- Solvent-free and room temperature synthesis of 3-arylquinolines from different anilines and styrene oxide in the presence of Al2O3/MeSO3H
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A highly efficient, simple and environmentally friendly synthesis of 3-arylquinolines has been developed in the presence of Al2O3/ MeSO3H via one-pot reaction of anilines and styrene oxide. This methodology provides very rapid access to 3-arylquinolines in good to excellent yields under solvent-free conditions at room temperature in air.
- Sharghi, Hashem,Aberi, Mahdi,Khataminejad, Mohsen,Shiri, Pezhman
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- [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; 0135-0137
(2021/11/26)
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- Unexpected Annulation between 2-Aminobenzyl Alcohols and Benzaldehydes in the Presence of DMSO: Regioselective Synthesis of Substituted Quinolines
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An unexpected annulation among 2-aminobenzyl alcohols, benzaldehydes, and DMSO to quinolines has been disclosed. For the reported annulation between 2-aminobenzyl alcohols and benzaldehydes, the change of the solvent from toluene to DMSO led to the change of the product from the diheteroatomic cyclic benzoxazines to monoheteroatomic cyclic quinolines. This annulation can be used to synthesize regioselectively different substituted quinolines by the choice of different 2-amino alcohols, aldehydes, and sulfoxides as substrates. Interestingly, introducing substituent groups to the α-position of sulfoxides resulted in the interchange of the positions between benzaldehydes and sulfoxides in the product quinolines. On the basis of the control experiments and literatures, a plausible mechanism for this annulation was proposed.
- Yang, Tonglin,Nie, Zhi-Wen,Su, Miao-Dong,Li, Hui,Luo, Wei-Ping,Liu, Qiang,Guo, Can-Cheng
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p. 15228 - 15241
(2021/10/25)
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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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- Lewis acid catalyzed reactivity switch: Pseudo three-component annulation of nitrosoarenes and (epoxy)styrenes
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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.
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supporting information
p. 15032 - 15035
(2020/12/22)
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- Direct synthesis of 3-arylquinolines by a nano Pd-catalyzed regioselective C3-H arylation of quinolines
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3-Arylquinolines are biologically and medicinally very important compounds. Direct and regioselective C3-H arylation offers a straight forward methodology for their synthesis. In this work, we report their synthesis by a Pd nanoparticle catalyzed reaction
- Paul, Abhijit,Paul, Aditya,Yadav, Somnath
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supporting information
(2019/11/28)
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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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- Iodine monobromide catalysed regioselective synthesis of 3-arylquinolines from α-aminoacetophenones and: Trans -β-nitrostyrenes
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A simple and efficient method for regioselective synthesis of 3-arylquinolines is described from α-aminoacetophenones and trans-β-nitrostyrenes using 20 mol% iodine monobromide as a catalyst in acetonitrile solvent at 80 °C. The present method involves tandem reaction of α-aminoacetophenones and trans-β-nitrostyrenes, formation of two new C-C bonds and cleavage of one C-C bond in a single step. The salient features of the protocol are metal- and oxidant-free reaction conditions, broad substrate scope, and good yields.
- Gattu, Radhakrishna,Mondal, Santa,Ali, Saghir,Khan, Abu T.
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p. 347 - 353
(2019/01/10)
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- Lewis acid-catalyzed borono-minisci reactions of arylboronic acids and heterocycles
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A Lewis acid-catalyzed Minisci reaction between arylboronic acids and heterocycles has been developed. This radical-coupling reaction was demonstrated employing several different heterocycles as well as electron-rich arylboronic acids. Quinoline substrates afforded modest regioselectivity for substitution at the 4-position under the reaction conditions, in contrast to previously reported Br?nsted acid-mediated reactions with quinoline substrates that favored substitution at the 2-position.
- Biaco, Joyce L.,Jones, Savannah L.,Barker, Timothy J.
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p. 1687 - 1697
(2016/10/12)
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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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- Aerobic synthesis of substituted quinoline from aldehyde and aniline: Copper-catalyzed intermolecular C-H active and C-C formative cyclization
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An efficient method for the direct synthesis of substituted quinolines from anilines and aldehydes through C-H functionalization, C-C/C-N bond formation, and C-C bond cleavage has been developed. The method is simple and practical and employs air as an ox
- Yan, Rulong,Liu, Xingxing,Pan, Congming,Zhou, Xiaoqiang,Li, Xiaoni,Kang, Xing,Huang, Guosheng
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supporting information
p. 4876 - 4879
(2013/10/08)
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- Heteroatom-guided, palladium-catalyzed regioselective C-H functionalization in the synthesis of 3-arylquinolines
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A new approach for the regioselective functionalization of the C-3-position of quinolines is described. The method utilizes heteroatom guided regioselective C-3 palladation followed by arylation via transmetalation with aryl boronic acids to yield 3-aryl-N-acyl-1,2-dihydroquinolines. In a one-pot sequence, N-deacylation followed by aromatization leads to important 3-arylquinolines in good yields.
- Tiwari, Virendra Kumar,Pawar, Govind Goroba,Das, Riki,Adhikary, Amit,Kapur, Manmohan
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p. 3310 - 3313
(2013/07/26)
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- Palladium-catalyzed desulfitative arylation of 3-haloquinolines with arylsulfinates
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3-Haloquinolines can be functionalized via a palladium-catalyzed desulfitative coupling of arylsulfinates. This method tolerates substitution upon the aromatic ring and shows good selectivity toward variously substituted aromatic rings. Copyright
- Colomb, Julie,Billard, Thierry
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p. 1471 - 1474
(2013/04/24)
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- A facile and efficient one-pot synthesis of substituted quinolines from α-arylamino ketones under vilsmeier conditions
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An efficient: one-pot synthesis of substituted, quinolines from, α-arylamino ketones in the presence of PBr3 in DMF has been developed. This general protocol provides a novel and facile access to substituted quinolines by sequential Vilsmeier-H
- Wang, Yan,Xin, Xin,Liang, Yongjiu,Lin, Yingjie,Zhang, Rui,Dong, Dewen
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experimental part
p. 4165 - 4169
(2009/12/09)
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- PREPARATION OF 3-SUBSTITUTED QUINOLINES. II. PREPARATION AND CYCLODEHYDRATION OF α-ALKYL- AND α-PHENYL-β-ARYLAMINOACROLEIN DERIVATIVES
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α-Methyl-β-arylaminoacroleins were prepared by the hydrolysis of 2-methyl-1-arylamino-3-arylimino-1-propene derivatives. α-Ethyl- and α-phenyl-β-arylaminoacroleins were prepared by the reaction of arylamine and 2-substituted 1,1,3,3-tetraethoxypropane derivatives. 3-Methyl, 3-ethyl- and 3-phenylquinolines were obtained from α-methyl-, α-ethyl and α-phenyl-β-arylaminoacroleins on heating with aluminum bromide in good yields. α-Bromo-β-anilinoacrolein (9b) was prepared by the reaction of β-anilinoacrolein (6b) and N-bromosuccinimide.Reaction of 9b and aluminum bromide did not afford 3-bromoquinoline.
- Todoriki, Reiko,Ono, Machiko,Tamura, Shinzo
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p. 755 - 769
(2007/10/02)
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