An efficient three-component domino synthesis of difluoromethyl-containing 1,4-dihydropyridines under solvent and catalyst free conditions 被引量：1

An efficient three-component domino synthesis of difluoromethyl-containing 1,4-dihydropyridines under solvent and catalyst free conditions

原文传递

导出

摘要 The difluoromethyl-containing Hantzsch 1,4-dihydropyridines were synthesized in good yields by a one-pot cyclocondensation of ethyl difluoroacetoacetate (EDFAA),a variety of aromatic aldehydes and ammonium acetate under solvent and catalyst free conditions.The comparison of reaction conditions and products was made among the different 1,3-carbonyl substrates (ethyl acetoacetate,ethyl difluoroacetoacetate and ethyl trifluoroacetoacetate) for the Hantzsch reaction. The difluoromethyl-containing Hantzsch 1,4-dihydropyridines were synthesized in good yields by a one-pot cyclocondensation of ethyl difluoroacetoacetate (EDFAA),a variety of aromatic aldehydes and ammonium acetate under solvent and catalyst free conditions.The comparison of reaction conditions and products was made among the different 1,3-carbonyl substrates (ethyl acetoacetate,ethyl difluoroacetoacetate and ethyl trifluoroacetoacetate) for the Hantzsch reaction.

作者 LI Hui YU JinLong CAO Song SHEN Li WU MingXi CHENG JianHang QIAN XuHong

机构地区 Shanghai Key Laboratory of Chemical Biology

出处《Science China Chemistry》 SCIE EI CAS 2010年第7期1509-1513,共5页 中国科学(化学英文版)

基金 supported by the National Basic Research Program of China (2010CB126101) Shanghai Foundation of Science and Technology (09391911800) the National High Technology Research and Development Program of China (2006AA10A201) the Shanghai Leading Academic Discipline Project (B507)

关键词 THREE-COMPONENT difluoromethyl 1 4-dihydropyridines ethyl difluoroacetoacetate three-component difluoromethyl 1,4-dihydropyridines ethyl difluoroacetoacetate

分类号 O621.3 [理学—有机化学]

引文网络
相关文献

参考文献19

1Phlip LG,Keith LJ. WO patent,2009002809 . 2008
2Brookes PS,Richard F. US patent,2009149540 . 2009
3Hu JB,Zhang W,Wang F.Selective difluoromethylation and mon- ofluoromethylation reactions. Chemical Communications . 2009
4Hu JB.Nucleophilic,radical,and electrophilic (phenylsulfonyl) di- fluoromethylations. Journal of Fluorine Chemistry . 2009
5Saini A,Kumar S,Sandhu JS.Hantzsch reaction: Recent advances in Hantzsch 1,4-dihydropyridines. J Indust Res . 2008
6Reddy GM,Shiradkar M,Chakravarthy AK.Chemical and pharmacological significance of 1,4-dihydropyridines. Current Organic Chemistry . 2007
7Liu NJ,Cao S,Wu JJ,Yu JL,Shen L,Feng X,Qian XH.Solvent- free Ugi four-component condensation: Application to synthesis of philanthotoxins-12 analogues. Tetrahedron . 2008
8Shen L,Zhang J,Cao S,Yu JL,Liu NJ,Wu JJ,Qian XH.One-pot synthesis of trifluoromethyl-containing pyrazoles via sequential Yb(PFO)3-catalyzed three-component reaction and IBX-mediated oxidation. Synlett . 2008
9Fang LL. EP patent,0133612 . 1985
10Katsuyama I,Funabiki K,Matsui M,Muramatsu H,Shibata K.An efficient synthesis of 1,4-dihydro-6-trifluoromethylpyridines: a facile and useful method for dehydration of -trifluoromethyl alcohols by use of phosphorous oxychloride/pyridine adsorbed on silica gel. Heterocycles . 2006

