- Bio-mediated oxidative resolution of racemic 2-substituted 1,2,3,4-tetrahydroquinolines
-
Whole cell of Pseudomonas monteilii ZMU-T01 strains mediated oxidative resolution of racemic 2-substituted 1,2,3,4-tetrahydroquinolines has been successfully described. A series of highly enantioselective 2-substituted 1,2,3,4-tetrahydroquinoline derivatives were obtained in up to 50% conversion and >99% ee.
- Qin, Lei,Zheng, Daijun,Cui, Baodong,Wan, Nanwei,Zhou, Xiaojian,Chen, Yongzheng
-
-
Read Online
- Preparation of 3-hydroxyquinolines from direct oxidation of dihydroquinolinium salts
-
A series of functionalized 3,4-dihydroquinolinium salts were prepared from the reaction of aryldiazonium salt with alkene in a nitrile solution. Further oxidation yielding either 3-hydroxyquinoline or quinoline products was investigated. A one-pot process from aryldiazonium salts, alkenes and nitriles leading to 3-hydroxyquinolines was also developed. Furthermore, an intramolecular trapping of an N-arylnitrilium ion with a vinyl group at the ortho position leading to 2-substituted quinolines was revealed.
- Ramanathan, Mani,Wan, Jing,Liu, Shiuh-Tzung
-
-
Read Online
- Expeditious preparation of 2-substituted quinolines
-
A library of 2-substituted quinolines was synthesized in solution from mixtures of Grignard reagents and a quinolinium salt. Grignard reagents were prepared in one pot, taking advantage of the entrainment method for their preparation from unreactive alkyl halides. Then mixtures of 2-alkylquinolines were readily accessible for biological tests or separated by centrifugal-partition chromatography (CPC) prior to the biological screening.
- Fakhfakh, Mohamed A.,Franck, Xavier,Fournet, Alain,Hocquemiller, Reynald,Figadère, Bruno
-
-
Read Online
- Straightforward synthesis of 2-propylquinolines under multicomponent conditions in fluorinated alcohols
-
The synthesis of 2-propylquinolines, a family of antileishmanial agents, is reported. Among the pathways explored, the 3-component Povarov reaction between butyraldehyde, aromatic amines and ethyl vinyl ether in trifluoroethanol (TFE), followed by an oxidation, offers a convenient entry to 2-propylquinolines with various substituents on positions 5-8.
- Venkateswarlu,Balaji,De, Kavita,Crousse, Benoit,Figadère, Bruno,Legros, Julien
-
-
Read Online
- Method for preparing quinoline derivative
-
The invention relates to a method for preparing a quinoline derivative. The method comprises the following steps: by taking aromatic amine compounds and fatty alcohol as raw materials and oxygen-containing molybdenum disulfide as a catalyst, performing a reaction for 2-12 hours in an inert atmosphere or an oxygen-containing atmosphere at the temperature of 120-200 DEG C, after the reaction is finished, separating liquid phase components, performing concentration, and performing separation through a silica gel column, so as to obtain a substituted quinoline compound. The synthetic method may have important application in the aspect of quinoline compound synthesis.
- -
-
Paragraph 0045-0046
(2020/02/17)
-
- Half-Sandwich Ruthenium Complexes for One-Pot Synthesis of Quinolines and Tetrahydroquinolines: Diverse Catalytic Activity in the Coupled Cyclization and Hydrogenation Process
-
Four types of half-sandwich ruthenium complexes with an N,O-coordinate mode based on hydroxyindanone-imine ligands have been prepared in good yields. These stable ruthenium complexes exhibited high activity in the catalytic synthesis of quinolines from the reactions of amino alcohols with different types of ketones or secondary alcohols under very mild conditions. Moreover, the methodology for the direct one-pot synthesis of tetrahydroquinoline derivatives from amino alcohols and ketones has been also developed on the basis of the continuous catalytic activity of this ruthenium catalyst in the selective hydrogenation of the obtained quinoline derivatives with a low catalyst loading. The corresponding products, quinolines and tetrahydroquinoline derivatives, were afforded in good to excellent yields. The efficient and diverse catalytic activity of these ruthenium complexes suggested their potential large-scale application. All of the ruthenium complexes were characterized by various spectroscopies to confirm their structures.
