55164-80-2Relevant academic research and scientific papers
Palladium-catalyzed carbonylative synthesis of 3-arylquinolin-2(1H)-ones from benzyl chlorides and o-nitrobenzaldehydes
Hou, Chen-Yang,Liu, Jian-Li,Qi, Xinxin,Wu, Xiao-Feng
, (2021/09/02)
A palladium-catalyzed carbonylative cyclization of benzyl chlorides with o-nitrobenzaldehydes has been developed for the synthesis of 3-arylquinolin-2(1H)-ones. Mo(CO)6 played a dual role as both a CO surrogate and a reductant in this carbonylative transformation.
Palladium-Catalyzed Reductive Aminocarbonylation of Benzylammonium Triflates with o-Nitrobenzaldehydes for the Synthesis of 3-Arylquinolin-2(1 H)-ones
Liu, Yongzhu,Qi, Xinxin,Wu, Xiao-Feng
, p. 13824 - 13832 (2021/10/12)
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.
Preparation method of 3-aryl quinoline-2 (1H) ketone derivative
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Paragraph 0032-0040, (2021/07/01)
The invention discloses a preparation method of a 3-aryl quinoline-2 (1H) ketone derivative. The method comprises the following steps: carrying out a reaction on palladium acetate, S)-1, 1'-binaphthyl-2, 2'-diphenylphosphine, carbonyl molybdenum, triethylamine, water, benzisoxazole and a benzyl chloride compound at 100 DEG C for 26 hours, and after the reaction is completed, carrying out post-treatment to obtain the 3-aryl quinoline-2 (1H) ketone derivative. According to the preparation method, benzisoxazole is used as a nitrogen source and a formyl source, the operation is simple, the reaction initial raw materials are cheap and easy to obtain, the tolerance range of substrate functional groups is wide, and the reaction efficiency is high; and various 3-aryl quinoline-2 (1H) ketone derivatives can be synthesized according to actual needs, and the practicability of the method is widened while the operation is convenient.
Supported Palladium Nanoparticles-Catalyzed Synthesis of 3-Substituted 2-Quinolones from 2-Iodoanilines and Alkynes Using Oxalic Acid as C1 Source
Thakur, Vandna,Sharma, Ajay,Yamini,Sharma, Nishtha,Das, Pralay
supporting information, p. 426 - 431 (2018/12/13)
3-Aryl/alkyl-2-quinolones were synthesized employing microwave assisted multicomponent reaction of 2-iodoanilines, terminal alkynes and oxalic acid dihydrate ((CO2H)2 ? 2H2O) under polystyrene supported palladium (Pd@PS) nanoparticles-catalyzed conditions. The use of a heterogeneous palladium catalyst was explored first time for 2-quinolone synthesis involving carbonylation reaction employing (CO2H)2 ? 2H2O as a solid and bench stable carbon monoxide (CO) source. The reaction exhibited good substrate generality for 2-iodoanilines and alkynes with wide functional group tolerance and good regio-selectivity. The ligand free operation, recyclability of heterogeneous Pd@PS catalyst and use of bench stable C1 source are the invaluable merits of the protocol. (Figure presented.).
Synthesis of 3-substituted quinolin-2(1H)-ones via the cyclization of o-alkynylisocyanobenzenes
Charoenpol, Ailada,Meesin, Jatuporn,Khaikate, Onnicha,Reutrakul, Vichai,Pohmakotr, Manat,Leowanawat, Pawaret,Soorukram, Darunee,Kuhakarn, Chutima
, p. 7050 - 7054 (2018/10/17)
A facile synthesis of various functionalized 3-substituted quinolin-2(1H)-ones through Ag(i) nitrate-catalyzed cyclization of o-alkynylisocyanobenzenes is described. The reaction allows rapid and convenient access to 3-substituted quinolin-2(1H)-one scaffolds in moderate to good yields.
Metal-free ring expansion of indoles with nitroalkenes: A simple, modular approach to 3-substituted 2-quinolones
Aksenov, Alexander V.,Smirnov, Alexander N.,Aksenov, Nicolai A.,Aksenova, Inna V.,Matheny, Jonathon P.,Rubin, Michael
, p. 8647 - 8656 (2015/03/03)
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.
Highly efficient modular metal-free synthesis of 3-substituted 2-quinolones
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)
A modular approach to 3-substituted 2-quinolones via a cascade annulation reaction between 4-nitroketones and hydrazines has been developed.
Metal-free transannulation reaction of indoles with nitrostyrenes: A simple practical synthesis of 3-substituted 2-quinolones
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)
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.
Intramolecular amidation - An efficient synthesis of 3-aryl-2-quinolinones
Luo, Yinggang,Tao, Feiyan,Liu, Yan,Li, Bogang,Zhang, Guolin
, p. 1620 - 1625 (2007/10/03)
To reveal the scope of the syntheses of 3-aryl-2-quinolinones from 2-nitro-α-phenylcinnamic acids, the isomerization of (E)-2-amino-α- phenylcinnamic acids was studied. The results showed that (E)-2-amino-α- phenylcinnamic acids were isomerized to its (Z)
A new synthesis of naphthyridinones and quinolinones: Palladium-catalyzed amidation of o-carbonyl-substituted aryl halides
Manley, Peter J.,Bilodeau, Mark T.
, p. 2433 - 2435 (2007/10/03)
(Equation Presented) An alternative to the Friedlander condensation for the synthesis of naphthyridinones and quinolinones has been discovered. Palladium-catalyzed amidation of halo aromatics substituted in the ortho position by a carbonyl functional group or its equivalent with primary or secondary amides leads to the formation of substituted naphthyridinones and quinolinones.
