Application of nitrogen-rich porous organic polymer for the solid-phase synthesis of 2-amino-4H-benzo[b]pyran scaffolds using ball milling process

被引:15
作者
Zaharani, Lia [1 ]
Khaligh, Nader Ghaffari [1 ]
Mihankhah, Taraneh [2 ]
Johan, Mohd Rafie [1 ]
机构
[1] Univ Malaya, Inst Postgrad Studies, Nanotechnol & Catalysis Res Ctr, Kuala Lumpur 50603, Malaysia
[2] Iran Univ Sci & Technol, Sch Civil Engn, Dept Water & Environm Engn, Environm Res Lab, Tehran 16765163, Iran
关键词
Porous polymer; Heterogeneous catalysis; Heterocycles; Condensation; Waste prevention; ONE-POT SYNTHESIS; THROUGHPUT SCREENING ASSAY; EFFICIENT SYNTHESIS; APOPTOSIS INDUCERS; IONIC LIQUID; MULTICOMPONENT REACTIONS; 3-COMPONENT SYNTHESIS; 4H-PYRAN SCAFFOLDS; METAL-FREE; CATALYST;
D O I
10.1007/s11030-020-10092-4
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
This paper presents the efficient synthesis of 2-amino-4H-benzo[b]pyrans using mesoporous poly-melamine-formaldehyde as a polymeric heterogeneous catalyst. According to the principals of green chemistry, the reaction was performed by the planetary ball milling process at ambient and neat conditions. The heterogeneous catalyst could be reused up to five runs with no reducing of catalytic efficiency. A variety of substituted 2-amino-4H-benzo[b]pyrans were obtained in good to excellent yields under eco-friendly conditions. Other advantages of the current methodology include short reaction time, wide substrate-scope, and use of a metal-free polymeric catalyst. Also, the current method avoids the use of hazardous reagents and solvents, tedious workup and multi-step purification. This work revealed that porous organic polymers containing Lewis base sites having acceptor-donner hydrogen bonding functional groups, and high porosity could play a vital role in the promotion of the one-pot multicomponent reactions in the solid-phase synthesis. [GRAPHICS] .
引用
收藏
页码:323 / 332
页数:10
相关论文
共 9 条
  • [1] Application of nitrogen-rich porous organic polymer for the solid-phase synthesis of 2-amino-4H-benzo[b]pyran scaffolds using ball milling process
    Lia Zaharani
    Nader Ghaffari Khaligh
    Taraneh Mihankhah
    Mohd Rafie Johan
    Molecular Diversity, 2021, 25 : 323 - 332
  • [2] Facile route for the synthesis and cytotoxic effect of 2-amino-4H-benzo[b]pyran derivatives in aqueous media using copper oxide nanoparticles decorated on cellulose nanocrystals as heterogeneous catalyst
    Thanaraj, Clarina
    Dharsini, G. R. Priya
    Ananthan, Neela
    Velladurai, Rama
    INORGANIC AND NANO-METAL CHEMISTRY, 2019, 49 (09) : 313 - 321
  • [3] Solid-phase synthesis of arylidene and alkylidene malonates, as versatile intermediates, catalyzed using mesoporous poly-melamine-formaldehyde as a nitrogen-rich porous organic polymer (POP)
    Khaligh, Nader Ghaffari
    Gorjian, Hayedeh
    Fahim, Hoda
    Titinchi, Salam J. J.
    RESEARCH ON CHEMICAL INTERMEDIATES, 2021, 47 (09) : 3529 - 3536
  • [4] Solid-phase synthesis of arylidene and alkylidene malonates, as versatile intermediates, catalyzed using mesoporous poly-melamine–formaldehyde as a nitrogen-rich porous organic polymer (POP)
    Nader Ghaffari Khaligh
    Hayedeh Gorjian
    Hoda Fahim
    Salam J. J. Titinchi
    Research on Chemical Intermediates, 2021, 47 : 3529 - 3536
  • [5] Green and Solid-Phase Synthesis of New Dihydro-[1,2,4]Triazolo[1,5-a]Pyrimidine Scaffolds by Using Poly-Melamine-Formaldehyde as a Nitrogen-Rich Porous Organocatalyst
    Khaligh, Nader Ghaffari
    Mihankhah, Taraneh
    POLYCYCLIC AROMATIC COMPOUNDS, 2022, 42 (03) : 942 - 950
  • [6] Grinding Synthesis of 2-Amino-4H-benzo[b]pyran Derivatives Catalyzed By Highly Efficient GPTMS/Guanidine Protected Magnetic Nanoparticles**
    Taherkhani, Hooman
    Ramazani, Ali
    Sajjadifar, Sami
    Aghahosseini, Hamideh
    Rezaei, Aram
    Rezayati, Sobhan
    CHEMISTRYSELECT, 2021, 6 (41): : 11362 - 11374
  • [7] Recyclable mesalamine-functionalized magnetic nanoparticles (mesalamine/GPTMS@SiO2@Fe3O4) for tandem Knoevenagel-Michael cyclocondensation: grinding technique for the synthesis of biologically active 2-amino-4H-benzo[b]pyran derivatives
    Partovi, Mahdiyeh
    Rezayati, Sobhan
    Ramazani, Ali
    Ahmadi, Yavar
    Taherkhani, Hooman
    RSC ADVANCES, 2023, 13 (48) : 33566 - 33587
  • [8] Efficient atom-economical solvent-free one-pot multicomponent synthesis of 2-amino-4H-benzo[b]pyrans catalyzed by solid base SiO2-OK as a reusable catalyst
    Chandralekha, Elangovann
    Thangamani, Arumugam
    Valliappan, Ramiah
    RESEARCH ON CHEMICAL INTERMEDIATES, 2015, 41 (04) : 1951 - 1966
  • [9] Solid-phase synthesis of 4H-2-(3-hydroxy-4-methoxyphenyl)naphtho[1,2-b]pyran-1-one
    Cironi, P
    Albericio, F
    Alvarez, M
    TETRAHEDRON LETTERS, 2004, 45 (39) : 7311 - 7314