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Synthesis and antibacterial activity of ethyl 2-amino-6-methyl-5-oxo-4-aryl-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carboxylate 被引量：3

Synthesis and antibacterial activity of ethyl 2-amino-6-methyl-5-oxo-4-aryl-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carboxylate
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摘要 The three-component reaction of 4-hydroxy-l-methyl-2（1H）-quinolinone, aromatic aldehydes and ethyl cyanoacetate was carried out in the presence of a catalytic amount of 4-dimethyl aminopyridine （DMAP） in aqueous ethanol. The reactions result in the formation of pyranoquinoline derivatives in excellent yields. Antibacterial activity has been evaluated against Gram positive and Gram negative bacteria for some of the synthesized compounds. The results indicated that these compounds are moderately effective against bacterial growth and their effectiveness is highest against Pseudomonas aeruginosa. The three-component reaction of 4-hydroxy-l-methyl-2（1H）-quinolinone, aromatic aldehydes and ethyl cyanoacetate was carried out in the presence of a catalytic amount of 4-dimethyl aminopyridine （DMAP） in aqueous ethanol. The reactions result in the formation of pyranoquinoline derivatives in excellent yields. Antibacterial activity has been evaluated against Gram positive and Gram negative bacteria for some of the synthesized compounds. The results indicated that these compounds are moderately effective against bacterial growth and their effectiveness is highest against Pseudomonas aeruginosa.
作者 Sakineh Asghari Samaneh Ramezani Mojtaba Mohseni
机构地区 Department of Organic Chemistry Nano and Biotechnology Research Group Department of Microbiology
出处 《Chinese Chemical Letters》 SCIE CAS CSCD 2014年第3期431-434,共4页 中国化学快报（英文版）
基金 supported by the Research Council of the University of Mazandaran in Iran
关键词 Three-component reactionPyranoquinoline4-Dimethyl aminopyridine （DMAP）Antibacterial activity Three-component reactionPyranoquinoline4-Dimethyl aminopyridine （DMAP）Antibacterial activity
分类号 O621.2 [理学—有机化学] TQ460.1 [化学工程—制药化工]
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参考文献47

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二级参考文献252

共引文献19

同被引文献19

  • 1Sakineh Asghari,Samaneh Ramezani,Mojtaba Mohseni.Synthesis and antibacterial activity of ethyl 2-amino-6-methyl-5-oxo-4-aryl-5,6-dihydro-4 H -pyrano[3,2-c]quinoline-3-carboxylate[J].Chinese Chemical Letters.2013
  • 2Sakineh Asghari,Ahmad Khabbazi Habibi.One pot three-component regioselective and diastereoselective synthesis of halogenated pyrido[2,1- b ][1,3]oxazines[J].Tetrahedron.2012(43)
  • 3Abbas Ali Esmaeili,Hamid Vesalipoor,Rahele Hosseinabadi,Alireza Fakhari Zavareh,Mohammad Ali Naseri,Ebrahim Ghiamati.An efficient diastereoselective synthesis of spiro pyrido[2,1- b ][1,3]oxazines via a novel pyridine-based three-component reaction[J].Tetrahedron Letters.2011(38)
  • 4Fatemeh Khaleghi,Laily Bin Din,Ibrahim Jantan,Wan Ahmad Yaacob,Mohammad A. Khalilzadeh.A facile synthesis of novel 1,4-benzoxazepin-2-one derivatives[J].Tetrahedron Letters.2011(52)
  • 5Er-Yan Xia,Jing Sun,Rong Yao,Chao-Guo Yan.Synthesis of zwitterionic salts via three component reactions of nitrogen-containing heterocycles, acetylenedicarboxylate and cyclic 1,3-dicarbonyl compounds[J].Tetrahedron.2010(20)
  • 6Sakineh Asghari,Maryam Faraji-Najjarkolaee,Mohammad Ahmadipour.Regioselective vinylation of kojic acid using acetylenic esters in the presence of triphenylphosphine or tert -butyl isocyanide[J].Monatshefte für Chemie - Chemical Monthly.2010(7)
  • 7Issa Yavari,Zinatossadat Hossaini,Sanaz Souri,Samereh Seyfi.Diastereoselective synthesis of fused [1,3]thiazolo[1,3]oxazins and [1,3]oxazino[2,3-b][1,3]benzothiazoles[J].Molecular Diversity.2009(4)
  • 8Issa Yavari,Mohammad Piltan,Loghman Moradi.Synthesis of pyrrolo[2,1- a ]isoquinolines from activated acetylenes, benzoylnitromethanes, and isoquinoline[J].Tetrahedron.2009(10)
  • 9Mohammad Bagher Teimouri,Tayyebeh Abbasi,Saloomeh Ahmadian,Mohammad Reza Poor Heravi,Reihaneh Bazhrang.An efficient three-component protocol for the synthesis of novel spiro-oxazinobarbiturates[J].Tetrahedron.2009(39)
  • 10Ahmad Shaabani,Ali Hossein Rezayan,Afshin Sarvary,Marjan Heidary,Seik Weng Ng.Synthesis of highly stable unusual charge-separated pyridinium-, isoquinolinium-, quinolinium-, and N -methylimidazolium-tetronic acid zwitterions[J].Tetrahedron.2009(31)

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Chinese Chemical Letters
2014年 第3期

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