- An efficient synthesis of substituted quinolines via indium(III) chloride catalyzed reaction of imines with alkynes
-
An efficient synthetic method for the preparation of quinolines through indium(III) chloride-catalyzed tandem addition-cyclization-oxidation reactions of imines with alkynes was developed. The processes can provide a diverse range of quinoline derivatives
- Zhu, Mei,Fu, Weijun,Xun, Chen,Zou, Guanglong
-
-
Read Online
- Visible-Light-Mediated Oxidative Cyclization of 2-Aminobenzyl Alcohols and Secondary Alcohols Enabled by an Organic Photocatalyst
-
This paper describes a visible-light-mediated oxidative cyclization of 2-aminobenzyl alcohols and secondary alcohols to produce quinolines at room temperature. This photocatalytic method employed anthraquinone as an organic small-molecule catalyst and DMSO as an oxidant. According to this present procedure, a series of quinolines were prepared in satisfactory yields.
- Xu, Jing-Xiu,Pan, Nan-Lian,Chen, Jia-Xi,Zhao, Jin-Wu
-
-
Read Online
- Synthesis of substituted 1,2-dihydroquinolines and quinolines from aromatic amines and alkynes by gold(I)-catalyzed tandem hydroamination-hydroarylation under microwave-assisted conditions
-
Equation Presented A method to efficiently prepare substituted 1,2-dihydroquinolines and quinolines by Au(I)-catalyzed tandem hydroamination-hydroarylation under microwave irradiation was developed. This method requires short reaction time (10-70 min) and
- Liu, Xin-Yuan,Ding, Pan,Huang, Jie-Sheng,Che, Chi-Ming
-
-
Read Online
- Divergent Functionalization of N-Alkyl-2-alkenylanilines: Efficient Synthesis of Substituted Indoles and Quinolines
-
An efficient divergent functionalization of N-alkylated ortho-alkenylanilines to substituted indoles and quinolines has been accomplished by employing rhodium-catalyzed cross-dehydrogenative coupling and silver-mediated oxidative cyclization, respectively. The developed methods tolerate various functional groups and allow the synthesis of substituted indoles and quinolines in good to excellent yield. Synthetic utility is demonstrated through conversion to an indole with antimicrobial activity and C?H bond functionalization of 2-arylquinolines. Furthermore, a plausible mechanism was proposed based on preliminary mechanistic investigations.
- Ghorai, Jayanta,Reddy, Angula Chandra Shekar,Anbarasan, Pazhamalai
-
-
Read Online
- N-Heterocyclic carbene copper catalyzed quinoline synthesis from 2-aminobenzyl alcohols and ketones using DMSO as an oxidant at room temperature
-
A facile and practical process for the synthesis of quinolines through an N-heterocyclic carbene copper catalyzed indirect Friedl?nder reaction from 2-aminobenzyl alcohol and aryl ketones using DMSO as an oxidant at room temperature is reported. A series of quinolines were synthesized in acceptable yields.
- Xu, Jingxiu,Chen, Qingmao,Luo, Zhigao,Tang, Xiaodong,Zhao, Jinwu
-
-
Read Online
- Mn(III)-Mediated Regioselective 6-endo-trig Radical Cyclization of o-Vinylaryl Isocyanides to Access 2-Functionalized Quinolines
-
A Mn(III)-mediated radical cyclization reaction of o-vinylaryl isocyanides and arylboronic acids or diphenylphosphine oxides to access various 2-functionalized quinolines under mild conditions was developed. With the introduction of radical stabilizing substituents (e. g. aryl and methyl group) on vinyl group, this reaction provides a regiospecific 6-endo-trig radical cyclization of o-vinylaryl isocyanides, giving a number of structurally unique and biologically potential 2-functionalized quinoline derivatives.
- Liu, Yan,Li, Shi-Jun,Chen, Xiao-Lan,Fan, Lu-Lu,Li, Xiao-Yun,Zhu, Shan-Shan,Qu, Ling-Bo,Yu, Bing
-
-
Read Online
- Copper(I)- And gold(I)-catalyzed synthesis of 2,4-disubstituted quinoline derivatives from N-Aryl-2-propynylamines
-
2,4-Disubstituted quinoline derivatives were obtained from N-aryl-2-propynylamines catalyzed by copper(I) and gold(I) complexes. The quinoline derivatives could also be obtained by the reaction of N-arylaldimines with terminal acetylenes via the formation of N-aryl-2-propynylamines. Copyright
- Kuninobu, Yoichiro,Inoue, Yuichi,Takai, Kazuhiko
-
-
Read Online
- Metal-Free Synthesis of 2-Substituted Quinolines via High Chemoselective Domino Condensation/Aza-Prins Cyclization/Retro-Aldol between 2-Alkenylanilines with β-Ketoesters
-
A highly chemoselective domino condensation/aza-Prins cyclization/retro-aldol between 2-alkenylanilines with β-dicarbonyl compounds under metal-free conditions was accomplished, giving a large category of valuable 2-substituted quinolines in good yields with excellent functional group toleration. This newly established process, adopting β-ketoesters as masked C1 synthons via C-C cleavage, could even be simplified into a three-component [3 + 2 + 1] domino version consisting of exceedingly low-priced commercial starting materials. The synthetic application of products was exemplified by several intriguing chemical operations.
