- PEG-400 as a carbon synthon: Highly selective synthesis of quinolines and methylquinolines under metal-free conditions
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A metal-free, peroxide-free, and efficient procedure for the highly selective synthesis of quinolines and methylquinolines was reported. The main feature of this method was that the same substrate can produce quinolines and methylquinolines, respectively, under different reaction conditions. PEG-400 was used as both a reactant and solvent in this reaction. The utility of the designed procedure was also demonstrated by the derivatization of the products to bioactive compounds. This journal is
- Ding, Chengcheng,Feng, Kaili,Li, Shichen,Ma, Chen
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p. 5542 - 5548
(2021/08/16)
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- Copper-mediated formal [5+1] annulation of 2-vinylanilines and glyoxylic acid: A facile approach for the synthesis of 4-arylated quinolines
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A copper-mediated formal [5 + 1] oxidative annulation of 2-vinylanilines and glyoxylic acid to 4-arylated quinolines was developed. A series of 4-arylated quinoline derivatives were obtained in good to excellent yields. This protocol could be carried out efficiently on gram scale. The transformation probably underwent nucleophilic addition/6π electrocyclization/oxidative aromatization and the elimination of CO2 cascade processes.
- Xiang, Yunyu,Luo, Puying,Hao, Tianxin,Xiong, Weikang,Song, Xiaolin,Ding, Qiuping
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- DMSO/t-BuONa/O2-Mediated Aerobic Dehydrogenation of Saturated N-Heterocycles
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Aromatic N-heterocycles such as quinolines, isoquinolines, and indolines are synthesized via sodium tert-butoxide-promoted oxidative dehydrogenation of the saturated heterocycles in DMSO solution. This reaction proceeds under mild reaction conditions and has a good functional group tolerance. Mechanistic studies suggest a radical pathway involving hydrogen abstraction of dimsyl radicals from the N-H bond or α-C-H of the substrates and subsequent oxidation of the nitrogen or α-aminoalkyl radicals.
- Cai, Hu,Tan, Wei,Xie, Yongfa,Yang, Ruchun,Yue, Shusheng
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p. 7501 - 7509
(2020/07/07)
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- Direct Synthesis of Quinolines via Co(III)-Catalyzed and DMSO-Involved C-H Activation/Cyclization of Anilines with Alkynes
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A unique Co(III)-catalyzed and DMSO-involved C-H activation/cyclization of simple, cheap, and easily available anilines with alkynes for direct and highly efficient synthesis of privileged quinolines with exclusive regioselectivity and broad substrate/functional group tolerance and in good to excellent yields, where DMSO was employed as both the solvent and the C1 building block of quinoline products, is reported. Mechanistic experiments revealed that the versatile reaction might employ the 2-vinylbenzenamine species as the active intermediate.
- Xu, Xuefeng,Yang, Yurong,Zhang, Xu,Yi, Wei
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supporting information
p. 566 - 569
(2018/02/10)
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- Direct Assembly of 4-Substituted Quinolines with Vinyl Azides as a Dual Synthon via C=C and C-N Bond Cleavage
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An unprecedented Zn-promoted selective cleavage of vinyl azides for the synthesis of 4-substituted quinolines is developed. In this conversion, vinyl azides function as a dual synthon via C=C and C-N bond cleavage with two C=C bonds and one C=N bond formation in a one-step manner. The reaction is appreciated for its readily accessible substrates, high step economy, mild conditions, and use of air as the sole oxidant.
- Cen, Jinghe,Li, Jianxiao,Zhang, Yu,Zhu, Zhongzhi,Yang, Shaorong,Jiang, Huanfeng
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supporting information
p. 4434 - 4438
(2018/08/07)
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- Synthesis of quinolines from anilines, acetophenones and DMSO under air
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An efficient CH3SO3H-promoted synthesis of quinolines from readily available anilines, acetophenones and DMSO under air is reported. This protocol gives diverse substituted 4-arylquinolines in moderate to high yields with broad substrate/functional group tolerance. Preliminary mechanistic studies demonstrate that DMSO may be transformed to HCHO in this process and used as a one carbon source.
