[1]余 飞,黄荣璐,徐 绘,等.邻氨基二苯乙烯与1,3-环己二酮的串联环化反应合成1,4-二氢喹啉衍生物[J].常州大学学报(自然科学版),2019,31(03):34-39.[doi:10.3969/j.issn.2095-0411.2019.03.003]
　YU Fei,HUANG Ronglu,XU Hui,et al.Synthesis of 1,4-Dihydroquinoline Derivatives via Cascade Cyclization of o-Aminodistyrene with 1,3-Cyclohexanedione[J].Journal of Changzhou University(Natural Science Edition),2019,31(03):34-39.[doi:10.3969/j.issn.2095-0411.2019.03.003]
点击复制

邻氨基二苯乙烯与1,3-环己二酮的串联环化反应合成1,4-二氢喹啉衍生物()
分享到：

常州大学学报(自然科学版)[ISSN:2095-0411/CN:32-1822/N]

卷:
第31卷
期数:
2019年03期
页码:
34-39
栏目:
化学化工
出版日期:
2019-05-28

文章信息/Info

Title:
Synthesis of 1,4-Dihydroquinoline Derivatives via Cascade Cyclization of o-Aminodistyrene with 1,3-Cyclohexanedione
文章编号:
2095-0411(2019)03-0034-06
作者:
余 飞; 黄荣璐; 徐 绘; 张 泽
(安徽工程大学 生物与化学工程学院,安徽 芜湖 241000)
Author(s):
YU Fei;  HUANG Ronglu;  XU Hui;  ZHANG Ze
(School of Biological and Chemical Engineering, Anhui Polytechnic University, Wuhu 241000, China)
关键词:
1; 4-二氢喹啉;  碘;  迈克尔加成;  串联反应
Keywords:
1; 4-dihydroquinoline;  iodine;  Michael addition;  cascade reaction
分类号:
O 621.3
DOI:
10.3969/j.issn.2095-0411.2019.03.003
摘要:
先以廉价易得的取代苯胺和苯乙炔为底物合成邻氨基二苯乙烯,再与1,3-环己二酮在甲苯中碘催化作用下加热反应,通过缩合-加成串联环化反应高效合成了8个新型的1,4-二氢喹啉类衍生物,分离产率高达85%～94%,并通过熔点、核磁1H NMR及13C NMR分析手段对所有产物进行了结构表征。该方法原料及催化剂便宜易得,操作简便,合成效率高。
Abstract:
Firstly, o-aminodistyrenes were synthesized from cheap and easily available substituted anilines and phenylacetylenes. The condensation-addition cascade cyclization of these o-aminodistyrenes with 1,3-cyclohexadiones can be efficiently accomplished by heating in toluene in presence of iodine. Following this method, eight novel 1,4-dihydroquinolines were obtained in 85%—94% isolated yields. All the products were characterized by melting point, 1H NMR and 13C NMR analysis. This method exhibits advantages of using cheap and easily available starting materials and catalyst, easy operation and high efficiency.

参考文献/References:

[1]YONA L, SUNG K. Synthesis antibacterial and antifungal evaluation of novel 1,4-dihydropyridine derivatives[J]. Journal of Organic Chemistry, 2016, 17(7): 8234-8239.
[2]GUPTA V, MISRA U. Synthesis and cardiorascular activity of difluro-substituted hexahydroquinoline[J]. Medicinal Chemistry Research, 2017, 17(11): 437-444.
[3]PARTHA V, CRAIGE T, SIARMA R, et al. Design and synthesis of 1,4-disubstituted polyhydroquinolines as prospective antihyperglycemic[J]. Bioorganic & Medicinal Chemistry, 2017, 22(2): 856-869.
[4]YANG X L, QIAN X, CAO R, et al. The crystal structure of 7-bromo-1-cyclopropyl-8- methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid an intermediate of the ozenoxacin synthesis[J]. Organic & Biomolecular Chemistry, 2018, 233(4): 667-671.
[5]PYRIH A, BERNINGER M, GZELLA A, et al. Synthesis and evaluation of antitrypanosomal activity of some thiosemicarbazide derivatives of 1-butyl-6-fluoro-7-morpholino-4-oxo-1,4-dihydroquinoline-3-carboxylic acid[J]. Synthetic Communications, 2018, 48(14): 1883-1891.
[6]DONG Y X, DONG L, CHEN J L, et al. Synthesis and biological evaluation of N-alkyl-1,4-dihydroquinoline prodrugs of scutellarin methyl ester as neuroprotective agents[J]. Medicinal Chemistry Research, 2018, 27(4): 1111-1121.
[7]TAN L, ZHANG Z, GAO DL, et al. 4-oxo-1,4-dihydroquinoline-3-carboxamide derivatives as new Axlkinase inhibitors[J]. Journal of Medicinal Chemistry, 2016, 28(14): 6807-6825.
[8]OKAMURA T, OKADA M, KIKUCHI T, et al. A 11C-labeled 1,4-dihydroquinoline derivative as a potential PET tracer for imaging of redox status in mouse brain[J]. Journal of Cerebral Blood Flow & Metabolism, 2015, 18(12): 1930-1936.
[9]ZHANG X S, SONG X X, LI H, et al. An organocatalytic cascade approach toward polysubstituted quinolines and chiral 1,4-dihydroquinolines-unanticipated effect of N-protecting groups[J]. Angewandte Chemie International Edition, 2012, 51(29): 7282-7286.
[10]LAURENTIZ R S, GOMES W P, PISSURNO A R, et al. Synthesis and antibacterial activity of new lactone 1,4-dihydroquinoline derivatives[J]. Medicinal Chemistry Research, 2018, 27(4): 1074-1084.
[11]FELTS A S, RODRIGUEZ A L, SMITH K A, et al. Design of 4-oxo-1-aryl-1,4-dihydroquinoline-3-carboxamides as selective negative allosteric modulators of metabotropic glutamate receptor subtype 2[J]. Journal of Medicinal Chemistry, 2015, 58(22): 9027-9040.
[12]ARIENTI A, BIGI F, MAGGI R, et al. Regioselective electrophilic alkylation of anilines with phenylacetylene in the presence of montmorillonite KSF[J]. Tetrahedron, 1997, 25(10): 3795-3804.