- Nan, Jiang,Chen, Pu,Zhang, Yuxin,Yin, Yun,Wang, Bo,Ma, Yangmin
-
-
Read Online
- Synthesis of quinolines via acceptorless dehydrogenative tandem cyclization of 2-amionbenzyl alcohol with alcohols using magnetic CuNiFeO nanocatalyst
-
This work reports the preparation of nano CuNiFeO and its application in the synthesis of quinolines. The prepared nanocatalyst was characterized using various characterization techniques such as XRD, FEG-SEM, EDX, HR-TEM and XPS. Nano CuNiFeO as a heterogeneous catalyst shows a very high efficiency towards double dehydrogenation tandem cyclization reaction of 2-amionbenzyl alcohol with alcohols resulting into a simple, sustainable and environment friendly synthesis of quinolines. Due to the magnetic property associated with nanocatalyst, it was easily separated from the reaction mixture using external magnet and could be reused up to five cycles. To the best of our knowledge, this is for the first time a heterogenous magnetic CuNiFeO nanocatalyst is being reported for this reaction.
- Chaurasia, Shivkumar R.,Tiwari, Abhishek R.,Bhanage, Bhalchandra M.
-
-
Read Online
- Silver-catalyzed cascade reaction of o-aminoaryl compounds with alkynes: An aniline mediated synthesis of 2-substituted quinolines
-
An efficient silver-catalyzed, aniline mediated cascade hydroamination/cycloaddition of o-aminoaryl compounds including o-aminoaryl aldehydes, o-aminoaryl ketones with alkynes for the synthesis of 2- or 2,4-substituted quinolines is reported. The reactions proceed with high regioselectivity to afford mono- or disubstituted quinoline derivatives in good to high yields using AgOTf as the catalyst in the air.
- Li, Hongfeng,Wang, Chengyu,Huang, He,Xu, Xiaolei,Li, Yanzhong
-
-
Read Online
- Synthesis of 3-Organoseleno-Substituted Quinolines through Cyclization of 2-Aminophenylprop-1-yn-3-ols Promoted by Iron(III) Chloride with Diorganyl Diselenides
-
We have described the application of iron(III) chloride and diorganyl diselenides as cooperative partners in the cyclization of (2-aminoaryl)-2-ynols for the regioselective synthesis of 3-organoseleno quinolines. The optimized reaction conditions were app
- Stein, André Luiz,Rosário, Alisson Rodrigues,Zeni, Gilson
-
-
Read Online
- The use of 2-vinylanilines in the synthesis of indole- and quinoline-derivatives
-
Cyclization reactions of 2-vinylaniline derivatives, proceeding via anils, amides, imidic acid esters, ureas, thioureas, carbodiimides, formamidine ylids, sulfonamides or ketenes, leading to quinoline or indole derivatives, are described. In a short intro
- Walter, Harald
-
-
Read Online
- 1H and 13C NMR spectral studies of some 2,4-diphenylquinoline derivatives
-
The 400 MHz 1H and 14 MHz 13C NMR spectra of a series of 2,4-diphenylquinoline derivatives are presented.The characteristic H-3 and ipso-phenyl carbon signals are the most useful for the identification of these compounds.The effects of a peri-phenyl/methy
- Osborne, A. G.
-
-
Read Online
- Selective Aza Diels-Alder and Domino [4+2]/[2+2] Cycloaddition Reactions of Arynes with N-Sulfonyl Ketimines
-
Transition-metal-free inverse electron-demand aza Diels-Alder and domino [4+2]/[2+2] cycloaddition reaction of arynes and N-sulfonyl ketimines has been demonstrated. This novel, mild, and efficient protocol allows rapid access to isothiazole dioxide-fused
- Kiran, I. N. Chaithanya,Reddy, R. Santhosh,Lagishetti, Chandraiah,Xu, Huacheng,Wang, Zhen,He, Yun
-
-
Read Online
- An approach for quinolines via palladium-catalyzed Heck coupling followed by cyclization
-
2-Iodoaniline reacts with α,β-unsaturated carbonyl compounds in DMF at 100 °C in the presence of a catalytic amount of a palladium catalyst along with a base to afford the corresponding quinolones or quinolines in moderate to good yields.
