- Metal-Free C-H [5 + 1] Carbonylation of 2-Alkenyl/Pyrrolylanilines Using Dioxazolones as Carbonylating Reagents
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A novel metal-free C-H [5 + 1] carbonylative annulation of 2-alkenyl/pyrrolylanilines with dioxazolones has been established for the assembly of the privileged quinolinones and pyrrolyl-fused quinoxalinones. Entirely differing from the existing reports, the dioxazolones herein behave with an innovative chemistry and first emerge as carbonylating reagents to participate in annulation reactions. Moreover, this process features exceedingly simple operation (only solvent) and tolerates both vinyl and aryl substrates. Comprehensive mechanistic studies indicate that the formed isocyanate intermediate plays a crucial role in enabling the carbonylation annulation.
- Nan, Jiang,Chen, Pu,Gong, Xue,Hu, Yan,Ma, Qiong,Wang, Bo,Ma, Yangmin
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supporting information
p. 3761 - 3766
(2021/05/10)
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- 1,4,2-Dioxazol-5-ones as Isocyanate Equivalents: An Efficient Synthesis of 2-Quinolinones via β-Keto Amides
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Under thermal conditions, 1,4,2-dioxazol-5-ones are known to undergo decarboxylation followed by Lossen's rearrangement to yield isocyanates. Described herein is the in situ trapping of the resulting isocyanates with carbon nucleophiles to synthesize β-keto amides. Furthermore, a general and mild method for the conversion of the resulting β-keto amides into quinolin-2-ones is reported.
- Vala, Anand,Parmar, Nirali,Soni, Jigar Y.,Kotturi, Sharadsrikar,Guduru, Ramakrishna
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p. 2080 - 2084
(2021/10/07)
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- Synthesis of 2-Quinolinones via a Hypervalent Iodine(III)-Mediated Intramolecular Decarboxylative Heck-Type Reaction at Room Temperature
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A hypervalent iodine(III)-mediated intramolecular decarboxylative Heck-type reaction of 2-vinyl-phenyl oxamic acids has been developed. The unique ring-strain-enabled radical decarboxylation mechanism is preliminarily revealed. This protocol features metal-free reaction conditions and operational simplicity, allowing the lactamization of 2-vinylanilines using a readily accessible carbonyl source and the synthesis of various 2-quinolinones with excellent chemoselectivity at room temperature.
- Fan, Huaqiang,Pan, Peng,Zhang, Yongqiang,Wang, Wei
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supporting information
p. 7929 - 7932
(2019/01/04)
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- Palladium-catalyzed arylation/cyclization/desulfonation cascades toward 4-aryl quinolin-2(1H)-ones with diaryliodonium salts
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Palladium-catalyzed cascades of arylation/cyclization/desulfonation of ortho-aminocinnamate esters by using diaryliodonium salts afforded a wide range of 4-aryl quinolin-2(1H)-ones. As such, the desired 4-aryl quinolin-2(1H)-ones with potential biological activity has been synthesized in the yields of 34–96%.
- Han, Jianwei,Wu, Xunshen,Zhang, Zhiang,Wang, Limin
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supporting information
p. 3433 - 3436
(2017/08/08)
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- Method for preparing 4-aryl-2-quinolinone through carbon dioxide
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The invention discloses a method for preparing 4-aryl-2-quinolinone through carbon dioxide, and belongs to the technical field of carbon dioxide comprehensive utilization. The method comprises the following concrete process steps: in a dehydrated and deox
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Paragraph 0033; 0034; 0035
(2017/04/03)
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- A Facile Synthesis of 5-Phenyl-Dibenzo[b, g][1,8]Napthyridines
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The Vilsmeier Haack heterocyclization of 2-aryl amino-4-phenyl quinolines quinoline yielded the hitherto unknown 5-phenyl-dibenzo[b,g][1,8]naphthyridines in quantitative yield. The synthesis of aryl amines was achieved by the action of anilines on 2-chloro-4-phenyl quinoline, which in turn was sourced through the combes reaction of benzoyl acetanilides.