同被引文献86

1Professor LIU Yu Department of Chemistry Nankai University,Tianjin.Preface to the special issue:Macrocyclic and supramolecular chemistry[J].Science China Chemistry,2009,52(4):401-401. 被引量：4
2XIE LinHua1, LIN JianBin1, LIU XiaoMin1, XUE Wei1, ZHANG WeiXiong1, LIU ShuXia2, ZHANG JiePeng1 & CHEN XiaoMing1 1MOE Key Laboratory of Bioinorganic and Synthetic Chemistry,State Key Laboratory of Optoelectronic Materials and Technologies,School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou 510275, China 2Key Laboratory of Polyoxometalates Science of Ministry of Education,College of Chemistry, Northeast Normal University, Changchun 130024, China.Organic ammonium ion-occluded flexible coordination polymers:Thermal activation,structure transformation and proton transfer[J].Science China Chemistry,2010,53(10):2144-2151. 被引量：4
3XIA Qing, FENG XuDong, YUAN Lan, WANG Kui & YANG XiaoDa State Key Laboratory of Natural and Biomimetic Drugs and Department of Chemical Biology,School of Pharmaceutical Sciences, Peking University, Beijing 100191, China.Brain-derived neurotrophic factor protects neurons from GdCl_3-induced impairment in neuron-astrocyte co-cultures[J].Science China Chemistry,2010,53(10):2193-2199. 被引量：3
4GENG YanHou1,HUANG Li1,2,WU ShuPeng1,2 & WANG FoSong1 1State Key Laboratory of Polymer Physics and Chemistry,Changchun Institute of Applied Chemistry,Chinese Academy of Sciences,Changchun 130022,China 2Graduate University of Chinese Academy of Sciences,Beijing 100049,China.Kumada chain-growth polycondensation as a universal method for synthesis of well-defined conjugated polymers[J].Science China Chemistry,2010,53(8):1620-1633. 被引量：2
5GAO HaiYang1,2,HU Hao1 & WU Qing1,2 1Institute of Polymer Science,School of Chemistry and Chemical Engineering,Sun Yat-Sen (Zhongshan) University,Guangzhou 510275,China 2Key Laboratory for Polymeric Composite and Functional Materials of Ministry of Education,Sun Yat-Sen (Zhongshan) University,Guangzhou 510275,China.High norbornene incorporation in ethylene-norbornene copolymerization with a bis(α-alkyloxoimine) titanium-MAO catalyst[J].Science China Chemistry,2010,53(8):1634-1640. 被引量：2
6PANG XinChang,JING RongKuan,PAN MuGang & HUANG JunLian Key Laboratory of Molecular Engineering of Polymers,Ministry of Education,Department of Macromolecular Science,Fudan University,Shanghai 200433,China.A pH-and temperature-sensitive macrocyclic graft copolymer composed of PEO ring and multi-poly(2-(dimethylamino) ethyl methacrylate) lateral chains[J].Science China Chemistry,2010,53(8):1653-1662. 被引量：6
7MA HuiLi & LIANG Xing-Jie Chinese Academy of Sciences Key Laboratory for Biomedical Effects of Nanomaterials and Nanosafety,National Center for Nanoscience and Technology,Beijing 100190,China.Fullerenes as unique nanopharmaceuticals for disease treatment[J].Science China Chemistry,2010,53(11):2233-2240. 被引量：3
8LE GUYADER Laurent.“Smart”nanomaterials for cancer therapy[J].Science China Chemistry,2010,53(11):2241-2249. 被引量：4
9WANG Jian 1,MEI Ju 1,QIN AnJun 1,SUN JingZhi 1 & TANG Ben Zhong 1,2 1 MOE Key Laboratory of Macromolecular Synthesis and Functionalization,Department of Polymer Science and Engineering,Institute of Biomedical Macromolecules,Zhejiang University,Hangzhou 310027,China 2 Department of Chemistry,The Hong Kong University of Science & Technology,Hong Kong,China.Stimulus responsive fluorescent hyperbranched polymers and their applications[J].Science China Chemistry,2010,53(12):2409-2428. 被引量：3
10ZHOU ZhiPing 1 & YAN DeYue 2 1 School of Materials Science and Engineering,Jiangsu University,Zhenjiang 212013,China 2 School of Chemistry and Chemical Engineering,Shanghai Jiao Tong University,Shanghai 200240,China.Kinetic theory of self-condensing vinyl polymerization[J].Science China Chemistry,2010,53(12):2429-2439. 被引量：5