- Cho, Chan Sik,Kim, Jun Uk
-
-
Read Online
- NOVEL SYNTHESIS OF 2,4-DIPHENYLQUINOLINES
-
2,4-Diphenylquinolines (3) were quantitatively prepared by heating of 3-aryl-4,6-diphenyl-2-oxo-1,3-diazabicyclohex-5-enes (2), which were obtained by photochemical electrocyclization of 1-aryl-4,6-diphenyl-2(1H)-pyrimidin-2-ones (1), in benzene at reflux temperature.
- Nishio, Takehiko,Katahira, Katsuhiro,Omote, Yoshimori
-
-
Read Online
- Phenanthrenequinone-Sensitized Photocatalytic Synthesis of Polysubstituted Quinolines from 2-Vinylarylimines
-
Visible-light-excited 9,10-phenanthrenequinone (PQ*) was used as a photocatalyst for the synthesis of polysubstituted quinolines via the electrocyclization of 2-vinylarylimines. Up to quantitative yields of 2,4-disubstituted quinolines were received after 1 h of excitation with blue LEDs at room temperature when MgCO3 was used as an additive in DCM. On the basis of experimental and DFT studies, we propose that PQ? induces one-electron oxidation of the imine substrate that triggers the electrocyclization mechanism.
- Talvitie, Juulia,Alanko, Iida,Bulatov, Evgeny,Koivula, Juho,P?ll?nen, Topias,Helaja, Juho
-
p. 274 - 278
(2022/01/04)
-
- Dehydrogenation of N-Heterocyclic Compounds Using H2O2 and Mediated by Polar Solvents
-
The oxidative dehydrogenation of N-heterocyclic compounds by using H2O2 as oxidant in combination with polar solvents such as 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) and H2O is described. Among these two solvents, the best yields for the heteroaromatic compounds were generally achieved in HFIP. However, it is remarkable, that the use of a non toxic solvent such as H2O gave such good yields. Furthermore, the procedure was implemented in larger-scale and HFIP was distilled from the reaction mixture and reused (up to 5 cycles) without a significant detriment in the reaction outcome. (Figure presented.).
- Llopis, Natalia,Gisbert, Patricia,Baeza, Alejandro,Correa-Campillo, Jara
-
p. 1205 - 1210
(2022/02/25)
-
- Carbocatalytic Cascade Synthesis of Polysubstituted Quinolines from Aldehydes and 2-Vinyl Anilines
-
Oxidized active carbon (oAC) catalyses the formation of polysubstituted quinolines from o-vinyl anilines and aldehydes. The reaction proceeds in a cascade manner through condensation, electrocyclization and dehydrogenation, and gives access to a wide range of quinolines with alkyl and/or aryl substituents as demonstrated with 40 examples. The metal-free catalytic procedure allows a heterogeneous protocol for the synthesis of various polysubstituted quinolines. The mechanistic studies imply that both the acid and quinoidic groups in oAC are integral for the catalytic manifold. (Figure presented.).
- Bulatov, Evgeny,Helaja, Juho,Hu, Tao,Lenarda, Anna,M?kel?, Mikko K.,Malinen, Kiia,Melchionna, Michele,Nieger, Martin,Talvitie, Juulia,Wirtanen, Tom
-
supporting information
p. 3775 - 3782
(2021/07/20)
-
- Synthesis of quinolines: Via sequential addition and I2-mediated desulfurative cyclization
-
An efficient one-pot approach for the synthesis of quinolines from o-aminothiophenol and 1,3-ynone under mild conditions is disclosed. With the aid of ESI-MS analysis and parallel experiments, a three-step mechanism is proposed - a two-step Michael additi
- Gao, Ziwei,Jian, Yajun,Sun, Huaming,Wang, Yanyan,Yang, Mingming,Zhang, Guofang,Zhang, Weiqiang
-
p. 38889 - 38893
(2021/12/20)
-
- Mild and efficient copper-catalyzed oxidative cyclization of oximes with 2-aminobenzyl alcohols at room temperature: synthesis of polysubstituted quinolines
-
A simple and efficient ligand-free Cu-catalyzed protocol for the synthesis of polysubstituted quinolinesviaoxidative cyclization of oxime acetates with 2-aminobenzyl alcohols at room temperature has been developed. The presented approach provides a new synthetic pathway leading to polysubstituted quinolines with good functional group tolerance under mild conditions. Moreover, this transformation can be applied for the preparation of quinolines on a gram scale. Oxime acetates serve as the internal oxidants in the reactions, thus making this method very attractive.