- Yun, Xue-Jing,Zhu, Jing-Wei,Jin, Yan,Deng, Wei,Yao, Zi-Jian
-
supporting information
p. 7841 - 7851
(2020/06/04)
-
- A Synthetic Route to Chiral Benzo-Fused N-Heterocycles via Sequential Intramolecular Hydroamination and Asymmetric Hydrogenation of Anilino-Alkynes
-
An efficient sequential intramolecular hydroamination/asymmetric hydrogenation reaction under catalysis of a single chiral ruthenium complex or a binary system consisting of achiral gold complex and chiral ruthenium complex has been reported. A diverse range of enantioenriched benzo-fused N-heterocycles, including 1,2,3,4-tetrahydroquinoline, indoline, and 2,3,4,5-tetrahydro-1H-benzo[b]azepine derivatives, were obtained from anilino-alkynes in high yields (up to 98%) with moderate to excellent enantioselectivities (up to 98% ee) under mild conditions. This protocol features good functional group tolerance and high atom economy. Furthermore, this catalytic protocol is applicable to gram-scale synthesis of a naturally occurring alkaloid, (-)-Angustureine.
- Xu, Cong,Feng, Yu,Li, Faju,Han, Jiahong,He, Yan-Mei,Fan, Qing-Hua
-
p. 3979 - 3990
(2019/11/14)
-
- Green synthesis of silver nanoparticles using green alga (Chlorella vulgaris) and its application for synthesis of quinolines derivatives
-
Nanoparticles have been used century ago but have regained their importance in recent years being simple, ecofriendly, pollutant free, nontoxic, low-cost approach, and due good atom economy. In this report, we have demonstrated the synthesis of silver nanoparticles using green algae (Chlorella vulgaris) which in turn was used for synthesis of biologically important quinolines. Algal extract was prepared and treated with silver nitrate solution for the synthesis of silver nanoparticles. Synthesized nanoparticles were characterized with the help of analytical tools like UV, FTIR, X-ray, and SEM and used as a catalyst for the synthesis of quinolines.
- Mahajan, Akhil,Arya, Anju,Chundawat, Tejpal Singh
-
supporting information
p. 1926 - 1937
(2019/05/17)
-
- Nickel-Catalyzed Alkylation of Ketone Enolates: Synthesis of Monoselective Linear Ketones
-
Herein we have developed a Ni-catalyzed protocol for the synthesis of linear ketones. Aryl, alkyl, and heteroaryl ketones as well as alcohols yielded the monoselective ketones in up to 90% yield. The catalytic protocol was successfully applied in to a gram-scale synthesis. For a practical utility, applications of a steroid derivative, oleyl alcohol, and naproxen alcohol were employed. Preliminary catalytic investigations involving the isolation of a Ni intermediate and defined Ni-H species as well as a series of deuterium-labeling experiments were performed.
- Das, Jagadish,Vellakkaran, Mari,Banerjee, Debasis
-
p. 769 - 779
(2019/01/24)
-
- Pd-Catalyzed Alkylation of (Iso)quinolines and Arenes: 2-Acylpyridine Compounds as Alkylation Reagents
-
The first Pd-catalyzed alkylation of (iso)quinolines and arenes is reported. The readily available and bench-stable 2-acylpyridine compounds were used as an alkylation reagent to form the structurally versatile alkylated (iso)quinolines and arenes. The method affords a convenient pathway for the introduction of alkyl groups into organic molecules.
