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第 8 期 卢 粤，等: 深共熔溶剂法合成喹啉衍生物 ·1431·

semecarpifolia[J]. Planta Med, 2002, 68(9): 790-793.
[9] Narwal S, Kumar S, Verma P K. Synthesis and therapeutic potential
of quinoline derivatives[J]. Res Chem Intermediat, 2017, 43(5):
2765-2798.
[10] Zhang X, Campo M A, Yao T, et al. Synthesis of substituted
quinolines by electrophilic cyclization of N-(2-alkynyl) anilines[J].
Org Lett, 2005, 7(5): 763-766.
[11] Kouznetsov V V, Méndez L Y V, Gómez C M M. Recent progress in
the synthesis of quinolines[J]. Curr Org Chem, 2005, 9(2): 141-161.
[12] Yadav J S, Rao P P, Sreenu D, et al. Sulfamic acid: An efficient,

cost-effective and recyclable solid acid catalyst for the Friedlander
图 4 DES 的重复利用 quinoline synthesis[J]. Tetrahedron Lett, 2005, 46(42): 7249-7253.
Fig. 4 Recycle of DES [13] Sloop J C. Quinoline formation via a modified combes reaction:

Examination of kinetics, substituent effects, and mechanistic
3 结论 pathways[J]. J Phys Org Chem, 2009, 22(2): 110-117.
[14] Yang D Q, Lü F, Li W H, et al. Synthesis of indenoquinoline
本文建立了一种合成喹啉类化合物的绿色高效 derivatives via Friedländer condensation reaction[J]. Chinese J Org
方法，通过优化 DES 种类、有机溶剂和反应温度等 Chem, 2004, 24(11): 1465-1468.
[15] Fehnel E A. Friedländer syntheses with O-aminoaryl ketones. I.
影响因素，确立了反应的最佳条件（在 0.5 mL 氯化
acid-catalyzed condensations of o-aminobenzophenone with
胆碱/草酸 DES 中，加入 0.3 mmol 2-氨基芳基酮和
ketones1[J]. J Org Chem, 1966, 31(9): 2899-2902.
0.36 mmol α-亚甲基酮，搅拌下于 80 ℃油浴中反应 [16] McNaughton B R, Miller B L. A mild and efficient one-step synthesis
1 h），在最优条件下拓展了 11 对底物，取得了最高 of quinolines[J]. Org Lett, 2003, 5(23): 4257-4259.
94%的产率。该方法不需要添加有机溶剂和其它催 [17] Arumugam P, Karthikeyan G, Atchudan R, et al. A simple, efficient
and solvent-free protocol for the Friedländer synthesis of quinolines
化剂，而且 DES 可重复利用，符合绿色化学理念，
by using SnCl 2· 2H 2O[J]. Chem Lett, 2005, 34(3): 314-315.
对推动有机合成的绿色化具有积极意义。
[18] Karthikeyan G, Perumal P T. A mild, efficient and improved protocol
for the Friedlaender synthesis of quinolines using Lewis acidic ionic
参考文献：
liquid[J]. J Heterocyclic Chem, 2005, 36(20): 1039-1041.
[1] Michael J P. Quinoline, quinazoline and acridone alkaloids[J]. Nat [19] Huddleston J G, Willauer H D, Swatloski R P, et al. Room
Prod Rep, 2008, 25(1): 166-187. temperature ionic liquids as novel media for ‘clean’ liquid–liquid
[2] Stork G, Niu D, Fujimoto A, et al. The first stereoselective total extraction[J]. Chem Commun, 1998 (16): 1765-1766.
synthesis of quinine[J]. J Am Chem Soc, 2001, 123(14): 3239-3242. [20] Deetlefs M, Seddon K R. Ionic liquids: Fact and fiction[J]. Chim
[3] Lam K H, Lee K K H, Gambari R, et al. Anti-tumour and Oggi, 2006, 24(2): 16-23.
pharmacokinetics study of 2-formyl-8-hydroxy-quinolinium chloride [21] Deetlefs M, Seddon K R. Assessing the greenness of some typical
as galipea longiflora alkaloid analogue[J]. Phytomedicine, 2014, laboratory ionic liquid preparations[J]. Green Chem, 2010, 12(1):
21(6): 877-882. 17-30.
[4] Talamas F X, Abbot S C, Anand S, et al. Discovery of [22] Scammells P J, Scott J L, Singer R D. Ionic liquids: The neglected
N-[4-[6-tert-butyl-5-methoxy-8-(6-methoxy-2-oxo-1 H-pyridin-3-yl)- issues[J]. Aust J Chem, 2005, 36(31): 155-169.
3-quinolyl] phenyl] methanesulfonamide (RG7109), a potent [23] Lu chao (鲁超), Su Erzheng (苏二正), Wei dongzhi (魏东芝). The
inhibitor of the hepatitis C virus NS5B polymerase[J]. J Med Chem, applications of deep eutectic solvents in biocatalysis[J]. Journal of
2013, 57(5): 1914-1931. Molecular Catalysis (分子催化), 2015(4): 390-401.
[5] Lam K H, Gambari R, Lee K K H, et al. Preparation of [24] Chen Xiaofen (陈小芬), Peng Yanqing (彭延庆). Application of deep
8-hydroxyquinoline derivatives as potential antibiotics against eutectic solvents in green synthesis and combinatorial chemistry[J].
staphylococcus aureus[J]. Bioorg Med Chem Lett, 2014, 24(1): Shanghai Chemical Industry (上海化工), 2008, 33(10): 10-13.
367-370. [25] Zhang Yingying (张盈盈), Lu Xiaohua (陆小华), Feng Xin (冯新),
[6] Vandekerckhove S, Tran H G, Desmet T, et al. Evaluation of et al. Properties and applications of choline-based deep eutectic
(4-aminobutyloxy) quinolines as a novel class of antifungal agents[J]. solvents[J]. Progress In Chemistry (化学进展), 2013, 25(6): 881-892.
Bioorg Med Chem Lett, 2013, 23(16): 4641-4643. [26] Shahabi D, Tavakol H. One-pot synthesis of quinoline derivatives
[7] Ratheesh M, Sindhu G, Helen A. Anti-inflammatory effect of using choline chloride/tin (II) chloride deep eutectic solvent as a
quinoline alkaloid skimmianine isolated from ruta graveolens L[J]. green catalyst[J]. J Mol Liq, 2016, 220: 324-328.
Inflamm Res, 2013, 62(4): 367-376. [27] Enugala R, Nuvvula S, Kotra V, et al. ChemInform abstract: Green
[8] Chen J J, Chang Y L, Teng C M, et al. Quinoline alkaloids and approach for the efficient synthesis of quinolines promoted by citric
anti-platelet aggregation constituents from the leaves of melicope acid[J]. Heterocycles, 2009, 40(7): 2523-2533.