- Liu, Yan-Yun,Wei, Yang,Huang, Zhi-Hui,Liu, Yilin
-
supporting information
p. 659 - 666
(2021/02/06)
-
- Lewis acid catalyzed reactivity switch: Pseudo three-component annulation of nitrosoarenes and (epoxy)styrenes
-
A Lewis acid catalyzed annulation reaction via arene functionalization of nitrosoarenes and C-C cleavage of (epoxy)styrene to provide arylquinolines is reported. The Lewis acid catalyst altered the annulation pattern providing arylquinolines instead of oxazolidines. The reaction with styrene resulted in a mixture of 2,4-diarylquinoline and 4-Arylquinoline, while only 3-Arylquinoline was formed from the reaction of epoxystyrene. This journal is
- Purkait, Anisha,Saha, Subhajit,Ghosh, Santanu,Jana, Chandan K.
-
supporting information
p. 15032 - 15035
(2020/12/22)
-
- Superbase-Mediated Indirect Friedl?nder Reaction: A Transition Metal-Free Oxidative Annulation toward Functionalized Quinolines
-
A superbase mediated indirect Friedl?nder reaction towards functionalized quinolines has been realized. The reaction was performed with o-aminobenzyl alcohol and ketones having an active methylene moiety in the presence of KOH and in DMSO. The reaction proceeds predominantly via initial formation of an imine intermediate and subsequent oxidation of the benzyl alcohol functionality and condensation to afford substituted quinolines. We could also demonstrate that a minor fraction of the reaction proceeds via a chalcone intermediate. The transition metal-free oxidative annulation was found to be general affording 2-substituted, 2,3-disubstituted/fused or multi-substituted quinolines. The reaction was extended towards the functionalization of natural products and the applicability of the reaction for gram-scale synthesis of quinolines was also demonstrated.
- Rahul,Nitha,Omanakuttan, Vishnu K.,Babu, Sheba Ann,Sasikumar,Praveen, Vakayil K.,Hopf, Henning,John, Jubi
-
p. 3081 - 3089
(2020/05/08)
-
- Sustainable synthesis of quinolines (pyridines) catalyzed by a cheap metal Mn(I)-NN complex catalyst
-
This study represents the first example of a bidentate phosphine-free manganese(I)-NN complex catalyst for the synthesis of quinolines (pyridines) through acceptorless dehydrogenative condensation of various secondary alcohols with amino alcohols. The coupling reactions occurred at 3 mol% catalyst loading and 110°C, and tolerated diverse functional groups. Moderate to excellent yields ranging from 45% to 89% were achieved after 12 hr of reaction. The present protocol provides a concise and environmentally friendly method for the construction of heterocyclic compounds.
- Chai, Huining,Tan, Weiqiang,Lu, Yuanyuan,Zhang, Guangyao,Ma, Jiping
-
-
- Synthesis of Tetrahydroquinolines via Borrowing Hydrogen Methodology Using a Manganese PN3Pincer Catalyst
-
A straightforward and selective synthesis of 1,2,3,4-tetrahydroquinolines starting from 2-aminobenzyl alcohols and simple secondary alcohols is reported. This one-pot cascade reaction is based on the borrowing hydrogen methodology promoted by a manganese(I) PN3 pincer complex. The reaction selectively leads to 1,2,3,4-tetrahydroquinolines thanks to a targeted choice of base. This strategy provides an atom-efficient pathway with water as the only byproduct. In addition, no further reducing agents are required.
- Hofmann, Natalie,Homberg, Leonard,Hultzsch, Kai C.
-
supporting information
p. 7964 - 7970
(2020/11/02)
-
- Synthesis of phenanthridines by I2-mediated sp3C-H amination
-
An I2-mediated synthesis of phenanthridinesviaintramolecular sp3C-H amination of readily accessible aniline precursors is reported. The present synthetic process is straightforward and applicable to a broad variety of unprotected ani
- Chang, Junbiao,Fang, Benyao,Hou, Jiao,Tian, Jinyue,Yu, Wenquan
-
p. 3312 - 3323
(2020/05/14)
-
- The synthesis of quinolines: via denitrogenative palladium-catalyzed cascade reaction of o -aminocinnamonitriles with arylhydrazines
-
The first example of the palladium-catalyzed cascade reaction of o-aminocinnamonitriles with arylhydrazines has been achieved, providing an efficient synthetic pathway to access quinolines with moderate to good yields. Preliminary mechanistic experiments
- Chen, Jiuxi,Huang, Hang,Li, Renhao,Xie, Jing,Xu, Tong,Ye, Xueting
-
p. 8586 - 8593
(2020/03/13)
-
- Quinoline compound and synthesis method thereof
-
The invention discloses a synthesis method of a quinoline compound. The synthesis method comprises the following steps: adding a diazocarbonyl compound and a 2-vinylaniline compound into a solvent, carrying out a reaction under the protection of an inert
- -
-
Paragraph 0065-0069
(2020/02/14)
-
- Method for synthesizing 2-hydrocarbylquinoline
-
The invention provides a method for synthesizing 2-hydrocarbylquinoline. The method comprises the following steps: heating and reacting aniline or substituted aniline, phenylacetylene or substituted phenylacetylene and montmorillonite in chlorobenzene, ad
- -
-
Paragraph 0046; 0047; 0050-0051; 0052; 0055
(2019/10/01)
-
- Transition-Metal-Free Desulfinative Cross-Coupling of Heteroaryl Sulfinates with Grignard Reagents
-
A mild cross-coupling reaction of heteroaryl sulfinates with Grignard reagents has been developed under transition-metal-free conditions. This study provides an example of the SO22- as a leaving group in an aromatic system and an effective methodology for the construction of C-C bond.
