One-pot Three-component Route for the Synthesis of Functionalized 4H-chromenes Catalyzed by ZrOCl2•8H2O in Water

被引:13
|
作者
Halimehjani, Azim Ziyaei [1 ]
Keshavarzi, Nahid [2 ]
机构
[1] Kharazmi Univ, Fac Chem, 49 Mofateh St, Tehran, Iran
[2] Sharif Univ Technol, Dept Chem, POB 11465-9516, Tehran, Iran
关键词
BETA-AMINO KETONES; IN-VITRO; MULTICOMPONENT REACTIONS; SELECTIVE SYNTHESIS; DOMINO REACTIONS; NAPHTHOPYRAN DERIVATIVES; CONJUGATE ADDITION; EFFICIENT; CHROMENES; ACID;
D O I
10.1002/jhet.3081
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient method for the synthesis of functionalized 4H-chromenes via a one-pot three-component condensation reaction of a 2-hydroxybenzaldehyde with an active methylene compound and a carbon-based nucleophile in the presence of a catalytic amount of ZrOCl(2)8H(2)O in water under thermal condition has been described. High yields, simple work-up procedure, performing reactions in water and synthesis of complex molecules with a one-pot procedure are the main advantages of this procedure. In addition, the structure of the product from the condensation of salicylaldehyde, 2-naphthol, and dimedone was confirmed by X-ray crystallography.
引用
收藏
页码:522 / 529
页数:8
相关论文
共 50 条
  • [21] Triton B Catalyzed Three-Component, One-Pot Synthesis of 2-Amino-2-chromenes at Ambient Temperature
    Sabitha, Gowravaram
    Bhikshapathi, M.
    Nayak, Sambit
    Srinivas, R.
    Yadav, J. S.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2011, 48 (02) : 267 - 271
  • [22] Highly anti-anti selective synthesis of bis-β-amino ketones via three-component direct Mannich-type reaction of terephthalaldehyde catalyzed by ZrOCl2•8H2O
    Eftekhari-Sis, Bagher
    Saraei, Mahnaz
    Bonyad-Bagheri, Mohammad
    JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2013, 10 (03) : 421 - 427
  • [23] Zirconium(IV) Oxychloride Octahydrate (ZrOCl2·8H2O): An Efficient Catalyst for the One-Pot Multicomponent Synthesis of Hexahydroquinoline Derivatives under Conventional Heating and Microwave Irradiation
    S. Tasqeeruddin
    Y. I. Asiri
    S. Shaheen
    Russian Journal of Organic Chemistry, 2022, 58 : 1008 - 1014
  • [24] Zirconium(IV) Oxychloride Octahydrate (ZrOCl2•8H2O): An Efficient Catalyst for the One-Pot Multicomponent Synthesis of Hexahydroquinoline Derivatives under Conventional Heating and Microwave Irradiation
    Tasqeeruddin, S.
    Asiri, Y., I
    Shaheen, S.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 58 (07) : 1008 - 1014
  • [25] Enantioselective One-Pot Synthesis of 2-Amino-4-(indol-3-yl)-4H-Chromenes
    Chen, Weiliang
    Cai, Yunfei
    Fu, Xuan
    Liu, Xiaohua
    Lin, Lili
    Feng, Xiaoming
    ORGANIC LETTERS, 2011, 13 (18) : 4910 - 4913
  • [26] Facile construction of densely functionalized 4H-chromenes via three-component reactions catalyzed by L-proline
    Li, Minghao
    Zhang, Biao
    Gu, Yanlong
    GREEN CHEMISTRY, 2012, 14 (09) : 2421 - 2428
  • [27] One-Pot Three-Component Route for the Synthesis of Rhodanine Derivatives in Water
    Halimehjani, Azim Ziyaei
    Hosseinkhany, Samaneh
    SYNTHESIS-STUTTGART, 2015, 47 (20): : 3147 - 3152
  • [28] Efficient Three-Component One-Pot Synthesis of 4H-Pyrans
    J. Malviya
    S. Kala
    L. K. Sharma
    R. K. P. Singh
    Russian Journal of Organic Chemistry, 2019, 55 : 686 - 693
  • [29] Efficient Three-Component One-Pot Synthesis of 4H-Pyrans
    Malviya, J.
    Kala, S.
    Sharma, L. K.
    Singh, R. K. P.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 55 (05) : 686 - 693
  • [30] An Efficient and Chemoselective Knoevenagel/Hemiketalization Process for the Synthesis of New 2H-Chromenes in a One-Pot Three-Component Reaction
    Rao, Lenka Chandrasekhara
    Kumar, Nandigama Satish
    Meshram, Harshadas Mitaram
    HELVETICA CHIMICA ACTA, 2015, 98 (07) : 978 - 985