- Synthesis of quinolinones with palladium-catalyzed oxidative annulation between acrylamides and arynes
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An unprecedented palladium-catalyzed oxidative annulation of acrylamides with benzyne precursors has been successfully developed. By using this mild "N-H activation/Heck reaction" method, a wide variety of quinolinones were conveniently prepared in one st
- Wang, Weiguo,Peng, Xianglong,Qin, Xiaoyu,Zhao, Xiangyun,Ma, Chen,Tung, Chen-Ho,Xu, Zhenghu
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- Visible-Light Mediated Metal-Free 6π-Photocyclization of N-Acrylamides: Thioxanthone Triplet Energy Transfer Enables the Synthesis of 3,4-Dihydroquinolin-2-ones
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An efficient thioxanthone-catalyzed triplet energy transfer process for the synthesis of 3,4-dihydroquinolin-2-ones via a 6π-photocyclization is reported. Featuring a rare example of a metal-free formal C(sp2)-H/C(sp3)-H arylation mediated by visible-ligh
- Oddy, Meghan J.,Kusza, Daniel A.,Petersen, Wade F.
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p. 8963 - 8967
(2021/11/24)
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- Nickel-Catalyzed Intramolecular Arylcyanation for the Synthesis of 3,3-Disubstituted Oxindoles
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A nickel-catalyzed arylcyanation reaction for the synthesis of 3,3-disubstituted oxindoles has been developed. This method features a bench-stable precatalyst system and serves as an economical alternative to the existing palladium-catalyzed arylcyanations described to date. A wide scope of oxindole products were accessible in moderate to good yields, and the rich chemistry of the newly installed nitrile functional group was demonstrated in the synthesis of various oxindole derivatives.
- Yen, Andy,Lautens, Mark
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p. 4323 - 4327
(2018/07/29)
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- An organocatalyst bound α-aminoalkyl radical intermediate for controlled aerobic oxidation of iminium ions
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A catalyst bound α-aminoalkyl radical intermediate from iminium is developed to control its formation and reactivity with aerobic oxygen. The influence of the catalyst was demonstrated via the ease of radical intermediate formation and its subsequent reactivity, including the first catalyst-controlled enantioselective aerobic oxidation with a chiral phosphite catalyst.
- Motaleb, Abdul,Bera, Asish,Maity, Pradip
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p. 5081 - 5085
(2018/07/29)
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- Transition-Metal-Free Direct C-H Arylation of Quinoxalin-2(1H)-ones with Diaryliodonium Salts at Room Temperature
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A method of synthesizing 3-arylquinoxalin-2(1H)-ones using diaryliodonium tetrafluoroborates under mild conditions is described. This protocol has a wide substrate scope and enables direct C-H functionalization. The synthetic potential of this coupling was explored using a range of readily accessible diaryliodonium salts and quinoxalin-2(1H)-ones.
- Yin, Kun,Zhang, Ronghua
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supporting information
p. 1530 - 1533
(2017/04/13)
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- Metal-Free Synthesis of 3-Arylquinolin-2-ones from N,2-Diaryl- acrylamides via Phenyliodine(III) Bis(2,2-dimethylpropanoate)- Mediated Direct Oxidative C?C Bond Formation
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Treatment of N,2-diarylacrylamides with the organoiodine(III) compound phenyliodine(III) bis(2,2-dimethylpropanoate) [PhI(O2C-t-Bu)2] and boron trifluoride etherate (BF3?Et2O) resulted in a direct and selective oxidative C(sp2)?C(sp2) bond formation leading to a convenient assemblage, under mild conditions, of the biologically important 3-arylquinolin-2-one skeleton. Differing from the five-membered oxindole products from oxidative cyclizations mediated by transition metals, this metal-free approach realized a direct annulation of the N-arylacrylamide into a six-membered 3-arylquinolin-2-one skeleton. (Figure presented.).
- Cao, Yang,Zhao, Hui,Zhang-Negrerie, Daisy,Du, Yunfei,Zhao, Kang
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p. 3610 - 3615
(2016/11/25)
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- KMnO4/AcOH-mediated C3-selective direct arylation of coumarins with arylboronic acids
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An efficient protocol for KMnO4/AcOH-mediated dehydrogenative direct radical arylation of coumarins with arylboronic acids to afford 3-arylcoumarin derivatives is described. A similar reaction system is also applicable to the 3-arylation of quinolinone derivatives. These KMnO4/AcOH-mediated coupling reactions occur regioselectively at the C3 position of coumarins and quinolinones. Some notable features of this method are high efficiency, moderate to good yield, and a broad group tolerance.
- Yuan, Jin-Wei,Yang, Liang-Ru,Yin, Qiu-Yue,Mao, Pu,Qu, Ling-Bo
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p. 35936 - 35944
(2016/05/19)
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- Metal-Free Synthesis of 3-Arylquinolin-2-ones from Acrylic Amides via a Highly Regioselective 1,2-Aryl Migration: An Experimental and Computational Study
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Combined experimental and theoretical investigations into the phenyliodine bis(trifluoroacetate) (PIFA)-mediated reaction of N-arylcinnamamide to produce 3-arylquinolin-2-one derivatives have been conducted. High regioselectivity during the aryl migration process was observed in 3,3-disubstituted acrylamides. Density functional theory calculation was conducted in an attempt to understand the mechanism and the origin of the regioselectivity. On the basis of both the experimental and the theoretical results, a mechanism involving an oxidative annulation, followed by an aryl migration, has been proposed. The annulation is the regioselectivity determining step.
