- [3+1+1+1] Annulation to the Pyridine Structure in Quinoline Molecules Based on DMSO as a Nonadjacent Dual-Methine Synthon: Simple Synthesis of 3-Arylquinolines from Arylaldehydes, Arylamines, and DMSO
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A [3+1+1+1] annulation of arylamines, arylaldehydes, and dimethyl sulfoxide (DMSO) to the pyridine structure in quinolines using DMSO as a nonadjacent dual-methine (═CH?) synthon is disclosed. In this annulation, arylamines provide two carbon atoms and one nitrogen atom, arylaldehydes furnish one carbon atom, and DMSO provides two nonadjacent methines (═CH?) to the pyridine ring in quinoline molecules. This annulation provides a simple approach for the synthesis of 3-arylquinolines from readily available substrates in useful yields. On the basis of the control experiments and the literature, a plausible mechanism is proposed.
- Guo, Can-Cheng,Li, Hui,Liu, Qiang,Luo, Wei-Ping,Nie, Zhiwen,Su, Miao-Dong,Yang, Tonglin
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- Method for preparing 3 - arylquinoline
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The invention discloses a method for preparing 3 - arylquinoline, which is carried out in an oxygen-containing atmosphere, ortho-amine arylmethanol and aryl formaldehyde in DMSO-solution system containing an alkali to obtain 3 -arylquinoline compounds. In 3 - arylquinoline compound structure prepared by the method, 2 carbon atoms are provided by DMSO, aryl groups at 3 carbon atoms and 3 positions are provided by aryl formaldehyde, and all other atoms in the quinoline compound structure are provided by raw material o-amido aryl methanol. The method for synthesizing 3 - arylquinoline has the advantages of wide raw material sources, environmental friendliness, low price and simple operation, and is beneficial to industrial production.
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Paragraph 0047; 0048; 0051; 0053; 0054; 0144-0146
(2021/11/26)
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- Carbon Atom Insertion into Pyrroles and Indoles Promoted by Chlorodiazirines
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Herein, we report a reaction that selectively generates 3-arylpyridine and quinoline motifs by inserting aryl carbynyl cation equivalents into pyrrole and indole cores, respectively. By employing α-chlorodiazirines as thermal precursors to the corresponding chlorocarbenes, the traditional haloform-based protocol central to the parent Ciamician-Dennstedt rearrangement can be modified to directly afford 3-(hetero)arylpyridines and quinolines. Chlorodiazirines are conveniently prepared in a single step by oxidation of commercially available amidinium salts. Selectivity as a function of pyrrole substitution pattern was examined, and a predictive model based on steric effects is put forward, with DFT calculations supporting a selectivity-determining cyclopropanation step. Computations surprisingly indicate that the stereochemistry of cyclopropanation is of little consequence to the subsequent electrocyclic ring opening that forges the pyridine core, due to a compensatory homoaromatic stabilization that counterbalances orbital-controlled torquoselectivity effects. The utility of this skeletal transform is further demonstrated through the preparation of quinolinophanes and the skeletal editing of pharmaceutically relevant pyrroles.
- Dherange, Balu D.,Kelly, Patrick Q.,Levin, Mark D.,Liles, Jordan P.,Sigman, Matthew S.
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supporting information
p. 11337 - 11344
(2021/08/16)
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- Cobalt(III)-Catalyzed, DMSO-Involved, and TFA-Controlled Regioselective C?H Functionalization of Anilines with Alkynes for Specific Assembly of 3-Arylquinolines
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Herein, a novel cobalt(III)-catalyzed and TFA-controlled [3+2+1] cyclization of diverse anilines and terminal alkynes has been realized by using DMSO as both the solvent and the C1 source, which led to the specific synthesis of privileged 3-arylquinolines in one pot and regioselectively. Mechanistic investigations revealed that this versatile transformation might be initiated with a C?H activation process and with a 2-vinylbenzenamine species as the active intermediate. (Figure presented.).
- Zhang, Peiquan,Yang, Yurong,Chen, Zhiyong,Xu, Zhang,Xu, Xuefeng,Zhou, Zhi,Yu, Xiyong,Yi, Wei
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supporting information
p. 3002 - 3007
(2019/04/30)
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- Inhibitors of the detoxifying enzyme of the phytoalexin brassinin based on quinoline and isoquinoline scaffolds
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The detoxification of the phytoalexin brassinin to indole-3-carboxaldehyde and S-methyl dithiocarbamate is catalyzed by brassinin oxidase (BOLm), an inducible fungal enzyme produced by the plant pathogen Leptosphaeria maculans. Twenty-six substituted quinolines and isoquinolines are synthesized and evaluated for antifungal activity against L. maculans and inhibition of BOLm. Eleven compounds that inhibit BOLm activity are reported, of which 3-ethyl-6-phenylquinoline displays the highest inhibitory effect. In general, substituted 3-phenylquinolines show significantly higher inhibitory activities than the corresponding 2-phenylquinolines. Overall, these results indicate that the quinoline scaffold is a good lead to design paldoxins (phytoalexin detoxification inhibitors) that inhibit the detoxification of brassinin by L. maculans.