引证文献1

1SONG GuanQun,ZHU XiaoWen.Development of Science China Chemistry during 2008-2012:From the perspective of Special Issues/Topics[J].Science China Chemistry,2012,55(12):2617-2626. 被引量：2

二级引证文献2

1朱晓文,宋冠群.编委会对提高期刊质量所起的作用[J].编辑学报,2013,25(6):564-566. 被引量：66
2朱晓文,宋冠群.期刊的学术质量建设——以《中国科学:化学》为例[J].中国科技期刊研究,2014,25(1):121-123. 被引量：7

1Man LU,Jian Guo FANG,Zhong Li LIU,Long Min WU.Novel Reaction of Nitroxide with Hantzsch Dihydropyridines[J].Chinese Chemical Letters,2002,13(10):923-925.
2Li, Jianping Qiu, Jikuan Li, Huijuan Zhang, Guisheng.An Efficient, Three-component One-pot Preparation of 1,4-Dihydropyridines Containing Novel Substituted Pyrazole under Sulfamic Acid Catalysis[J].Chinese Journal of Chemistry,2011,29(3):511-514. 被引量：1
3Hakimeh MIRZAEI,Abolghasem DAVOODNIA.微波辅助溶胶-凝胶法合成MgO纳米粒子及其催化合成Hantzsch1,4-二氢吡啶性能(英文)[J].催化学报,2012,33(9):1502-1507. 被引量：6
4Wang CHEN,Mei Zhong JIN,Zhong li LIU,Long Min WU(National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000).Novel Reaction of Nitrosonium(NO^+) with Hantzsch Dihydropyridines[J].Chinese Chemical Letters,1999,10(12):991-994. 被引量：1
5Kamalakar P.Nandre,Jagdish K.Salunke,Jitendra P.Nandre,Vijay S.Patil,Amul U.Borse,Sidhanath V.Bhosale.Glycerol mediated synthesis of 5-substituted lH-tetrazole under catalyst free conditions[J].Chinese Chemical Letters,2012,23(2):161-164. 被引量：2
6Leila Zare,Mohammad Nikpassand.Multicomponent synthesis of dihydropyridines catalyzed by L-proline[J].Chinese Chemical Letters,2011,22(5):531-534. 被引量：2
7JIA Xu-dong DUAN Hal-feng LIN Ylng-jle CAO Jun-gang LIANG Da-peng WU Mao-cheng.One-pot Three-component Synthesis of 4,4'-Arylidene-bis(3-methyl-pyrazolones) Derivatives in Water[J].Chemical Research in Chinese Universities,2012,28(6):999-1002.
8WU Ping,XIA Er-yan,SUN Jing,YAN Chao-guo.Synthesis of Polysubstituted 1,4-Dihydropyridines via Four-component Reactions of Arylamine,Acetylenedicarboxylate, Aromatic Aldehyde and Ethyl Acetoacetate[J].Chemical Research in Chinese Universities,2012,28(4):652-655.
9M.Kooti,P.Kharazi,H.Motamedi.Preparation and Antibacterial Activity of Three-component NiFe_2O_4@PANI@Ag Nanocomposite[J].Journal of Materials Science & Technology,2014,30(7):656-660. 被引量：1
10Zeinab Pourghobadi,Fatemeh Derikvand.H_3PMo_(12)O_(40) catalyzed three-component one-pot synthesis of 4,6-diarylpyrimidin-2(1H)-ones under solvent-free conditions[J].Chinese Chemical Letters,2010,21(3):269-272.

Science China Chemistry

2010年第7期

浏览历史

内容加载中请稍等...

An efficient three-component domino synthesis of difluoromethyl-containing 1,4-dihydropyridines under solvent and catalyst free conditions 被引量：1

参考文献19

同被引文献86

引证文献1

二级引证文献2

相关作者

相关机构

相关主题

浏览历史