- Wu, Qingsong,Han, Shuaijun,Ren, Xiaoxiao,Lu, Hongtao,Li, Jingya,Zou, Dapeng,Wu, Yangjie,Wu, Yusheng
-
supporting information
p. 6345 - 6348
(2018/10/20)
-
- Synthesis and structure of arene ruthenium(II) complexes: One-pot catalytic approach to synthesis of bioactive quinolines under mild conditions
-
Efficient catalytic one-step synthesis of substituted quinoline derivatives using newly synthesized Ru(II) half-sandwich complexes of the type [Ru(η6-p-cymene)Cl(L)] (L = pyrrole-2-aldehydehydrazones) under mild conditions is described. The synthesized complexes exhibit excellent catalytic activity towards the coupling of 2-amino alcohol with functionalized ketones and secondary alcohols in the optimal conditions and afforded the corresponding quinoline derivatives. The synthetic pathway proceeds with high atom efficiency via a sequence of acceptorless dehydrogenation and condensation steps. The maximum isolated yield of the product obtained was up to 97% using 0.3?mol% of catalyst loading for 5?h. These findings significantly advance the scope of the synthesis of bioactive heterocyclic compounds from readily available starting materials.
- Subramanian, Muthumari,Sundar, Saranya,Rengan, Ramesh
-
-
- 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)
-
- Deracemization of Phenyl-Substituted 2-Methyl-1,2,3,4-Tetrahydroquinolines by a Recombinant Monoamine Oxidase from Pseudomonas monteilii ZMU-T01
-
A monoamine oxidase (MAO5) from Pseudomonas monteilii ZMU-T01 was first heterologously expressed in Escherichia coli BL21(DE3) and then used as a biocatalyst for the deracemization of racemic 2-methyl-1,2,3,4-tetrahdroquinoline derivatives to yield the unreacted R enantiomer with up to >99 % ee. Sequence alignment revealed that MAO5 shared 14.7 % identity toward the well-studied monoamine oxidase (MAO-N).
- Deng, Guozhong,Wan, Nanwei,Qin, Lei,Cui, Baodong,An, Miao,Han, Wenyong,Chen, Yongzheng
-
p. 2374 - 2377
(2018/04/19)
-
- PdII-Catalyzed Oxidative Tandem aza-Wacker/Heck Cyclization for the Construction of Fused 5,6-Bicyclic N,O-Heterocycles
-
A PdII-catalyzed oxidative tandem cyclization was developed for the construction of fused 5,6-bicyclic N, O-heterocycles. This reaction was enabled by the combined use of a 3-methylpyridine ligand and pentafluorobenzoic acid additive. A range of heterocyclic products with different substituents could be prepared in moderate to good yields via this methodology. Several transformations, including a scaled-up preparation of product 2 a, were also carried out showing the good applicability of our methodology.
- Ye, Chenghao,Kou, Xuezhen,Xia, Jingzhao,Yang, Guoqiang,Kong, Li,Wei, Quhao,Zhang, Wanbin
-
supporting information
p. 1897 - 1901
(2018/07/31)
-
- Nickel-Catalyzed Hydrogenolysis and Conjugate Addition of 2-(Hydroxymethyl)pyridines via Organozinc Intermediates
-
2-Hydroxymethylpyridines undergo nickel-catalyzed hydrogenolysis upon activation with a chlorophosphate. Reactions employ diethylzinc and are proposed to proceed through secondary benzylzinc reagents. Quenching with deuteromethanol provides straightforward incorporation of a deuterium label in the benzylic position. Intramolecular conjugate additions with α,β-unsaturated esters are also demonstrated and support the intermediacy of a benzylzinc complex.
- Hanna, Luke E.,Harris, Michael R.,Domon, Kenji,Jarvo, Elizabeth R.
-
p. 6304 - 6307
(2017/12/08)
-
- Iridium-catalysed hydrosilylation of cyclopropanes: Via regioselective carbon-carbon bond cleavage
-
While cyclopropanes have been explored as synthetically valuable building blocks, their transformation without conjugated substituents or directly substituted heteroatoms remains challenging. The current study describes the iridium-catalysed ring-opening hydrosilylation of cyclopropanes. A nitrogen-based directing group was found to control the reactivity of iridium active species as well as the regiochemistry of carbon-carbon bond cleavage and hydrosilylation.
