3290-24-2Relevant articles and documents
Efficient synthesis of tetrahydroquinolines from the reaction of aldehyde, aniline, and alkene under the in situ redox of SnCl2 and FeCl 3
Guo, Qiaoxia,Teng, Weiling,Ren, Shenyong,Rao, Shasha,Wang, Yanqing,Chen, Liwei,Shen, Baojian,Takahashi, Tamotsu
, p. 1100 - 1105 (2014)
A highly efficient three-component Povarov reaction for the synthesis of tetrahydroquinoline derivatives was reported. The reaction of aldehyde, aniline, and alkene was carried out in the presence of Sn(IV), which was generated in situ from the redox reaction of SnCl2 and FeCl3, to afford tetrahydroquinoline derivatives in good to excellent yields. This discovery showed a sharp difference from the direct use of unstable SnCl4. Both aliphatic and aromatic aldehydes could be applied for the synthesis of the heterocycle in the reaction. The structure of the product 6-chloro-4-methyl-4- neopentyl-2-propyltetrahydroquinoline and 6-bromo-4-methyl-4-neopentyl-2- propyltetrahydroquinoline was confirmed by X-ray diffraction analysis.
THE TRANSITION METAL-CATALYZED N-ALKYLATION AND N-HETEROCYCLIZATION. A REDUCTIVE TRANSFORMATION OF NITROBENZENE INTO N,N-DIALKYLANILINE AND 2,3-SUBSTITUTED QUINOLINE USING ALDEHYDE AND CARBON MONOXIDE
Watanabe, Yoshihisa,Suzuki, Naoki,Shim, Sang Chul,Yamamoto, Michihiro,Mitsudo, Take-aki,Takegami, Yoshinobu
, p. 429 - 430 (1980)
The catalytic N-alkylation and N-heterocyclization of nitrobenzene occurs at 180 deg C under pressures of carbon monoxide (70 atm) in the presence of aldehyde and transition metal complexes to give 2,3-dialkyl quinoline and N,N-dialkylaniline in good yields.The product selectivity highly depends on the catalysts.
Multifunctional catalysis of heteropoly acid: One-pot synthesis of quinolines from nitroarene and various aldehydes in the presence of hydrazine
Hekmatshoar, Rahim,Sajadi, Sodeh,Sadjadi, Samaheh,Heravi, Majid M.,Beheshtiha, Yahya S.,Bamoharram, Fatemeh F.
, p. 1195 - 1198 (2008)
12-Molybdophosphoric acid catalyzed transfer hydrogenation of nitroarene by hydrazine in a homogeneous phase. This catalytic system was applicable to one-pot quinolines synthesis in the presence of various aldehydes in water. This method provides a new and efficient protocol in terms of mild reaction conditions, clean reaction profiles, small quantity of catalyst, and simple work-up procedure.
Ruthenium-catalyzed formal alkyl group transfer: Synthesis of quinolines from nitroarenes and alkylammonium halides
Cho, Chan Sik,Lee, Na Young,Kim, Tae-Jeong,Shim, Sang Chul
, p. 423 - 429 (2004)
Nitroarenes are reductively cyclized with an array of tetraalkylammonium halides and trialkylammonium chlorides in the presence of a catalytic amount of a ruthenium catalyst along with tin(II) chloride dihydrate at 180° to afford the corresponding quinolines in moderate to good yields. The addition of tin(lI) chloride dihydrate is necessary for the effective formation of quinolines and toluene is the solvent of choice. A reaction pathway involving initial reduction of nitroarenes to anilines and conversion of alkylammonium halides to alkylamines, alkyl group transfer from alkylamines to anilines to form an imine, dimerization of imine, and heteroannulation is proposed for this catalytic process.
On the mechanism of the chemiluminescent condensation of aniline with butyraldehyde catalyzed by LnCl3 ? 6H2O
Bulgakov,Kuleshov,Makhmutov,Dzhemilev
, p. 534 - 541 (2010)
The mechanism of the chemiluminescent condensation of aniline with butyraldehyde into 3-ethyl-2-propylquinoline catalyzed by LnCl3 ? 6H2O (Ln = Tb, Ho) is reported. A likely scheme of the catalytic condensation of aniline with butyraldehyde has been developed by simulation of separate steps of the reaction using chemiluminescence and photoluminescence methods and quantum-chemical calculations of the heats of these steps.
