ULTRASOUND-ASSISTED, ONE-POT, FOUR-COMPONENT SYNTHESIS OF 1,4,6,8-TETRAHYDROQUINOLINES IN AQUEOUS MEDIUM

被引:14
|
作者
Siddekha, Aisha [1 ,2 ]
Azzam, Sadeq Hamood Saleh [1 ]
Pasha, M. A. [1 ]
机构
[1] Bangalore Univ, Dept Studies Chem, Bangalore 560001, Karnataka, India
[2] Smt VHD Cent Inst Home Sci, Dept Chem, Bangalore, Karnataka, India
关键词
2-Amino-3-cyano-4-aryl-5-oxo-7; 7-dimethyl-1; 4; 6; 8-tetrahydroquinolines; aromatic aldehydes; malononitrile; potassium carbonate; ultrasonication; water; MULTICOMPONENT REACTIONS; POLYHYDROQUINOLINE DERIVATIVES; SOLVENT-FREE; EFFICIENT; QUINOLONE; WATER; COPOLYMERS; INHIBITORS; CHEMISTRY; POLYMERS;
D O I
10.1080/00397911.2013.813545
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of 2-amino-3-cyano-4-aryl-5-oxo-7,7-dimethyl-1,4,6,8-tetrahydroquinolines were prepared by a one-pot, four-component condensation of aromatic aldehydes, dimedone, malononitrile, and ammonium acetate using K2CO3 as a catalyst in aqueous medium under sonic conditions. This protocol, being a single-step reaction, has the advantages of operational simplicity and minimal environmental impact. The synthesized compounds were confirmed through spectral characterization using infrared, H-1 NMR, C-13 NMR, and CHN analysis. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]
引用
收藏
页码:424 / 432
页数:9
相关论文
共 50 条
  • [1] CTACl AS CATALYST FOR FOUR-COMPONENT, ONE-POT SYNTHESIS OF PYRANOPYRAZOLE DERIVATIVES IN AQUEOUS MEDIUM
    Wu, Mingshu
    Feng, Qinqin
    Wan, Dehui
    Ma, Jinya
    SYNTHETIC COMMUNICATIONS, 2013, 43 (12) : 1721 - 1726
  • [2] Ultrasound-assisted one-pot, four component synthesis of 4-aryl 3,4-dihydropyridone derivatives
    Ruiz, Enrique
    Rodriguez, Hortensia
    Coro, Julieta
    Salfran, Esperanza
    Suarez, Margarita
    Martinez-Alvarez, Roberto
    Martin, Nazario
    ULTRASONICS SONOCHEMISTRY, 2011, 18 (01) : 32 - 36
  • [3] An Ultrasound-Assisted Solvent and Catalyst-Free Synthesis of Structurally Diverse Pyrazole Centered 1,5-disubstituted Tetrazoles via One-Pot Four-Component Reaction
    Swami, Suman
    Shrivastava, Rahul
    Sharma, Neelam
    Agarwala, Arunava
    Verma, Ved Prakash
    Singh, Atul Pratap
    LETTERS IN ORGANIC CHEMISTRY, 2022, 19 (09) : 795 - 802
  • [4] One-Pot, Sequential Four-Component Synthesis of Thiazepine Derivatives
    Alizadeh, Abdolali
    Feizabadi, Masoomeh
    Bayat, Fahimeh
    Zhu, Long-Guan
    SYNLETT, 2014, 25 (09) : 1267 - 1270
  • [5] Four-component one-pot synthesis of novel dicyanoaniline-anchored triazoles
    Mojtahedi, Mohammad M.
    Azhari, Saeede
    Abaee, M. Saeed
    CANADIAN JOURNAL OF CHEMISTRY, 2022, : 561 - 567
  • [6] A straightforward and sustainable one-pot, four-component synthesis of rhodanine derivatives
    Azizi, Najmedin
    Hasani, Morteza
    Khajeh, Meysam
    Edrisi, Mahtab
    TETRAHEDRON LETTERS, 2015, 56 (10) : 1189 - 1192
  • [7] Meglumine promoted one-pot, four-component synthesis of pyranopyrazole derivatives
    Guo, Rui-Yun
    An, Zhi-Min
    Mo, Li-Ping
    Yang, Shu-Tao
    Liu, Hong-Xia
    Wang, Shu-Xia
    Zhang, Zhan-Hui
    TETRAHEDRON, 2013, 69 (47) : 9931 - 9938
  • [8] Pyrrolidine-Catalyzed Four-Component One-Pot Synthesis of Dihydropyrano[2,3-C]Pyrazole Derivatives
    Wang Liju
    Ablajan, Keyume
    CURRENT ORGANIC SYNTHESIS, 2014, 11 (02) : 310 - 316
  • [9] One-pot four-component synthesis of some novel octahydroquinolindiones using ZnO as an efficient catalyst in water
    Azzam, Sadeq Hamood Saleh
    Siddekha, Aisha
    Pasha, M. A.
    TETRAHEDRON LETTERS, 2012, 53 (46) : 6306 - 6309
  • [10] Synthesis of pyrimido[6,1-a]isoquinolines via a one-pot, four-component reaction
    Alizadeh, Abdolali
    Rezvanian, Atieh
    Zhu, Log-Guan
    TETRAHEDRON, 2010, 66 (34) : 6924 - 6927