- Wei, Jun,Liang, Huamin,Ni, Chuanfa,Sheng, Rong,Hu, Jinbo
-
-
- Pd-Catalyzed Tandem Reaction of 2-Aminostyryl Nitriles with Arylboronic Acids: Synthesis of 2-Arylquinolines
-
A novel palladium-catalyzed protocol for the synthesis of 2-arylquinolines via tandem reaction of 2-aminostyryl nitriles with arylboronic acids has been developed with good functional group tolerance. The presented approach offers a new synthetic pathway toward the core structures of 2-arylquinolines compared to classical condensation reaction of (E)-2-aminostyryl aryl ketones. Moreover, the present synthetic route could be readily scaled up to gram quantity without difficulty. Preliminary mechanistic experiments showed that this transformation involves a nucleophilic addition of aryl palladium species to the nitrile to generate an aryl ketone intermediate followed by an intramolecular cyclization and dehydration to quinoline ring.
- Xu, Tong,Shao, Yinlin,Dai, Ling,Yu, Shulin,Cheng, Tianxing,Chen, Jiuxi
-
p. 13604 - 13614
(2019/10/16)
-
- Method for preparing quinoline compounds under catalysis of zirconocene dichloride
-
The invention discloses a method for preparing quinoline compounds under catalysis of zirconocene dichloride. According to the method, 3-butyne-2-one compounds and an o-aminophenylmercaptan compound are taken as raw materials, zirconium dichloride is take
- -
-
Paragraph 0016-0023; 0048-0053
(2019/09/14)
-
- One-pot synthesis of 2,4-disubstituted quinolines via silver-catalyzed three-component cascade annulation of amines, alkyne esters and terminal alkynes
-
Described herein is a new and general method for one-pot synthesis of 2,4-disubstituted quinolines via silver-catalyzed [3 + 1 + 2] annulation of simple amines, alkyne esters and terminal alkynes. The versatile transformation might initiate with the facil
- Li, Yunlan,Zhang, Qiurui,Xu, Xuefeng,Zhang, Xu,Yang, Yurong,Yi, Wei
-
supporting information
p. 965 - 970
(2019/03/13)
-
- A Tf2O-Promoted Synthesis of Functionalized Quinolines from Ketoximes and Alkynes
-
A new general synthesis of quinolines was developed from ketoximes and alkynes in the presence of Tf2O. It offered the first direct synthesis of quinolines by using the nitrilium salts generated in situ from a Tf2O-promoted Beckmann rearrangement of ketoximes under very easy conditions. (Figure presented.).
- Zheng, Weiping,Yang, Weiguang,Luo, Dongping,Min, Lin,Wang, Xinyan,Hu, Yuefei
-
supporting information
p. 1995 - 1999
(2019/03/13)
-
- Manganese(ii)-catalysed dehydrogenative annulation involving C-C bond formation: highly regioselective synthesis of quinolines
-
An inexpensive nontoxic manganese(ii)-catalysed dehydrogenative annulation was developed for C-C bond formation. The reaction showed high selectivity and efficiency across a broad substrate scope. Remarkably simple conditions and the ability to conduct gram-scale synthesis underscore this method's utility. To demonstrate the potential of this approach, we tested the drug effects of compound 3n, which showed activity for blocking vascular development. The results of this study will be important for the treatment of eye diseases and tumors caused by vascular proliferation.