- Jiang, Tao-Shan,Wang, Xi,Zhang, Xiuli
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supporting information
p. 2979 - 2982
(2018/06/29)
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- Carbon annulation of ortho-vinylanilines with dimethyl sulfoxide to access 4-aryl quinolines
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A palladium-catalyzed annulation of ortho-vinylanilines with dimethyl sulfoxide was developed to access 4-aryl quinolines in moderate to good yields. Activated by 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABSO), DMSO served as a “=CH-” fragment in this transformation. It represents a facile pathway leading to 4-aryl quinolines.
- Yuan, Jin,Yu, Jin-Tao,Jiang, Yan,Cheng, Jiang
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p. 1334 - 1337
(2017/02/15)
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- Silver-Catalyzed Minisci Reactions Using Selectfluor as a Mild Oxidant
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A new method for silver-catalyzed Minisci reactions using Selectfluor as a mild oxidant is reported. Heteroarenes and quinones both participate in radical C-H alkylation and arylation from a variety of carboxylic and boronic acid radical precursors. Several oxidatively sensitive and highly reactive radical species are successful, providing structures that are challenging to access by other means.
- Galloway, Jordan D.,Mai, Duy N.,Baxter, Ryan D.
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supporting information
p. 5772 - 5775
(2017/11/10)
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- Silver-catalyzed three-component approach to quinolines starting from anilines, aldehydes, and alcohols
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A silver-catalyzed sequential formation of two C-C bonds for the construction of a series of polysubstituted quinolines from anilines, aldehydes, and alcohols under mild conditions has been developed. The transformation is effective for a broad range of substrates, including aliphatic alcohols, arylalkanols, cycloalkanols, and ethylene glycol, thereby permitting the expansion of the constituent architectures of the heterocyclic framework.
- Zhang, Xu,Liu, Wenmin,Sun, Ruixue,Xu, Xuefeng,Wang, Zhiqiang,Yan, Yanlei
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p. 1563 - 1568
(2016/06/14)
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- HOTf-catalyzed intermolecular hydroamination reactions of alkenes and alkynes with anilines
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Herein, the intermolecular hydroamination of alkenes and alkynes with anilines catalyzed by HOTf under mild conditions has been developed. This reaction provides one of the simplest alkene and alkyne addition methods and is an alternative to metal-catalyzed reactions. At the same time, the intramolecular hydroamination of alkynes with anilines proceeds smoothly to obtain quinolines. We found that this strategy is efficient in building complex structures from simple starting materials in an environmentally benign fashion.
- Xu, Xuefeng,Zhang, Xu,Wang, Zhiqiang,Kong, Manman
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p. 40950 - 40952
(2015/05/20)
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- Silver-catalyzed oxidative coupling of aniline and ene carbonyl/acetylenic carbonyl compounds: An efficient route for the synthesis of quinolines
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An efficient silver-mediated coupling of aniline with ene carbonyl/acetylenic carbonyl compounds for the synthesis of quinolines is reported. The transformation is effective for a broad range of substrates, thus enabling the expansion of substituent architectures on the heterocyclic framework. The electronic properties of the substituents on the amine have been investigated. It was found that molecules with both electron-donating and electron-withdrawing substituents were suitable substrates for this transformation, and the expected products were obtained in moderate to excellent yields. The use of a single catalytic system to mediate chemical transformations in a synthetic operation is important for the development of new atom-economic strategies and this strategy is efficient in building complex structures from simple starting materials in an environmentally benign fashion.
