Green synthesis of novel bis(hexahydro-1H-xanthene-1,8(2H)-diones) employing p-toluenesulfonic acid (p-TSA) as a solid acid catalyst

被引:6
|
作者
Darweesh, Ahmed F. [1 ]
Salama, Soad K. [1 ]
Abdelhamid, Ismail A. [1 ]
Elwahy, Ahmed H. M. [1 ]
机构
[1] Cairo Univ, Fac Sci, Chem Dept, Giza 12613, Egypt
关键词
Bis(aldehydes); 55-dimethyl-13-cyclohexanedione; p-TSA bis(hexahydro-1H-xanthene-18(2H)-diones); ONE-POT SYNTHESIS; SOLVENT-FREE SYNTHESIS; LIGHT-EMITTING-DIODES; MULTICOMPONENT SYNTHESIS; XANTHENE DERIVATIVES; FUSED HETEROCYCLES; 3-COMPONENT SYNTHESIS; MOLECULAR-IODINE; EFFICIENT; ANTICANCER;
D O I
10.1080/00397911.2020.1837170
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Green synthesis of novel bis(hexahydro-1H-xanthene-1,8(2H)-diones) which are linked to aliphatic or aromatic spacers via ether or ester linkages were performed in good to excellent yields by the reaction of 5,5-dimethyl-1,3-cyclohexanedione with the appropriate bis-aldehydes using p-TSA as an organic acid solid catalyst. The reaction of the bis-aldehydes with barbituric acid or 1,3-dimethylbarbituric acid instead of 5,5-dimethyl-1,3-cyclohexanedione afforded the corresponding Knoevenagel condensation adducts in good yield.
引用
收藏
页码:471 / 484
页数:14
相关论文
共 50 条
  • [1] Synthesis, Crystal Structure, DFT Studies on Tetramethyl-(p-Tolyl)-Hexahydro-1H-Xanthene-1,8(2H)-Dione
    Fatima, Aysha
    Khanum, Ghazala
    Sharma, Arun
    Siddiqui, Nazia
    Butcher, R. J.
    Srivastava, Sanjay Kumar
    Javed, Saleem
    POLYCYCLIC AROMATIC COMPOUNDS, 2023, 43 (10) : 9210 - 9232
  • [2] SYNTHESIS AND BIOLOGICAL ACTIVITY OF TETRAMETHYL-HEXAHYDRO- 1H-XANTHENE-1,8(2H)-DIONEDERIVATIVES
    Choudhare, Sunil S.
    Khansole, Gopinath S.
    Karad, Ashok R.
    Wadwale, Navanand B.
    Bhosale, Vijay N.
    HETEROCYCLIC LETTERS, 2022, 12 (04): : 759 - 765
  • [3] Synthesis and antifungal screening of tetramethyl hexahydro-1H-xanthene-1,8(2H)-dione derivatives as potential inhibitors of morphogenesis and biofilm formation in Candida albicans
    Kasabe, Umesh I.
    Kale, Kishor B.
    Rode, Nitin R.
    Shelar, Amruta V.
    Patil, Rajendra H.
    Mhaske, Pravin C.
    Chaskar, Manohar G.
    NEW JOURNAL OF CHEMISTRY, 2022, 46 (05) : 2128 - 2139
  • [4] A Novel and Efficient Catalyst to One-Pot Synthesis of 2-Amino-4H-chromenes by p-Toluenesulfonic Acid
    Baghernejad, Bita
    Heravi, Majid M.
    Oskooie, Hossein A.
    JOURNAL OF THE KOREAN CHEMICAL SOCIETY-DAEHAN HWAHAK HOE JEE, 2009, 53 (06): : 631 - 634
  • [5] p-Toluenesulfonic acid-catalyzed regioselective C4-H iodination of isoquinolin-1(2H)-ones
    Yang, Cai-Yun
    Hu, Lin-Ping
    Zhang, De-Run
    Li, Xia
    Teng, Ming-Yu
    Liu, Bo
    Huang, Guo-Li
    NEW JOURNAL OF CHEMISTRY, 2022, 46 (22) : 10934 - 10939
  • [6] Efficient synthesis of bis-indolyloxindoles from (phenylimino)indolin-2-ones and 1H-indole catalyzed by p-toluenesulfonic acid
    Suresh, B.
    Brahmeshwary, G.
    Swamy, T.
    Gopi, I.
    Ravinder, V.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2016, 86 (05) : 1144 - 1150
  • [7] Efficient synthesis of bis-indolyloxindoles from (phenylimino)indolin-2-ones and 1H-indole catalyzed by p-toluenesulfonic acid
    B. Suresh
    G. Brahmeshwary
    T. Swamy
    I. Gopi
    V. Ravinder
    Russian Journal of General Chemistry, 2016, 86 : 1144 - 1150
  • [8] Kinetics of Reversible Oligomerization of L-Lactic Acid with a SnCl2•2H2O/p-Toluenesulfonic Acid Catalyst
    Baick, In Hak
    Luciani, Carla V.
    Park, Seung Young
    Lim, Taehoon
    Choi, Kyu Yong
    INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, 2012, 51 (51) : 16617 - 16625
  • [9] Multicomponent synthesis of 1-[aryl(p-tolylsulfanyl)methyl]naphthalen-2-ols using p-toluenesulfonic acid as a catalyst
    Hassanabadi, Alireza
    JOURNAL OF CHEMICAL RESEARCH, 2013, (03) : 152 - 154
  • [10] 9-(2,4-Dinitrophenyl)-3,3,6,6-tetramethyl- 3,4,5,6,7,9- hexahydro-1H-xanthene-1,8(2H)-dione
    Sureshbabu, N.
    Sughanya, V.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2013, 69 : O281 - +