- Wang, Chengniu,Yang, Jinfei,Meng, Xiao,Sun, Yufeng,Man, Xuyan,Li, Jinxia,Sun, Fei
-
supporting information
p. 4474 - 4478
(2019/04/05)
-
- Electrophilic Cyclization of 2-Aminophenylprop-1-yn-3-ols into 3-Iodo-6-(aryldiazenyl)quinolines by Using a One-Pot Azo-Coupling and Iodocyclization Sequence
-
6-(Aryldiazenyl)-3-iodoquinolines were prepared from readily available 2-aminoaryl propargyl alcohols, aryldiazonium salts, and molecular iodine. This three-component one-pot process proceeded through sequential azo-coupling, regioselective iodocyclizatio
- Yaragorla, Srinivasarao,Pareek, Abhishek
-
supporting information
p. 1863 - 1871
(2018/05/09)
-
- Metal-free synthesis of quinolines by direct condensation of amides with alkynes: revelation of N-aryl nitrilium intermediates by 2D NMR techniques
-
Employing triflic anhydride/2-fluoropyridine as an activation system, the coupling reactions of secondary N-aryl amides with terminal alkynes yielded substituted quinolines in moderate to excellent yields. The reaction tolerated both electron-donating and electron-withdrawing groups at the benzamide moiety. Electron-rich aryl acetylenes served as excellent coupling partners, and aliphatic terminal alkynes such as cyclopropyl and conjugate vinyl acetylenes could also be used as reaction partners. By means of 2D NMR techniques (heteronuclear multiple bond correlation (HMBC), heteronuclear single quantum correlation (HSQC)), nitrilium ions were probed as reactive intermediates which are in contrast with that suggested by Movassaghi on the basis of in situ IR monitoring experiments. On the basis of these results, a plausible mechanism for the formation of quinolines was suggested.
- Ye, Jian-Liang,Zhu, Ya-Nan,Geng, Hui,Huang, Pei-Qiang
-
supporting information
p. 687 - 694
(2018/01/08)
-
- Acid-promoted iron-catalysed dehydrogenative [4 + 2] cycloaddition for the synthesis of quinolines under air
-
An acid-promoted iron-catalysed dehydrogenative [4 + 2] cycloaddition reaction was developed for the synthesis of quinolines using air as a terminal oxidant. Acetic acid was the best cocatalyst for the cycloaddition of N-alkyl anilines with alkenes or alk
- Yang, Jinfei,Meng, Xiao,Lu, Kai,Lu, Zhihao,Huang, Minliang,Wang, Chengniu,Sun, Fei
-
p. 31603 - 31607
(2018/09/25)
-
- Synthesis of Polysubstituted Quinolines from α-2-Aminoaryl Alcohols Via Nickel-Catalyzed Dehydrogenative Coupling
-
This study reports a nickel-catalyzed sustainable synthesis of polysubstituted quinolines from α-2-aminoaryl alcohols by a sequential dehydrogenation and condensation process that offers the advantages of a low catalyst loading and wide substrate scope. In contrast to earlier reported methods, this strategy allows the use of both primary as well as secondary α-2-aminoaryl alcohols in combination with either ketones or secondary alcohols for desired product formation. Using this methodology, 30 substituted quinoline derivatives were synthesized with up to 93% isolated yields.
- Das, Sanju,Maiti, Debabrata,De Sarkar, Suman
-
p. 2309 - 2316
(2018/02/23)
-
- Phosphine free Mn-complex catalysed dehydrogenative C-C and C-heteroatom bond formation: A sustainable approach to synthesize quinoxaline, pyrazine, benzothiazole and quinoline derivatives
-
Herein the first sustainable synthesis of quinoxalines, pyrazines and benzothiazoles catalysed by a phosphine free Mn(i) complex via acceptorless dehydrogenative coupling (ADC) is reported. This method is also applied successfully to synthesize quinolines via the dehydrogenation (removal of H2) and condensation (removal of H2O) reaction between 2-aminobenzyl alcohols and secondary alcohols.
- Das, Kalicharan,Mondal, Avijit,Srimani, Dipankar
-
supporting information
p. 10582 - 10585
(2018/09/25)
-
- Synthesis of multi-functionalized quinolines and 1,2-dihydroquinolines through FeCl3-mediated reactions of carbonyl compounds with 2-vinylanilines
-
A facile and efficient approach toward the synthesis of functionalized quinolines and 1,2-dihydroquinolines from carbonyl compounds and 2-vinylanilines is described. The protocol utilizes the nonhazardous and less expensive FeCl3 as catalyst wi
- Liu, Sha,Li, Gaoqiang,Xu, Feng
-
p. 888 - 892
(2018/07/25)
-
- Direct Assembly of 4-Substituted Quinolines with Vinyl Azides as a Dual Synthon via C=C and C-N Bond Cleavage
-
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
-
p. 4434 - 4438
(2018/08/07)
-
- Copper catalyzed oxidative coupling of ortho-vinylanilines with N-tosylhydrazones: Efficient synthesis of polysubstituted quinoline derivatives
-
Efficient and general copper catalyzed oxidative cyclization of ortho-vinylaniline has been accomplished employing N-tosylhydrazone as coupling partner. Various substituted quinoline derivatives of biological importance were achieved in good to excellent
- Reddy, Angula Chandra Shekar,Anbarasan, Pazhamalai
-
p. 102 - 108
(2018/05/22)
-
- Direct arylation for the synthesis of 2-arylquinolines from N-methoxyquinoline-1-ium tetrafluoroborate salts and arylboronic acids
-
A rapid and direct arylation reaction of N-methoxyquinoline-1-ium tetrafluoroborate derivatives and arylboronic acids with high regioselectivety at room temperature was discovered. The reaction shows exceptional functional group tolerance and broad substrate scope regarding both the quinoline derivatives and the arylboronic acids.