相似文献/References:

[1]陶永新,等.侧链含2, 5- 二苯基- 1, 3, 4- 噻二唑聚乙烯的 制备及其性能[J].常州大学学报(自然科学版),2009,(04):16.
　TAO Yong- x in,YANG Xue- bo,et al.Study of Synthesis and Properties of Polystyrene Containing 2, 5- Diphenyl- 1, 3, 4- Thiadiazole in Side Chain[J].Journal of Changzhou University(Natural Science Edition),2009,(03):16.
[2]邱滔,阚明玺,吕新宇.1,4-二羟基蒽醌废水中邻苯二甲酸的吸附回收[J].常州大学学报(自然科学版),2011,(04):28.
　QIU Tao,KAN Ming-xi,LV Xin-yu.Study of the Recovery of o-Phthalic Acid in 1,4- Dihydroxy Anthraquinone Industrial Wastewater[J].Journal of Changzhou University(Natural Science Edition),2011,(03):28.
[3]杨珊珊,刘总堂,邢 蓉,等.羧基修饰的吸附树脂对1,2-苯并异噻唑-3-酮(BIT)的吸附研究[J].常州大学学报(自然科学版),2013,(03):1.[doi:10.3969/j.issn.2095-0411.2013.03.001]
　YANG Shan shan,LIU Zong tang,XING Rong,et al.Study on the Adsorption of 1,2-Benzisothiazolin-3-One(BIT) with the Adsorption Resins Modified with Carboxyl[J].Journal of Changzhou University(Natural Science Edition),2013,(03):1.[doi:10.3969/j.issn.2095-0411.2013.03.001]
[4]种国双,路建美,陶永新.末端含1,3,4 -噻二唑聚苯乙烯的AT RP 合成及其荧光性能研究[J].常州大学学报(自然科学版),2007,(04):1.
　CHONG Guo -shuang,LU Jian -mei,TAO Yong -xin.Study of Synthesis and Fluorescent Properties of Polystyrene Containing 1,3,4 -thiadiazole End Group by Atom Transfer Radical Polymerization[J].Journal of Changzhou University(Natural Science Edition),2007,(03):1.
[5]梁翠荣,金桂花,吴胜楠,等.点击化学应用于合成1,2,3-三唑衍生物的研究进展[J].常州大学学报(自然科学版),2015,(01):54.[doi:10.3969/ j.issn.2095-0411.2015.01.011]
　LIANG Cui-rong,JIN Gui-hua,WU Sheng-nan,et al.Recent Progress in Application of Click Chemistry in the Synthesis of 1,2,3-Triazoles Derivatives[J].Journal of Changzhou University(Natural Science Edition),2015,(03):54.[doi:10.3969/ j.issn.2095-0411.2015.01.011]
[6]杨?? 扬,席海涛,殷开梁,等.1, 3- 二( 4- 硝基苯氧基) - 2- 丙醇结构的研究[J].常州大学学报(自然科学版),2003,(02):26.
　YANG Yang,XI Hai- tao,YIN Kai- liang,et al.The Study of Structure of 1, 3- Bis ( 4- Nitrophenoxy ) - 2- Propylalcohol Using NMR and Molecular Modeling[J].Journal of Changzhou University(Natural Science Edition),2003,(03):26.
[7]李正义,钱纪生,殷乐,等.1，3氧杂螺环化合物的合成[J].常州大学学报(自然科学版),2016,(02):24.[doi:10.3969/j.issn.2095-0411.2016.02.005]
　LI Zhengyi,QIAN Jisheng,YIN Yue,et al.Synthesis of 1,3OxoSpirocyclic Compounds[J].Journal of Changzhou University(Natural Science Edition),2016,(03):24.[doi:10.3969/j.issn.2095-0411.2016.02.005]

备注/Memo

备注/Memo:
收稿日期:2018-10-20。
基金项目:国家自然科学基金资助项目(21242013); 国家级大学生创新训练计划(201810363053)。
作者简介:余飞(1993—),男,安徽安庆人,硕士生。通信联系人:张泽(1976—),E-mail: zzhang@ahpu.edu.cn
更新日期/Last Update: 2019-05-29