Palladium-Catalyzed Reductive Aminocarbonylation of Benzylammonium Triflates with o-Nitrobenzaldehydes for the Synthesis of 3-Arylquinolin-2(1 H)-ones
A palladium-catalyzed straightforward procedure for the synthesis of 3-arylquinolin-2(1H)-ones has been developed. The synthesis proceeds through a palladium-catalyzed reductive aminocarbonylation reaction of benzylic ammonium triflates with o-nitrobenzaldehydes, and a wide range of 3-arylquinolin-2(1H)-ones was obtained in moderate to good yields with very good functional group compatibility.
Liu, Yongzhu,Qi, Xinxin,Wu, Xiao-Feng
p. 13824 - 13832
(2021/10/12)
Metal-free ring expansion of indoles with nitroalkenes: A simple, modular approach to 3-substituted 2-quinolones
3-Substituted 2-quinolones are obtained via a novel metal-free transannulation reaction of 2-nitroolefins with 2-substituted indoles in polyphosphoric acid. This acid-mediated cascade transformation operates via the ANRORC (Addition of Nucleophile, Ring Opening, and Ring Closure) mechanism and can be used in combination with the Fisher indole synthesis to offer a practical three-component hetero-annulation approach to 2-quinolones from arylhydrazines, 2-nitroalkenes, and acetophenone. An alternative entry to this chemistry employing the alkylation of electron-rich arenes and hetarenes with 1-(2-indolyl)-2-nitroalkene has also been demonstrated.
Aksenov, Alexander V.,Smirnov, Alexander N.,Aksenov, Nicolai A.,Aksenova, Inna V.,Matheny, Jonathon P.,Rubin, Michael
p. 8647 - 8656
(2015/03/03)
Highly efficient modular metal-free synthesis of 3-substituted 2-quinolones
A modular approach to 3-substituted 2-quinolones via a cascade annulation reaction between 4-nitroketones and hydrazines has been developed.
Aksenov, Alexander V.,Smirnov, Alexander N.,Aksenov, Nicolai A.,Aksenova, Inna V.,Bijieva, Asiyat S.,Rubin, Michael
supporting information
p. 9786 - 9788
(2014/12/12)
Metal-free transannulation reaction of indoles with nitrostyrenes: A simple practical synthesis of 3-substituted 2-quinolones
3-Substituted 2-quinolones are obtained via a novel, metal-free transannulation reaction of 2-substituted indoles with 2-nitroalkenes in polyphosphoric acid. The reaction can be used in conjunction with the Fisher indole synthesis offering a practical three-component heteroannulation methodology to produce 2-quinolones from arylhydrazines, 2-nitroalkenes and acetophenone.
Aksenov, Alexander V.,Smirnov, Alexander N.,Aksenov, Nicolai A.,Aksenova, Inna V.,Frolova, Liliya V.,Kornienko, Alexander,Magedov, Igor V.,Rubin, Michael
supporting information
p. 9305 - 9307
(2013/10/01)
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