- Ren, Xiaoxiao,Han, Shuaijun,Gao, Xianying,Li, Jingya,Zou, Dapeng,Wu, Yangjie,Wu, Yusheng
-
p. 1065 - 1068
(2018/02/19)
-
- Br?nsted acid-catalyzed metal- and solvent-free quinoline synthesis from: N -alkyl anilines and alkynes or alkenes
-
Br?nsted acid-catalyzed cyclization reactions of N-alkyl anilines with alkynes or alkenes in the presence of oxygen gas as an oxidant under metal- and solvent-free conditions are described. Various quinoline derivatives are obtained in satisfactory to exc
- Ahmed, Waqar,Zhang, Sheng,Yu, Xiaoqiang,Yamamoto, Yoshinori,Bao, Ming
-
p. 261 - 265
(2018/01/17)
-
- Ligand promoted method for synthesizing polysubstituted quinoline under catalysis of cheap metal
-
The invention discloses a ligand promoted method for synthesizing polysubstituted quinoline under the catalysis of cheap metal. According to the method disclosed by the invention, a substituted arylamine compound and a substituted olefin compound are used
- -
-
Paragraph 0040; 0041; 0042; 0043; 0083
(2018/12/05)
-
- Preparation method of environment-friendly quinoline compound
-
The invention belongs to the technical field of medical and chemical intermediates and relevant chemistry, and provides a preparation method of an environment-friendly quinoline compound. The preparation method is characterized in that a N-substituted polyaniline derivative serving as a raw material reacts with a phenylacetylene or styrene derivative in the presence of a Bronsted acid catalyst andan oxidizing agent and in the absence of a solvent at the temperature of 80 to 160 DEG C for 24 hours to obtain the quinoline compound. The preparation method has the beneficial effects of easiness and convenience in operation, mild conditions, environmental friendliness, probability of realizing industrial production and higher yield of the quinoline compound. The quinoline compound synthesizedby the preparation method can be further functionalized to obtain various compounds, and is applied to the development and researches of natural products, function materials and fine chemicals.
- -
-
Paragraph 0036; 0037; 0038
(2018/04/03)
-
- A method for the synthesis of quinoline derivatives
-
The invention belongs to the technical field of organic synthesis and particularly relates to a synthesis method of quinoline derivatives. The synthesis method comprises the steps of sequentially adding aromatic amine, aldehyde and alcohol into a reaction
- -
-
Paragraph 0023-0026
(2017/08/23)
-
- Method for constructing quinoline compound by means of functionalization of organic antimony catalyzed C-H bond
-
The invention aims at developing a novel method for preparing a quinoline compound in a manner of high conversion rate and high yield from organic antimony frustrated lewis pair catalyst by means of C-H bond functionalization of imine and unsaturated hydr
- -
-
Paragraph 0024; 0025
(2017/08/29)
-
- A method for utilizing the aromatic amine, diketone synthesis of quinoline derivatives
-
The invention provides a method for synthesizing quinoline by aromatic amine and diketone and belongs to the technical field of synthesis of the quinoline. According to the method for synthesizing the quinoline by the aromatic amine and the diketone, unde
- -
-
Paragraph 0051; 0052
(2018/02/04)
-
- Utilization of CO2 as a C1 Building Block in a Tandem Asymmetric A3 Coupling-Carboxylative Cyclization Sequence to 2-Oxazolidinones
-
We report a tandem asymmetric aldehyde-alkyne-amine (A3) coupling-carboxylative cyclization sequence for the highly enantioselective synthesis of chiral N-aryl 2-oxazolidinones. This is a rare example of a multicatalyst-promoted asymmetric tand
- Gao, Xiao-Tong,Gan, Chen-Chen,Liu, Si-Yue,Zhou, Feng,Wu, Hai-Hong,Zhou, Jian
-
p. 8588 - 8593
(2017/12/08)
-
- A method for utilizing the aromatic amine, aromatic aldehyde, synthesized of quinoline derivatives
-
The invention provides a method for synthesizing a quinoline derivative by utilizing arylamine, aromatic aldehyde and ketone, and belongs to the technical field of the synthesis of the quinoline derivative. According to the method for synthesizing a quinoline derivative by utilizing arylamine, aromatic aldehyde and ketone, in the existence of silver trifluoromethanesulfonate and trifluoromethanesulfonic acid, the quinoline derivative is synthesized by virtue of the reaction of an arylamine compound, an aromatic aldehyde compound and ketone compound. A reaction general formula is as shown in the specification. Compared with the prior art, the method is not only applicable to a great amount of functional groups, but also is simple in operation, high in yield, single in product structure, convenient to separate and purify, safe, low in price and small in pollution.