- Murai, Masahito,Nishiyama, Atsushi,Nishinaka, Naoki,Morita, Haruka,Takai, Kazuhiko
-
supporting information
p. 9281 - 9284
(2017/08/21)
-
- Isolation and Characterization of Regioisomers of Pyrazole-Based Palladacycles and Their Use in α-Alkylation of Ketones Using Alcohols
-
Regioisomers of 3,5-diphenyl-1-(4-(trifluoromethyl)phenyl)-1H-pyrazole-based palladacycles (1 and 2) were synthesized by the aromatic C-H bond activation of N/3-aryl ring. The application of these regioisomers as catalysts to enable the formation of α-alkylated ketones or quinolines with alcohols using a hydrogen borrowing process is evaluated. Experimental results reveal that palladacycle 2 is superior over palladacycle 1 to catalyze the reaction under similar reaction conditions. The reaction mechanisms for the palladacycles 1 and 2 catalyzed α-alkylation of acetophenone were studied using density functional theoretical (DFT) methods. The DFT studies indicate that palladacycle 2 has an energy barrier lower than that of palladacycle 1 for the alkylation reaction, consistent with the better catalytic activity of palladacycle 2 seen in the experiments. The palladacycle-phosphine system was found to tolerate a wide range of functional groups and serves as an efficient protocol for the synthesis of α-alkylated products under solvent-free conditions. In addition, the synthetic protocol was successfully applied to prepare donepezil, a drug for Alzheimer's disease, from simple starting materials.
- Mamidala, Ramesh,Samser, Shaikh,Sharma, Nishant,Lourderaj, Upakarasamy,Venkatasubbaiah, Krishnan
-
supporting information
p. 3343 - 3351
(2017/09/18)
-
- Asymmetric combinational “metal-biocatalytic system”: One approach to chiral 2-subsituted-tetrahydroquinoline-4-ols towards two-step one-pot processes in aqueous media
-
A novel asymmetric “metal-biocatalytic system”, involving Rh-catalyzed asymmetric transfer hydrogenation and whole cell mediated asymmetric hydroxylation in aqueous buffer, has been achieved. The methodology gives access to 2-subsituted-tetrahydroquinoline-4-ols bearing two stereocenters from 2-subsituted-quinolines in moderate to excellent results (up to 47% yield, 99:1 dr, and >99% ee).
- Wang, Juxiang,Li, Ke,Zhou, Xiaojian,Han, Wenyong,Wan, Nanwei,Cui, Baodong,Wang, Huihui,Yuan, Weicheng,Chen, Yongzheng
-
supporting information
p. 2252 - 2254
(2017/05/17)
-
- Synthesis of Quinolines via Iron-Catalyzed Redox Condensation of Alcohols with 2-Nitrobenzyl Methyl Ether/2-Nitrobenzyl Alcohols
-
An iron-catalyzed redox condensation of 2-nitrobenzyl alcohols, formic acid, and alcohols has been developed, which affords substituted quinolines with carbon dioxide and water as the only side products. With the use of formic acid as a redox moderator to fill the electron gap of the global redox condensation process, the reaction goes smoothly with a smaller amount of alcohol in comparison to previous reports (i.e. 1.2 equiv versus 3.3-4 equiv). The reaction goes equally well when 2-nitrobenzyl methyl ether was used instead of 2-nitrobenzyl alcohol under otherwise identical conditions, shedding a new light on the study of this quinoline synthetic method.
- Wang, Qi,Wang, Meirong,Li, Hui-Jing,Zhu, Shuai,Liu, Ying,Wu, Yan-Chao
-
p. 3985 - 3995
(2016/11/11)
-
- Unsupported nanoporous gold catalyst for highly selective hydrogenation of quinolines
-
For the first time, the highly efficient and regioselective hydrogenation of quinoline derivatives to 1,2,3,4-tetrahydroquinolines using unsupported nanoporous gold (AuNPore) as a catalyst and organosilane with water as a hydrogen source is reported. The AuNPore catalyst can be readily recovered and reused without any loss of catalytic activity.
