One-pot, three-component, selective synthesis of the polyfunctionalized 4H-pyran and 4H-benzo[b]pyran derivatives in the presence of a highly efficient molecular sieve-supported zinc catalyst

被引:18
|
作者
Magyar, Agnes [1 ]
Hell, Zoltan [1 ]
机构
[1] Budapest Univ Technol & Econ, Dept Organ Chem & Technol, Muegyet Rkp 3, H-1111 Budapest, Hungary
关键词
heterogeneous catalysis; molecular sieve; multicomponent reactions; polyfunctionalized 4H-pyrans and 4H-benzo[b]pyrans; zinc; MIXED-OXIDE CATALYST; AQUEOUS-MEDIA; GREEN SYNTHESIS; IONIC LIQUID; MULTICOMPONENT SYNTHESIS; HETEROGENEOUS CATALYST; RECYCLABLE CATALYST; PYRANS; NITRILES; PYRIMIDINES;
D O I
10.1515/gps-2017-0083
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A series of pentasubstituted 4H-pyrans and tetrahydrobenzo[b]pyrans are synthesized with excellent yields via a one-pot condensation of aromatic aldehydes, malononitrile, and a dicarbonyl compound, ethyl acetoacetate, acetyl-acetone or dimedone, in the presence of 4 angstrom molecular sieve modified with zinc(II) as heterogeneous catalyst, in ethanol. The process offers numerous advantages, such as better yield, short reaction time, and mild reaction conditions. The catalyst's preparation is simple and it could be reused while still maintaining its activity.
引用
收藏
页码:316 / 322
页数:7
相关论文
共 50 条
  • [1] An efficient synthesis of 4H-chromene, 4H-pyran, and oxepine derivatives via one-pot three-component tandem reactions
    Kazemi, Bagher
    Javanshir, Shahrzad
    Maleki, Ali
    Safari, Mostafa
    Khavasi, Hamid Reza
    [J]. TETRAHEDRON LETTERS, 2012, 53 (51) : 6977 - 6981
  • [2] One-pot synthesis of polyfunctionalized 4H-pyran derivatives bearing fluorochloro pyridyl moiety
    Ye, Zhenjun
    Xu, Renbo
    Shao, Xusheng
    Xu, Xiaoyong
    Li, Zhong
    [J]. TETRAHEDRON LETTERS, 2010, 51 (38) : 4991 - 4994
  • [3] ONE-POT, CATALYST-FREE SYNTHESIS OF SPIROOXINDOLE AND 4H-PYRAN DERIVATIVES
    Ponpandian, Thanasekaran
    Muthusubramanian, Shanmugam
    [J]. SYNTHETIC COMMUNICATIONS, 2014, 44 (06) : 868 - 874
  • [4] [DMImd-DMP]: A highly efficient and reusable catalyst for the synthesis of 4H-benzo[b]pyran derivatives
    Redouane, Mohamed Abdenour
    Khiri-Meribout, Naima
    Benzerka, Saida
    Debache, Abdelmadjid
    [J]. HETEROCYCLIC COMMUNICATIONS, 2019, 25 (01) : 167 - 179
  • [5] One-Pot Synthesis of Functionalized Fused 4H-Pyran Systems
    Bayat, Mohammad
    Shiraz, Nader Zabarjad
    Asayesh, Soheila Shafei
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2010, 47 (04) : 857 - 860
  • [6] Three component one-pot synthesis of 4H-benzo-[b]-pyran derivatives using [(diacetoxyiodo)benzene] (DIB) as a hypervalent iodine catalyst
    Waghmare, Amit S.
    Pandit, Shivaji S.
    [J]. IRANIAN CHEMICAL COMMUNICATION, 2015, 3 (04) : 291 - 301
  • [7] Efficient Synthesis of 4-Phenyl-4H-pyran Derivatives via a DIPEA-catalyzed One-Pot Three-Component Reaction
    Jun Li
    Jie Li
    Shi-yu Hu
    Ye Chen
    Ju Liu
    [J]. Russian Journal of Organic Chemistry, 2019, 55 : 1791 - 1799
  • [8] Efficient Synthesis of 4-Phenyl-4H-pyran Derivatives via a DIPEA-catalyzed One-Pot Three-Component Reaction
    Li, Jun
    Li, Jie
    Hu, Shi-yu
    Chen, Ye
    Liu, Ju
    [J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 55 (11) : 1791 - 1799
  • [9] Natural Deep Eutectic Solvent as a Green Catalyst for the One-pot Synthesis of Chromene and 4H-Pyran Derivatives
    Valipour, Zohreh
    Hosseinzadeh, Rahman
    Sarrafi, Yaghoub
    Maleki, Behrooz
    [J]. ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2024, 56 (02) : 105 - 117
  • [10] Polypyrrole/Fe3O4/CNT as a recyclable and highly efficient catalyst for one-pot three-component synthesis of pyran derivatives
    Hojati, Seyedeh Fatemeh
    Amiri, Amirhassan
    MoeiniEghbali, Nasrin
    Mohamadi, Sakineh
    [J]. APPLIED ORGANOMETALLIC CHEMISTRY, 2018, 32 (04)