- Liu, Le,Zhang, Tonghuan,Yang, Yun-Fang,Zhang-Negrerie, Daisy,Zhang, Xinhao,Du, Yunfei,Wu, Yun-Dong,Zhao, Kang
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p. 4058 - 4065
(2016/06/08)
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- Metal-free ring expansion of indoles with nitroalkenes: A simple, modular approach to 3-substituted 2-quinolones
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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
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p. 8647 - 8656
(2015/03/03)
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- Manganese-mediated C3-selective direct alkylation and arylation of 2-pyridones with diethyl malonates and arylboronic acids
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A manganese-mediated dehydrogenative direct alkylation of 2-pyridones with diethyl malonates has been developed. A similar reaction system is applicable to the direct arylation with arylboronic acids. These manganese-based reactions occur regioselectively at the C3 position of the 2-pyridones. The observed high C3 regioselectivity can complement precedented C-H functionalization protocols of the 2-pyridones in view of the site selectivity.
- Nakatani, Akihiro,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
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p. 1377 - 1385
(2014/03/21)
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- Metal-free transannulation reaction of indoles with nitrostyrenes: A simple practical synthesis of 3-substituted 2-quinolones
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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
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supporting information
p. 9305 - 9307
(2013/10/01)
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- PhI(OCOCF3)2-mediated C-C bond formation concomitant with a 1,2-Aryl shift in a metal-free synthesis of 3-arylquinolin-2-ones
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The reaction of the readily available N-methyl-N-phenylcinnamamides with phenyliodine bis(trifluoroacetate) (PIFA) in the presence of Lewis acids provides a general and efficient assembly of a variety of 3-arylquinolin-2-one compounds. This novel approach features not only metal-free oxidative C(sp 2)-C(sp2) bond formation but also an exclusive 1,2-aryl migration.
- Liu, Le,Lu, Hang,Wang, Hong,Yang, Chao,Zhang, Xiang,Zhang-Negrerie, Daisy,Du, Yunfei,Zhao, Kang
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p. 2906 - 2909
(2013/07/26)
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- Palladium-catalyzed decarboxylative coupling of quinolinone-3-carboxylic acids and related heterocyclic carboxylic acids with (Hetero)aryl halides
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An efficient and practical decarboxylative cross-coupling reaction of quinolin-4(1H)-one 3-carboxylic acids with (hetero)aryl halides has been established. Under a bimetallic system of PdBr2 and silver carbonate, the protocol proved to be general, and a variety of 3-(hetero)aryl 4-quinolinones and related heterocycles, such as 3-aryl-1,8-naphthyridin-4(1H)- ones, 3-arylcoumarins, 3-arylquinolin-2(1H)-ones, and 2-arylchromones, can be prepared in good to excellent yields.
- Messaoudi, Samir,Brion, Jean-Daniel,Alami, Mouad
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supporting information; experimental part
p. 1496 - 1499
(2012/05/20)
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- Facile synthesis of 3-substituted and 1,3-disubstituted quinolin-2(1H)-ones from 2-nitrobenzaldehydes
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2-Nitrobenzaldehydes were reduced with iron powder to 2-aminobenzaldehydes, which were reacted immediately with acyl chlorides to provide 2-carboxamidobenzaldehydes (1) with overall yields of 71-90 %. Reaction of 1 with base provided 3-substituted quinolin-2(1H)-ones with 63-97 % yields. Treatment of 1 with methyl iodide and base gave 1-methyl-3-substituted quinolin-2(1H)-ones with 82-95 % yields, whereas the treatment with isopropyl iodide gave 1-isopropyl-3-substituted quinolin-2(1H)-ones with 7-42 % yields.
- Park, Kwanghee Koh,Jung, Jin Young
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p. 2095 - 2105
(2007/10/03)
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- A new synthesis of naphthyridinones and quinolinones: Palladium-catalyzed amidation of o-carbonyl-substituted aryl halides
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(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.
- Manley, Peter J.,Bilodeau, Mark T.
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p. 2433 - 2435
(2007/10/03)
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- Rhodium-catalyzed carbonylation of 2-alkynylaniline: Syntheses of 1,3-dihydroindol-2-ones
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Rhodium-catalyzed carbonylation of 2-alkynylanilines under water-gas shift reaction conditions gives 3-alkyl-1,3-dihydroindol-2-ones 2 in good yields along with a small amount of 2-quinolone derivatives 4. The reaction under carbonylation conditions witho
- Hirao, Kojiro,Morii, Noritsugu,Joh, Takashi,Takahashi, Shigetoshi
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p. 6243 - 6246
(2007/10/02)
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