- -
-
Paragraph 0027; 0028; 0029
(2018/01/11)
-
- Triple zirconocene/br?nsted acid/CuO cooperative and relay catalysis system for tandem Mannich addition/C-C formative cyclization/oxidation
-
A new triple cooperative and relay catalysis system featuring the Mannich addition followed by C-C construction and oxydehydrogenation is described. The zirconocene dichloride and trimellitic acid synergic catalysis triggered the Mannich addition and C-C bond construction reactions, while CuO allowed relay catalysis for oxydehydrogenation. This novel strategy demonstrated superior activity for the synthesis of substituted quinolines from commercially available anilines, aldehydes and ketones. The corresponding substituted quinolines were synthesized with 32 examples in 90-96% yields under mild reaction conditions. A novel zirconocene-Br?nsted acid complex, generated in situ and acting as an active catalyst, was validated from the mechanistic studies.
- Luo, Yanlong,Sun, Huaming,Zhang, Weiqiang,Wang, Xiu,Xu, Shan,Zhang, Guofang,Jian, Yajun,Gao, Ziwei
-
p. 28616 - 28625
(2017/07/10)
-
- Palladium-Catalyzed [5+1] Annulation of 2-(1-Arylvinyl) Anilines and α-Diazocarbonyl Compounds toward Multi-functionalized Quinolines
-
A palladium-catalyzed [5+1] annulation of 2-(1-arylvinyl) anilines and α-diazocarbonyl compounds has been developed, affording a series of multi-functionalized quinolines in moderate to good yields. This procedure proceeded with the sequential insertion o
- Zhu, Jiawei,Hu, Weiming,Sun, Song,Yu, Jin-Tao,Cheng, Jiang
-
p. 3725 - 3728
(2017/09/25)
-
- A medicine intermediate quinoline synthetic method of the compound
-
The invention provides a synthetic method of a quinoline compound as shown in the following formula (III). The method comprises the following steps: in an organic solvent, in existence of a catalyst, an accelerant and alkali, enabling a compound as shown in the formula (I) and a compound as shown in the formula (II) to carry out a reaction, so as to obtain a compound as shown in the formula (III), wherein R is H, C1-C6 alkyl, C1-C6 alkoxy or halogen. According to the method, the plurality of factors such as the catalyst, the accelerant, alkali and the organic solvent are selected, and the target product can be obtained at a high yield, so that the synthetic method can achieve a good industrial application value in the technical field of medical intermediate synthesis.
- -
-
Paragraph 0036; 0037; 0038; 0039'; 0040; 0041
(2017/08/25)
-
- Method for synthesizing substituted quinoline through Pd/Ti-catalyzed four-component carbonylation coupling reaction
-
The invention discloses a method for synthesizing substituted quinoline through a Pd/Ti-catalyzed four-component carbonylation coupling reaction. The method uses acetonitrile as a solvent and employs palladium acetate and phosphine ligand for high-efficie
- -
-
Paragraph 0013; 0014; 0015; 0016; 0017; 0018; 0045-50
(2017/04/13)
-
- Sustainable Synthesis of Quinolines and Pyrimidines Catalyzed by Manganese PNP Pincer Complexes
-
This study represents the first example an environmentally benign, sustainable, and practical synthesis of substituted quinolines and pyrimidines using combinations of 2-aminobenzyl alcohols and alcohols as well as benzamidine and two different alcohols,
- Mastalir, Matthias,Glatz, Mathias,Pittenauer, Ernst,Allmaier, Günter,Kirchner, Karl
-
supporting information
p. 15543 - 15546
(2016/12/16)
-
- Silver-catalyzed one-step synthesis of multiply substituted quinolines
-
A silver-catalyzed formation of C-C bond for the construction of a series of polysubstituted quinolines from arylamines, aldehydes, and ketones or arylamines and 1,3-diketones has been developed. The transformation is effective for a broad range of substrates, thus enabling the expansion of constituent architectures on the heterocyclic framework. This 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.
- Xu, Xuefeng,Liu, Wenmin,Wang, Zhiqiang,Feng, Yuquan,Yan, Yanlei,Zhang, Xu
-
supporting information
p. 226 - 229
(2015/12/31)
-