- Yan, Mei,Jin, Tienan,Chen, Qiang,Ho, Hon Eong,Fujita, Takeshi,Chen, Lu-Yang,Bao, Ming,Chen, Ming-Wei,Asao, Naoki,Yamamoto, Yoshinori
-
supporting information
p. 1484 - 1487
(2013/06/26)
-
- Cooperative catalysis with metal and secondary amine: Synthesis of 2-substituted quinolines via addition/cycloisomerization cascade
-
A cooperative catalytic system, consisting of CuI and pyrrolidine, has been developed for an efficient synthesis of 2-substituted quinolines. A combination of both the catalysts is necessary; the use of either catalyst alone does not give the product.
- Patil, Nitin T.,Raut, Vivek S.
-
supporting information; experimental part
p. 6961 - 6964
(2010/11/19)
-
- Concerning the mechanism of the Friedlaender quinoline synthesis
-
Detailed experiments regarding the mechanism of the Friedlaender synthesis of quinolines from o-amino-benzaldehydes and simple aldehydes or ketones are described. Under the basic or acidic conditions commonly used in this reaction, it is concluded that the first step involves a slow intermolecular aldol condensation of the aldehyde or ketone with the o-aminobenzaldehyde. The aldol adduct 5 generated in this manner then undergoes very rapid cyclization to 4, which subsequently loses water to produce the quinoline derivative 8. Both 5 and 4 are too short lived to be detectable (TLC), even when deliberately generated by other means. It is also shown that E-enones corresponding to 6, i.e., the aldol dehydration product, are converted into quinolines (e.g., 21a and 21b from 17a and 17b) under basic or acidic conditions. Such enones are not detected as intermediates in the base-induced Friedlaender synthesis, even though certain congeners (17b) would be easily observable. Under acidic conditions these enones are too short lived to be detectable. Schiff bases derived from 2-aminobenzaldehyde (18a) and aldehydes or ketones can be generated under special conditions, but they show reactivity patterns different from those seen in the usual Friedlaender condensations. Thus, the ytterbium-triflate-catalyzed reaction of aldehydes with 18a at room temperature in toluene generates the E-Schiff bases (33, R1 = H), from which isomeric mixtures of tetrahydroquinoline derivatives 26 are formed exclusively. At higher temperatures, the E-Schiff bases 33 are isomerized to the Z-Schiff bases 34, from which the 3-substituted quinoline derivatives 24 are formed as the major products under appropriate conditions. Also, the ytterbium-triflate-catalyzed reaction of 18a with the pyrrolidine enamines of the methyl-n-alkylketones 38a,b produces mixtures in which the 2-monosubstituted kinetic products 37b,d predominate over the 2,3-disubstituted thermodynamic products 21c,e by a factor of 4:1 to 5:1. These results are opposite to those observed under the usual basic or acidic Friedlaender reactions with methyl-n-alkylketones, where the thermodynamic products are usually strongly favored. The unusual kinetic:thermodynamic product ratios observed with 38a,b are ascribed to the generation and rapid cyclization of mixtures of the Schiff bases 35 and 36, in which the kinetic isomer 35 is highly predominant.
- Muchowski, Joseph M.,Maddox, Michael L.
-
p. 461 - 478
(2007/10/03)
-
- Synthesis of 10-hydroxy-3-methyl-1H-pyrano[4,3-b]-quinoline derivatives
-
Heating of 4-arylamino-3-ethoxycarbonyl-6-methyl-2H-pyran-2-one derivatives (3), which were obtained from the reaction between 4-chloro-3-ethoxycarbonyl-6-methyl-2H-pyran-2-one (2) and anilines, in PPA gave corresponding 10-hydroxy-3-methylpyrano[4,3-b]qu
- Morone, Mieko,Sato, Atsuko,Azuma, Yutaka
-
p. 2241 - 2249
(2007/10/03)
-
- Synthesis and biological evaluation of substituted quinolines: Potential treatment of protozoal and retroviral co-infections
-
We report the synthesis of substituted quinolines and their in vitro biological evaluation against the causal agents of cutaneous leishmaniasis, visceral leishmaniasis, African trypanosomiasis and Chagas' disease. Furthermore, several quinolines have also been tested for their anti-retroviral activity in HIV-1 infected cells. The structure-activity relationships of these new synthetic compounds are discussed and emphasis was placed on the treatment of leishmania/HIV co-infections.
