一种查耳酮类化合物的合成方法
A method for the synthesis of chalcones
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摘要: 建立一种以取代苯乙酮和取代苯甲醛为原料,采用多聚磷酸/浓硫酸体系催化合成查耳酮类化合物的方法,并对反应条件进行优化。结果表明,最优反应条件为多聚磷酸5 equiv.、浓硫酸20 equiv.,1,4-二氧六环作溶剂,90 ℃氮气保护下反应2 h。在优化的反应条件下,以较好的得率合成了12个查耳酮类化合物。所有化合物结构通过IR、HRMS、1H NMR和13C NMR进行表征。Abstract: In this paper,a new method for catalytic synthesis of chalcones from substituted acetophenone and substituted benzaldehyde in polyphosphoric acid/concentrated sulfuric acid system was proposed,and the reaction conditions were optimized. The results showed that the optimized reaction conditions were determined as polyphosphoric acid of 5 equiv. and concentrated sulfuric acid of 20 equiv.,with 1,4-dioxane as solvent at 90 °C for 2 h under nitrogen protection. Twelve chalcones were synthesized with good yield. All target compounds were characterized by IR,HRMS,1H NMR and 13C NMR.
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Keywords:
- chalcones /
- condensation /
- polyphosphoric acid/H2SO4 /
- acetophenones /
- benzaldehydes /
- synthesis
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[1] .J Nat Prod,2015,78(10):2481?2487. [2] Liu XF,Shi DH.Research progress in the synthesis of chalcone[J].Appl Chem Ind(应用化工),2012,38(8):1210?1213,1219. [3] Kulkarni P.Calcium oxide catalyzed synthesis of chalcone under microwave condition[J].Curr Microw Chem,2015,2(2):144?149. [4] Duan HC,Jiang H,Gong H.Green synthesis of chalcone derivatives[J].China Pharm(中国药业),2006,15(15):30?31. [5] Zhuang C,Zhang W,Sheng C,et al.Chalcone:a privileged structure in medicinal chemistry[J].Chem Rev,2017,117(12):7762?7810. [6] Miyaura N,Suzuki A.Stereoselective synthesis of arylated(E)-alkenes by the reaction of alk-1-enylboranes with aryl halides in the presence of palladium catalyst[J].J Chem Soc Chem Commun,1979,19(19):135?152. [7] Heck RF,Nolley JP.Palladium-catalyzed vinylic hydrogen substitution reactions with aryl,benzyl,and styryl halides[J].J Org Chem,1972,37(14):2320?2322. [8] Kumar A,Sharma S,Tripathi VD,et al.Synthesis of chalcones and flavanones using Julia-Kocienski olefination[J].Tetrahedron,2010,66(48):9445?9449. [9] Bestmann HJ,Arnason B.Reaktionen mit phosphin-alkylenen,II.C-acylierung von phosphin-alkylenen.ein neuer weg zur synthese von ketonen[J].Chem Ber,1962,95(6):1513?1527. [10] Tripathi S,Kapoor R,Yadav LDS.Visible light activated radical denitrative benzoylation of β-nitrostyrenes:a photocatalytic approach to chalcones[J].Adv Synth Catal,2018,360(7):1407?1413. [11] Parveen I,Khan D,Ahmed N.Regioselective hydrodehalogenation of aromatic α- and β-halo carbonyl compounds by CuI in isopropanol[J].Eur J Org Chem,2019,2019(4):759?764. [12] Mellado M,Madrid A,Reyna M,et al.Synthesis of chalcones with antiproliferative activity on the SH-SY5Y neuroblastoma cell line:quantitative structure-activity relationship models[J].Med Chem Res,2018,27(11/12):2414?2425. [13] Wu YF,Zhou GL,Meng QW,et al.Visible light-induced aerobic epoxidation of α,β-unsaturated ketones mediated by amidines[J].J Org Chem,2018,83(21):13051?13062. [14] Thomson CJ,Barber DM,Dioxn DJ.One-pot catalytic enantioselective synthesis of 2-pyrazolines[J].J Angew Chem Int Edit,2019,58(8):2469?2473. [15] Wang C,Huang LY,Wang FZ,et al.Highly efficient synthesis of aryl ketones by PEPPSI-palladium catalyzed acylative Suzuki coupling of amides with diarylborinic acids[J].Tetrahedron Lett,2018,59(23):2299?2301. [16] Zhang ML,Xi J,Ruzi R,et al.Domino-fluorination-protodefluorination enables decarboxylative cross-coupling of α-oxocarboxylic acids with styrene via photoredox catalysis[J].J Org Chem,2017,82(18):9305?9311. [17] Abdel-Halim M,Keeton AB,Gurpinar E,et al.Trisubstituted and tetrasubstituted pyrazolines as a novel class of cell-growth inhibitors in tumor cells with wild type p53[J].Bioorg Med Chem,2013,21(23):7343?7356. [18] Ahmed MG,Romman U,Ahmed SM,et al.Synthesis and correlation of spectral properties of some substituted 1,3-diphenyl-2-propen-1-ones[J].Bangladesh J Sci Ind Res,1970,42(1):45?52. -
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