One-pot synthesis of carbazole based 3-hydroxy-4H-chromen-4-ones by a modified Algar-Flynn-Oyamada reaction and their antimicrobial activity

被引:5
|
作者
Ashok, Dongamanti [1 ]
Ravi, Sidda [1 ]
Lakshmi, Bommidi Vijaya [1 ]
Ganesh, Arram [1 ]
机构
[1] Osmania Univ, Dept Chem, Hyderabad 500007, Andhra Pradesh, India
关键词
2-(9-ethyl-9H-carbazol-3-yl)-3-hydroxy-4H-chromen-4-ones; modified Algar-Flynn-Oyamada reaction; antimicrobial activity; MICROWAVE-ASSISTED SYNTHESIS; FLAVONOIDS; AGENTS;
D O I
10.2298/JSC141203051A
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new series of 2-(9-ethyl-9H-carbazol-3-yl)-3-hydroxy-4H-chromen-4-ones were synthesized from substituted 2-hydroxyacetophenones and 9-ethyl-9H-carbazole-3-carbaldehyde using NaOH and H2O2 by a modified Algar-Flynn-Oyamada reaction. In this method, the flavonols were synthesized in good yields (70-82 %) without isolating chalcones. The structures of the compounds were established based on H-1-NMR, C-13-NMR, FT-IR and mass spectral and analytical data. All the compounds were evaluated for their antimicrobial activity against bacteria, such as Staphylococus aureus, Bacillus subtilis, Escherichia coli and Klebsiella pneumoniae, as well as fungi, such as Aspergillus flavus and Fusarium oxysporum.
引用
收藏
页码:1361 / +
页数:9
相关论文
共 50 条
  • [41] One-pot synthesis of substituted quinazolin-4(3H)-ones under microwave irradiation
    Rad-Moghadam, K
    Khajavi, MS
    JOURNAL OF CHEMICAL RESEARCH-S, 1998, (11): : 702 - 703
  • [42] New one-pot synthesis of 4-hydroxyimino-5-polyfluoroalkylpyrazol-3-ones, their structure and biological activity
    Burgart, Yanina V.
    Agafonova, Natalya A.
    Shchegolkov, Evgeny V.
    Maslova, Vera V.
    Triandafilova, Galina A.
    Solodnikov, Sergey Yu.
    Krasnykh, Olga P.
    Saloutin, Victor I.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2019, 55 (01) : 52 - 59
  • [43] New one-pot synthesis of 4-hydroxyimino-5-polyfluoroalkylpyrazol-3-ones, their structure and biological activity
    Yanina V. Burgart
    Natalya A. Agafonova
    Evgeny V. Shchegolkov
    Vera V. Maslova
    Galina A. Triandafilova
    Sergey Yu. Solodnikov
    Olga P. Krasnykh
    Victor I. Saloutin
    Chemistry of Heterocyclic Compounds, 2019, 55 : 52 - 59
  • [44] SYNTHESIS, ANTIBACTERIAL, AND ANALGESIC ACTIVITY OF NOVEL 4-HYDROXY-3-(PHENYLTHIO)-2H-CHROMEN-2-ONES AND 4-HYDROXY-3-[IMIDAZOL/TETRAZOLO-2-yl)THIO]-2H-CHROMEN-2-ONES
    Rajesha, G.
    Mahadevan, Kittappa M.
    Satyanarayan, N. D.
    Naik, H. S. Bhojya
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2011, 186 (08) : 1733 - 1743
  • [45] A One-Pot Sonogashira Coupling and Annulation Reaction: An Efficient Route toward 4 H -Quinolizin-4-ones
    Chen, Zhengwang
    Liu, Tanggao
    Ma, Xiaoyue
    Liang, Pei
    Long, Lipeng
    Ye, Min
    SYNLETT, 2019, 30 (07) : 863 - 867
  • [46] One-Pot Synthesis of 3-Substituted 4H-Quinolizin-4-ones via Alkyne Substrate Control Strategy
    Fang, Ji-Wang
    Liao, Fang-jie
    Qian, Yang
    Dong, Chao-Chen
    Xu, Li-Jin
    Gong, Han-Yuan
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (04): : 3648 - 3655
  • [47] Synthesis of 3-Substituent-6-methoxy-7-hydroxy-4H-chromen-4-ones and the Related Unexpected Reactions
    Li, Hanbin
    Ren, Yi
    Zhang, Qian
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2011, 31 (04) : 563 - 566
  • [48] A NOVEL ONE-POT SYNTHESIS OF 2-ARYL-2H-1-BENZOPYRAN-3(4H)-ONES
    RAO, TS
    TRIVEDI, GK
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1985, 24 (11): : 1159 - 1160
  • [49] Synthesis and antimicrobial activity of some new 4-hydroxy-2H-1,4-benzoxazin-3(4H)-ones
    Özden, S
    Öztürk, AM
    Göker, H
    Altanlar, N
    FARMACO, 2000, 55 (11-12): : 715 - 718
  • [50] Synthesis and biological activities of new hydroxy-3-pyrazolyl-4H-chromen-4-ones and their o-glucosides
    Hatzade, K. M.
    Taile, V. S.
    Gaidhane, P. K.
    Haldar, A. G. M.
    Ingle, V. N.
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2008, 47 (08): : 1260 - 1270