- Sampathkumar, Natarajan,Murugesh, Arumugam,Rajendran, Subramaniam Parameswaran
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p. 924 - 928
(2016/05/19)
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- Palladium-Catalyzed Multi-Component Reactions of N-Tosylhydrazones, 2-Iodoanilines and CO2towards 4-Aryl-2-Quinolinones
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A palladium-catalyzed three-component reaction between N-tosylhydrazones, 2-iodoanilines and atmospheric pressure CO2was developed whereby a tandem carbene migration insertion/lactamization strategy afforded 4-aryl-2-quinolinones in moderate to good yields. Notably, a wide range of functional groups were tolerated in this procedure. This protocol features the simultaneous formation of four novel bonds; two C?C, one C=C and one C?N (amide), representing an efficient methodology for incorporation of CO2into heterocycles.
- Sun, Song,Hu, Wei-Ming,Gu, Ning,Cheng, Jiang
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supporting information
p. 18729 - 18732
(2016/12/26)
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- Lactamization of sp2C?H Bonds with CO2: Transition-Metal-Free and Redox-Neutral
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The first direct use of carbon dioxide in the lactamization of alkenyl and heteroaryl C?H bonds to synthesize important 2-quinolinones and polyheterocycles in moderate to excellent yields is reported. Carbon dioxide, a nontoxic, inexpensive, and readily available greenhouse gas, acts as an ideal carbonyl source. Importantly, this transition-metal-free and redox-neutral process is eco-friendly and desirable for the pharmaceutical industry. Moreover, these reactions feature a broad substrate scope, good functional group tolerance, facile scalability, and easy product derivatization.
- Zhang, Zhen,Liao, Li-Li,Yan, Si-Shun,Wang, Lei,He, Yun-Qi,Ye, Jian-Heng,Li, Jing,Zhi, Yong-Gang,Yu, Da-Gang
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supporting information
p. 7068 - 7072
(2016/07/06)
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- Practical route to 2-quinolinones via a Pd-catalyzed C-H bond activation/C-C bond formation/cyclization cascade reaction
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Quinolinone derivatives were constructed via a Pd-catalyzed C-H bond activation/C-C bond formation/cyclization cascade process with simple anilines as the substrates. This finding provides a practical procedure for the synthesis of quinolinone-containing alkaloids and drug molecules. The utility of this method was demonstrated by a formal synthesis of Tipifarnib.
- Wu, Junliang,Xiang, Shaohua,Zeng, Jing,Leow, Minli,Liu, Xue-Wei
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supporting information
p. 222 - 225
(2015/01/30)
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- A straight forward synthesis of 4-aryl substituted 2-quinolones via Heck reaction
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A variety of aryl halides have been successfully coupled with different olefins via Heck reaction in the presence of an active stimulant (Pd-NHC). An efficient one pot protocol for the easy access of structurally diverse 4-aryl-2-quinolones via domino Heck/cyclization reaction has been developed. This journal is
- Gupta, Sumanta,Ganguly, Bhaskar,Das, Sajal
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p. 41148 - 41151
(2015/02/05)
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- 4-Aryl-2-quinolones from 3,3-diarylacrylamides through intramolecular copper-catalyzed C-H functionalization/C-N bond formation
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Free NH 3,3-diarylacrylamides are cyclized to substituted 2-quinolones in the presence of CuI, PPh3, and KO-t-Bu in o-xylene at 100 °C. The reaction proceeds through a C-H functionalization/C-N bond formation process. With unsymmetrical 3,3-diarylacrylamides, high selectivity is observed using substrates where the aromatic ring trans to the amide group bears o-methyl, -chloro, or -bromo substituents.
- Berrino, Roberta,Cacchi, Sandro,Fabrizi, Giancarlo,Goggiamani, Antonella
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experimental part
p. 2537 - 2542
(2012/05/05)
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- An efficient synthesis of 4-arylquinolin-2(1 H)-ones and 3-alkenyl-4-arylquinolin-2(1 H)-one using a Pd/NiFe2O 4-catalyzed consecutive Heck reaction
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A convenient one-pot method for the synthesis of 4-arylquinolin-2(1H)-ones and 4-arylcoumarins has been described. The successive Heck reaction on substituted 2-iodoaniline and 2-iodophenol catalyzed by a Pd/nickel ferrite catalyst followed by in situ cyc
- Borhade, Sanjay R.,Waghmode, Suresh B.
