip B.
, p. 9786 - 9793 (2017/09/23)
Oxidant controlled ionic liquid mediated cross-dehydrogenative coupling (CDC) of benzylamines with N-heterocycles having sp2 or sp3 carbon resulted in the formation of C-benzoylated or alkenylated products. Benzoylation of N-heterocycles occurs via (NH4)2S2O8 catalyzed benzoyl radical formation. An oxidative alkenylation of N-heterocycles having C-sp3 carbon (2-methylaza-arenes) occurs via deamination of benzylamine followed by C-sp3-H bond activation in high stereoselectivity. Both benzoylation and alkenylation protocols are metal-free, green, simple, efficient, and tolerate a wide variety of functional groups.
Regiospecific benzoylation of electron-deficient n -heterocycles with methylbenzenes via a minisci-type reaction
Ali, Wajid,Behera, Ahalya,Guin, Srimanta,Patel, Bhisma K.
, p. 5625 - 5632 (2015/06/16)
A regioselective cross-dehydrogenative coupling between electron-deficient N-heterocycles (isoquinoline, quinolines, and quinoxalines) and methylbenzenes leading to regiospecific C-aroylation has been accomplished using AlCl3 as the catalyst in
Synthesis of 2-aroylquinoxalines, 1-aroylphthalazines, and 4-aroylcinnolines; an aroylation method using arenecarbaldehydes catalyzed by azolium salt1
Miyashita, Akira,Suzuki, Yumiko,Iwamoto, Ken-Ichi,Oishi, Etsuo,Higashino, Takeo
, p. 405 - 413 (2007/10/03)
2-Aroylquinoxalines (5,6), 1-aroylphthalazines (10,11), and 4-aroylcinnolines (13) were synthesized by using arenecarbaldehydes (2) in the presence of an azolium salt (1) in moderate to good yields. 1,3-Dimethylimidazolium iodide (1a) and sodium sulfinate
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