- Pedras, M. Soledade C.,Abdoli, Abbas,Sarma-Mamillapalle, Vijay K.
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- Regioselective Synthesis of C-3-Functionalized Quinolines via Hetero-Diels-Alder Cycloaddition of Azadienes with Terminal Alkynes
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A highly efficient metal and protection-free approach for the regioselective synthesis of C-3-functionalized quinolines from azadienes (in situ generated from 2-aminobenzyl alcohol) and terminal alkynes through [4 + 2] cycloaddition has been developed. An unprecedented reaction of 2-aminobenzyl alcohol with 1,3- and 1,4-diethynylbenzene provided the C-3 tolylquinolines via [4 + 2] HDA and oxidative decarboxylation. The -NH2 group directed mechanistic approach was well supported by the control experiments and deuterium-labeling studies and by isolating the azadiene intermediate. The reactivity and selectivity of unprotected azadiene in metal-free base-assisted hetero-Diels-Alder reaction is exploited to quickly assemble an important class of C-3-functionalized quinolines, which are difficult to access.
- Saunthwal, Rakesh K.,Patel, Monika,Verma, Akhilesh K.
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p. 6563 - 6572
(2016/08/16)
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- Copper-catalyzed synthesis of substituted quinolines via C-N coupling/condensation from ortho -acylanilines and alkenyl iodides
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An efficient cascade copper-catalyzed intermolecular Ullmann-type C-N coupling/enamine condensation reaction is described, in which ortho-acylanilines and alkenyl iodides converted to multisubstituted quinolines in good to excellent yields.
- Kong, Lingkai,Zhou, Yuanyuan,Huang, He,Yang, Yang,Liu, Yuanyuan,Li, Yanzhong
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p. 1275 - 1278
(2015/01/30)
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- Metal-free, ionic liquid-mediated synthesis of functionalized quinolines
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An expedient and metal-free synthetic protocol for construction of substituted quinolines has been developed from anilines and phenylacetaldehydes using imidazolium cation-based ionic liquids as the reaction medium. Mechanistic analysis indicated that the reaction occurs through C-C and C-N bond formation to produce isolable 2,3-disubstituted quinoline intermediates, which undergo C-C bond cleavage to produce 3-substituted quinolines. The reaction proceeds smoothly with a range of functionalities in good to excellent yields. Advantages of this protocol include metal-free, environmentally friendly, recyclable reaction media, higher yields and shorter reaction times, and thus is promising for the efficient combinatorial synthesis of structurally diverse 2,3-disubstituted and 3-substituted quinolines.
- Bharate, Jaideep B.,Bharate, Sandip B.,Vishwakarma, Ram A.
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supporting information
p. 624 - 630
(2015/02/19)
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- Iron-promoted tandem reaction of anilines with styrene oxides via C-C cleavage for the synthesis of quinolines
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A novel iron-promoted tandem reaction of anilines with styrene oxides via C-C cleavage and C-H activation has been developed. The reaction utilizes an inexpensive FeCl3 as promoter and is suitable for forming a variety of 3-arylquinolines from
- Zhang, Yicheng,Wang, Min,Li, Pinhua,Wang, Lei
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supporting information; experimental part
p. 2206 - 2209
(2012/06/18)
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- A novel Friedlander-type synthesis of 3-aryl quinolines from 3-oxo-2,3-diaryl-propionaldehydes
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3-Aryl quinolines are readily synthesized by a novel Friedlaender-type reaction with 3-oxo-2,3-diaryl-propionaldehydes and 2-amino arylaldehydes. A preliminary mechanism of this novel one pot, two-step synthesis has been explored with the proofs of isolation of the enaminone intermediate and the eliminated benzoic acid in this reaction.
- Luo, Wanrong,Mu, Qiuchao,Qiu, Wenwei,Liu, Ting,Yang, Fan,Liu, Xiaofeng,Tang, Jie
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supporting information; experimental part
p. 7090 - 7095
(2011/10/07)
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- INDOLE DERIVATIVES FOR TREATING VIRAL INFECTIONS
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Disclosed are compounds having formula I and related compositions and methods thereof. The compounds are useful for treating viral infections caused by the Flaviviridae family of viruses.
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Page/Page column 153
(2008/06/13)
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