Method for preparing quinoline compound through oxidation and reduction integration (by machine translation)
-
Paragraph 0047-0048, (2020/02/17)
The method takes the aromatic nitro compound and the fatty alcohol as. the raw material and uses the aromatic nitro compound and the fatty, alcohol as the catalyst to, react under an inert atmosphere or under the, 150-200 °C atmosphere containing oxygen 2-12h, at the atmosphere, of oxygen containing, oxygen, to obtain the substituted, quinoline compound, and. the synthesis method can have important application in the aspect of quinoline compound. synthesis. (by machine translation)
Method for producing quinoline derivative through one-pot two-step method
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Paragraph 0043-0044, (2020/02/17)
The invention relates to a method for producing a quinoline derivative through a one-pot two-step method. According to the method, an aromatic nitro compound and fatty alcohol are used as raw materials, oxygen-containing molybdenum disulfide is used as a catalyst, firstly, under the conditions of 0.3-3.0-MPa hydrogen and 120-160 DEG C, a reaction is carried out for 2-10 h, the aromatic nitro compound is translated into an aromatic amine, then a reaction atmosphere is displaced, in an inert atmosphere or an oxygen-containing atmosphere, a reaction is carried out under the condition of 120-200 DEG C for 2-12 h, after the reaction is completed, a liquid-phase component is separated out, and is concentrated, and an obtained product is separated by a silica gel column to obtain a substituted qunoline compound. The synthesis method can have important application on the aspect of synthesis of quinoline compounds.
Reaction behaviour of arylamines with nitroalkenes in the presence of bismuth(iii) triflate: An easy access to 2,3-dialkylquinolines
Ali, Saghir,Gattu, Radhakrishna,Singh, Varun,Mondal, Santa,Khan, Abu T.,Dubey, Gurudutt,Bharatam
, p. 1785 - 1793 (2020/03/17)
We report the reaction behaviour of arylamines with nitroalkenes in the presence of bismuth(iii) triflate (10 mol%) and diacetoxyiodobenzene (10 mol%). We obtained 2,3-dialkylquinoline derivatives instead of the expected 3-alkylindole derivatives. The present reaction is an alternative approach for the synthesis of 2,3-dialkylquinoline derivatives under milder conditions. Furthermore, we establish the mechanistic pathway by theoretical calculations using Gaussian 09 software [B3LYP/6-311+G(d,p)], which shows that the conventional aza-Michael reaction is preferred over Michael addition. Aliphatic nitroalkenes behave in a different manner than aromatic nitroalkenes. An aza-Michael adduct gives rise to an imine by the elimination of water which may tautomerize to the corresponding enamine. The resulting imine and enamine intermediates react together to afford the desired quinoline derivatives. This protocol has the advantages of consecutive formation of one C-N and two C-C bonds, high regioselectivity, broad substrate-scope and good yields.
Mesoporous Aluminosilicates in the Synthesis of N-Heterocyclic Compounds
Agliullin, M. R.,Bikbaeva, V. R.,Bubennov, S. V.,Filippova, N. A.,Gataulin, A. R.,Grigor’eva, N. G.,Kostyleva, S. A.,Kutepov, B. I.,Narender, Nama
, p. 733 - 743 (2020/02/25)
Abstract: The catalytic properties of samples of amorphous mesoporous aluminosilicate ASM with different Si/Al molar ratios (40, 80, 160) were studied in the synthesis of practically important pyridines (by the interaction of С2–С5 alcohols with formaldehyde and ammonia, cyclocondensation of acetaldehyde and propionic aldehyde with ammonia), dialkylquinolines and alkyltetrahydroquinolines (by reaction of aniline with C3, C4 aldehydes) and alkyldihydroquinolines (by interaction of aniline with ketones, acetone and acetophenone). It is found that mesoporous aluminosilicate ASM sample with a molar ratio of Si/Al = 40, which has the highest acidity among the studied samples, exhibits the highest activity and selectivity in these reactions.
One-Pot Oxidative Synthesis of Substituted Quinolines from Alcohols and Arylamines Catalyzed by Fe(CrO2)2 in Water Medium
Makhmutov
, p. 1166 - 1172 (2018/10/24)
One-pot tandem synthesis was developed for substituted quinolines (in up to 97% yields) involving a selective catalytic oxidation of primary amines to aldehydes and their condensation with arylamines under the action of a dispersion of Fe(CrO2)2 and water solution of H2O2 at room temperature. The stage of catalytic oxidation of alcohols was accelerated by photoactivation. A presumable mechanism of the photoactivated tandem synthesis of 2-methylquinoline was suggested. Catalyst Fe(CrO2)2 was prepared by photochemical synthesis.