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experimental part
p. 1355 - 1363
(2011/12/13)
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- Palladium-catalyzed intramolecular amidation of C(sp2)-H bonds: Synthesis of 4-aryl-2-quinolinones
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Figure presented A catalytic synthetic approach for the synthesis of 2-quinolinone compounds through a Pd-catalyzed C(sp2)-H functionalization/intramolecular amidation sequence is described. The cyclization process efficiently proceeds in the p
- Inamoto, Kiyofumi,Saito, Tadataka,Hiroya, Kou,Doi, Takayuki
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supporting information; experimental part
p. 3900 - 3903
(2010/07/05)
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- 4-Aryl-2-quinolones through a Pseudo-Domino Heck/Buchwald-Hartwig reaction in a molten tetrabutylammonium acetate/ tetrabutylammonium bromide mixture
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4-Aryl-2-quinolones can be prepared from readily available o-bromocinnamamide and aryl iodides using phosphine-free palladium(II) ace-tate as the precatalyst and a molten tetra(n-butyl)-ammonium acetate/tetra(n-butyl) ammonium bro-mide mixture as the reac
- Battistuzzi, Gianfranco,Bernini, Roberta,Cacchi, Sandro,De Salve, Ilse,Fabrizi, Giancarlo
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p. 297 - 302
(2008/02/05)
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- 4-Aryl-2-quinolones via a domino heck reaction/cyclization process
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The reaction of methyl β-(o-acetamidophenyl)acrylates with aryl iodides in the presence of Pd(OAc)2 and KOAc in DMF at 120 °C affords 4-aryl-2-quinolones in allowable to good yields.
- Bernini, Roberta,Cacchi, Sandro,Fabrizi, Giancarlo,Sferrazza, Alessio
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- The Heck reaction of β-arylacrylamides: An approach to 4-aryl-2-quinolones
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The Heck reaction of β-arylacrylamides with aryl iodides afforded the corresponding vinylic substitution products usually in high yields. The nature of β-substituents, aryl iodides and substituents at the nitrogen atom influences the stereochemical outcome. N,N-Dimethyl-β-arylacrylamides gave vinylic substitution products with higher stereoselectivity than the corresponding N-unsubstituted β-arylacrylamides. β-Arylacrylamides containing ortho-substituents led to the formation of only one stereoisomer. The procedure was used to prepare 4-aryl-2-quinolones from β-(obromophenyl) acrylamide through a sequential Heck reaction and copper-catalyzed cyclization process. Georg Thieme Verlag Stuttgart.
- Bernini, Roberta,Cacchi, Sandro,De Salve, Ilse,Fabrizi, Giancarlo
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p. 2947 - 2952
(2008/02/12)
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- The formation of quinolin-2(1H)-ones via electrocyclic reaction of o-isocyanatostyrenes generated in situ from o-isocyanostyrenes
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A convenient one-pot preparation of 4-substituted or 3,4-disubstituted quinolin-2(1H)-ones from 2-isocyanostyrene derivatives, which involves mCPBA oxidation to the corresponding isocyanate intermediates followed by electrocyclization, is described.
- Kobayashi, Kazuhiro,Kitamura, Taichi,Yoneda, Keiichi,Morikawa, Osamu,Konishi, Hisatoshi
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p. 798 - 799
(2007/10/03)
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- Synthesis of 2-Hydroxyquinolines from 2-Aminobenzophenones and N,N-Dimethylacetamide
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Substituted 2-hydroxyquinolines were obtained by interaction of 2-aminobenzophenones with N,N-dimethylacetamide under the action of powdered freshly melted potassium hydroxide at room temperature.
- Chorbadjiev, S.
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p. 3497 - 3505
(2007/10/02)
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