9-氯-6,7-二甲氧基-2,3-二氢-1H-环戊二烯并[b]喹啉的合成
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摘要
报道一种9-氯-6,7-二甲氧基-2,3-二氢-1H-环戊二烯并[b]喹啉的简便制备方法。以2-氨基-4,5-二甲氧基苯甲酸和环戊酮为原料,在三氯氧磷作用下"一锅法"合成目标化合物9-氯-6,7-二甲氧基-2,3-二氢-1H-环戊二烯并[b]喹啉。产物结构经~1H NMR和ESI-MS确证。最佳反应条件为:环戊酮用量为1.5当量,120℃反应12 h,产物收率76.4%。按照最佳反应条件对于底物进行拓展,2-氨基-4,5-二甲氧基苯甲酸和环己酮反应得到9-氯-6,7-二甲氧基-1,2,3,4-四氢吖啶,收率64.2%。
9-Chloro-6,7-dimethoxy-2,3-dihydro-1H-cyclopenta[b]quinolonewas synthesized by an efficient and practical method from 2-amino-4,5-dimethoxybenzoic acid and cyclopentanone inthe presence ofphosphorus oxychloride by one pot.The structure of the product was confirmed by ~1H NMR and ESI-MS.The optimal reaction conditions were investigated.Target compound was obtained in a yield of 76.4% with 2-amino-4,5-dimethoxybenzoic acidas starting material,1.5 equvilent of cyclopentanone was used at 120℃ for 12 h in phosphorus oxychloride as solvent.The synthetic method wasused for synthesis of 9-chloro-6,7-dimethoxy-1,2,3,4-tetrahydroacridine in a yield of 64.2%.
9-Chloro-6,7-dimethoxy-2,3-dihydro-1H-cyclopenta[b]quinolonewas synthesized by an efficient and practical method from 2-amino-4,5-dimethoxybenzoic acid and cyclopentanone inthe presence ofphosphorus oxychloride by one pot.The structure of the product was confirmed by ~1H NMR and ESI-MS.The optimal reaction conditions were investigated.Target compound was obtained in a yield of 76.4% with 2-amino-4,5-dimethoxybenzoic acidas starting material,1.5 equvilent of cyclopentanone was used at 120℃ for 12 h in phosphorus oxychloride as solvent.The synthetic method wasused for synthesis of 9-chloro-6,7-dimethoxy-1,2,3,4-tetrahydroacridine in a yield of 64.2%.
引文
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[2]田俊锋,刘军,孙旭峰,等.具有生物活性的喹啉类化合物的研究进展[J].农药,2011,50(8):552-557.
[3]Lee C H,Lee H S.Growth inhibiting activity of quinaldic acid isolated from Ephedra pachyclada,against intestinal bacteria[J].Journal of the Korean Society for Applied Biological Chemistry,2009,52(4):331-335.
[4]Nielsen O H,Ahnfelt-R nne I,Elmgreen J.A Comparison of the Effect of Timegadine,Levamisole,and D Penicillamine on Human Neutrophil Metabolism of Endogenous Arachidonic Acid and Chemo taxis[J].Basic&Clinical Pharmacology&Toxicology,2010,62(5):322-325.
[5]Jarvis O D.Results of Treatment of Malaria by(a)Plasmoquine and Quinine,and(b)Atebrin,together with Some Observations on Malaria Convalescents[J].Land Degradation&Development,2015,18(1):26-31.
[6]Gjorup S,Poulsen H.Effects of probenecid,cinchophen and colchicine on the plasma concentration and renal excretion of oxypurine in patients with gout.[J].Basic&Clinical Pharmacology&Toxicology,2010,11(4):343-352.
[7]Yamadori Y,Oiso N,Hirao A,et al.Allergic contact dermatitis from dibucaine hydrochloride,chlorpheniramine maleate,and naphazoline hydrochloride in an over-the-counter topical antiseptic[J].Contact Dermatitis,2009,61(1):52-53.
[8]Rosenbaum T,Islas N D.Dequalinium[J].Journal of General Physiology,2003,121(121):37-47.
[9]闫建辉,姚国伟,杨丽娜,等.平行-连续法合成沙奎那韦[J].精细化工,2007,24(1):76-79.
[10]Kouznetsov V V,Mendez L Y V,Gomez C MM.Recent Progress in the Synthesis of Quinolines[J].Current Organic Chemistry,2005,36(16):141-161.
[11]Rosini M,Mancini F,Tarozzi A,et al.Design,synthesis,and biological evaluation of substituted 2,3-dihydro-1H-cyclopenta[b]quinolin-9-ylamine related compounds as fructose-1,6-bisphosphatase inhibitors[J].Bioorganic&Medicinal Chemistry,2006,14(23):7846-7853.
[12]Mikiciuk-Olasik E,Malawska B,Bajda M,et al.Synthesis and Biological Activity of New 2,3-dihydro-1H-cyclopenta[b]-quinoline Derivatives as Acetylcholinesterase Inhibitors[J].Letters in Drug Design&Discovery,2012,9(7):645-654.
[13]Pawe?Szymański,Alice Lázni ková,Milan Lázni ek,et al.2,3-Di hydro-1H-cyclopenta[b]quinoline Derivatives as Acetylcholineste rase Inhibitors-Synthesis,Radiolabeling and Biodistribution[J].International Journal of Molecular Sciences,2012,13(8):10067-10090.
[14]Neelima,Bhat B,Bhaduri A P.Novel syntheses of 3-cyano-3,4-di hydroquinolin-2(1H)-one and derivatives of 2,3-dicarbomethoxy-2-hydroxycyclopenta[b]quinoline[J].Journal of Heterocyclic Chemistry,2010,23(2):409-411.