- Fakhfakh, Mohammed A.,Fournet, Alain,Prina, Eric,Mouscadet, Jean-Francois,Franck, Xavier,Hocquemiller, Reynald,Figadere, Bruno
-
p. 5013 - 5023
(2007/10/03)
-
- Indium metal as a reducing agent in organic synthesis
-
The low first ionisation potential (5.8 eV) of indium coupled with its stability towards air and water, suggest that this metallic element should be a useful reducing agent for organic substrates. The use of indium metal for the reduction of C=N bonds in imines, the heterocyclic ring in benzo-fused nitrogen heterocycles, of oximes, nitro compounds and conjugated alkenes and the removal of 4-nitrobenzyl protecting groups is described. Thus the heterocyclic ring in quinolines, isoquinolines and quinoxalines is selectively reduced using indium metal in aqueous ethanolic ammonium chloride. Treatment of a range of aromatic nitro compounds under similar conditions results in selective reduction of the nitro groups; ester, nitrile, amide and halide substituents are unaffected. Likewise indium in aqueous ethanolic ammonium chloride is an effective method for the deprotection of 4-nitrobenzyl ethers and esters. Indium is also an effective reducing agent under non-aqueous conditions and α-oximino carbonyl compounds can be selectively reduced to the corresponding N-protected amine with indium powder, acetic acid in THF in the presence of acetic anhydride or di-tert-butyl dicarbonate. Conjugated alkenes are also reduced by indium in THF-acetic acid.
- Pitts,Harrison,Moody
-
p. 955 - 977
(2007/10/03)
-
- Diels-Alder reaction of 1,2,3-benzotriazine with enamine: Application to the synthesis of alkaloids, 2-propylquinoline and 2-pentylquinoline
-
The Diels-Alder reaction of 1,2,3-benzotriazine with several pyrrolidine enamines of carbonyl compounds was carried out in chloroform in the presence of zinc bromide to afford 2- or 3-mono-, or 2,3-disubstituted quinolines. This method was applied to the synthesis of the alkaloids, 2-propylquinoline and 2-pentylquinoline.
- Koyama, Junko,Toyokuni, Izumi,Tagahara, Kiyoshi
-
p. 332 - 334
(2007/10/03)
-
- Syntheses of quinolines, dihydro- and tetrahydroquinolines via ortho-quinone methide imine intermediate
-
A general process for ortho-specific hydroxyalkylation of secondary anilines via N-alkylanilinochlorophenylboranes has been developed. Pyrolysis of the resulting ortho-aminobenzyl alcohols generated the corresponding ortho-quinone methide imines, which can participate in an electrocyclic reaction to yield 2-substituted-1,2-dihydroquinolines. The resulting dihydroquinolines can be converted readily to a variety of 2-substituted quinolines. Intramolecular trapping of the ortho-quinone methide imines with an olefin via a [2 + 4] cycloaddition reaction leads to the syntheses of various polycyclic tetrahydroquinolines.
- Wiebe, Jennifer M.,Caille, Alain S.,Trimble, Laird,Lau, Cheuk K.
-
p. 11705 - 11724
(2007/10/03)
-
- Palladium-Assisted N-Alkylation of Indoles: Attempted Application to Polycyclization
-
The palladium(II) complexes of the olefins ethene, propene, and 1-hexene reacted with 1-lithioindole to produce N-alkylated indoles exclusively.Attempts to perform this N-alkylation intramoleculary (to form tricyclic material from 2-allylskatole) failed.Anilines with dienic side chains in the 2-position were subjected to Pd(II)-assisted cyclization conditions in attempts to induce polycyclization.However, only monocyclization was observed.
- Hegedus, Louis S.,Winton, Peter M.,Varaprath Sudarsanan
-
p. 2215 - 2221
(2007/10/02)
-