- Zhang, Xu,Xu, Xuefeng
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supporting information
p. 3089 - 3093
(2015/02/19)
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- Iron-catalyzed direct C-H arylation of heterocycles and quinones with arylboronic acids
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The arylation of C-H bonds to generate heteroaryl-aryl (Het-Ar) and arylated quinone (Quin-Ar) compounds has received great attention to achieve sustainable goals in synthetic chemistry. Despite significant advances, arylation of a broad range of Het-Ar and Quin-Ar derivatives remains a challenging task. Herein, a variety of heterocycles are arylated by using arylboronic acids in the presence of catalytic amounts of inexpensive Fe(NO 3)3. The C-arylated quinone compounds can be prepared by reacting arylboronic acids with either quinone or hydroquinone. The present method is operationally simple, scalable, does not require prefunctionalization of the heterocycle or quinone, and can tolerate a wide variety of functional groups in the coupling partners. These qualities are expected to render this method attractive for academic and industrial use. Direct C-H arylation of a variety of heterocycles and quinones with arylboronic acids has been developed. An inexpensive iron catalyst, Fe(NO3)3, and a co-oxidant, persulfate, were used in air. The protocol is applicable for large-scale synthesis and is expected to find application as a result of its operational simplicity. Copyright
- Deb, Arghya,Manna, Srimanta,Maji, Arun,Dutta, Uttam,Maiti, Debabrata
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supporting information
p. 5251 - 5256
(2013/09/02)
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- Molecular iodine-catalyzed and air-mediated tandem synthesis of quinolines via three-component reaction of amines, aldehydes, and alkynes
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A one-pot synthesis of quinolines via molecular iodine-catalyzed and air-mediated tandem condensation/imino-Diels-Alder/isomerization/oxidation of simple readily available amines, aldehydes, and alkynes has been developed. This methodology was extended to synthesize quinazolines from two molecules of amines and two molecules of glyoxalates.
- Li, Xuejian,Mao, Zhenjun,Wang, Yanguang,Chen, Weixiang,Lin, Xufeng
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experimental part
p. 3858 - 3862
(2011/06/21)
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- Radical Annulations and Cyclisations with Isonitriles: the Fate of the Intermediate Imidoyl and Cyclohexadienyl Radicals
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The reaction of 4-methoxyphenylisonitrile with phenylacetylene and AIBN produces a novel cyclopenta-fused quinoxalin through addition of 2-cyanoprop-2-yl radical to the alkyne; the resultinge vinyl radical attacks isonitrile to afford an imidoyl radical, which gives rise to a tandem 5-exo, 6-endo cyclisation.The whole process entails a new example of a rare 4 + 1 radical annulation.The cyanopropyl radical can also attack isonitrile to yield small amounts of quinolines deriving from 4 + 2 and 3 + 2 annulation between the resulting imidoyl radicals and phenylacetylene.The oxidation step leading to the final aromatic products involves the starting isonitrile, which is converted to an α-unsubstituted imidoyl radical and affords 2-unsubstituted quinolines.This behaviour was also found in cyclisations of biphenyl-2-ylisonitrile under various radical conditions.Finally, the title reaction gives small ammounts of an α,β-unsaturated nitrile, which can arise from a spirocyclohexadienyl radical through fragmentation and subsequent β-scission of the resulting iminyl.This could be the first, direct evidence of the intermediacy of iminyl radicals in the rearrangements of the spirocyclohexadienyls obtained by 3 + 2 annulation between imidoyl radicals and alkynes.
- Nanni, Daniele,Pareschi, Patrizia,Rizzoli, Corrado,Sgarabotto, Paolo,Tundo, Antonio
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p. 9045 - 9062
(2007/10/02)
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- The Reactions of Aromatic Schiff Bases with Dimethyl Acetylenedicarboxylate. I. Reaction in an Organic Solvent
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Reaction of benzylideneanisidine with dimethyl acetylenedicarboxylate in refluxing xylene/nitrobenzene gave low yields of a bis-adduct, the dihydropyridine (12), and two dehydro adducts - the quinolines (13a) and (14).Anisylideneaniline under similar conditions gave the dihydropyridine (16) and an 'abnormal' bis-adduct.Benzylideneaniline gave only an 'abnormal' bis-adduct.
- Murphy, Shane T.,Taylor, Walter C.,Vadasz, Andrew
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p. 1215 - 1225
(2007/10/02)
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