Diastereoselective Synthesis of Pyranoquinolines on Zirconium Containing UiO-66 Metal-Organic Frameworks

被引:44
|
作者
Rechac, Victor L. [1 ]
Cirujano, Francisco G. [1 ]
Corma, Avelino [1 ]
Llabres i Xamena, Francesc X. [1 ]
机构
[1] Univ Politecn Valencia, Inst Tecnol Quim, Consejo Super Invest Cient, Ave Naranjos S-N, E-46022 Valencia, Spain
关键词
Metal-organic frameworks; Heterogeneous catalysis; Zirconium; Diastereoselectivity; Cycloaddition; Nitrogen heterocycles; DIELS-ALDER REACTIONS; STEREOSELECTIVE-SYNTHESIS; HETEROGENEOUS CATALYST; CONVENIENT SYNTHESIS; ACID; DERIVATIVES; QUINOLINES; EFFICIENT; MOFS;
D O I
10.1002/ejic.201600372
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The Zr terephthalate MOFs UiO-66 and UiO-66-NH2 have been found to be highly diastereoselective catalysts for the synthesis of a pyrano[3,2-c]quinoline through an inverse electron -demand aza-Diels-Alder [4+2] cycloaddition of an aryl Qmine (formed in situ from aniline and benzaldehyde) and 3,4-dihydro-2H-pyran in one pot, affording the corresponding trans isomer in diastereomeric excesses of 90-95 %. The solids are stable under the reaction conditions and can be reused at least three times without significant loss of activity or diastereoselectivity.
引用
收藏
页码:4512 / 4516
页数:5
相关论文
共 50 条
  • [1] An efficient modulated synthesis of zirconium metal-organic framework UiO-66
    Chen, Xia
    Li, Yongjie
    Fu, Qiang
    Qin, Hongyun
    Lv, Junnan
    Yang, Kun
    Zhang, Qicheng
    Zhang, Hui
    Wang, Ming
    [J]. RSC ADVANCES, 2022, 12 (10) : 6083 - 6092
  • [2] Insights into the Spray Synthesis of UiO-66 and UiO-66-NH2 Metal-Organic Frameworks: Effect of Zirconium Precursors and Process Parameters
    Kubo, Masaru
    Miyoshi, Yusuke
    Uchitomi, Yushi
    Shimada, Manabu
    [J]. CRYSTALS, 2024, 14 (02)
  • [3] Microfluidic Synthesis of UiO-66 Metal-organic Frameworks Modified with Different Functional Groups
    Sheng Bingchen
    Li Cong
    Liu Yingya
    Wang Anjie
    Wang Yao
    Zhang Jian
    Liu Weixu
    [J]. CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2019, 40 (07): : 1365 - 1373
  • [4] UiO-66 metal-organic frameworks in water treatment: A critical review
    Ahmadijokani, Farhad
    Molavi, Hossein
    Rezakazemi, Mashallah
    Tajahmadi, Shima
    Bahi, Addie
    Ko, Frank
    Aminabhavi, Tejraj M.
    Li, Jian-Rong
    Arjmand, Mohammad
    [J]. PROGRESS IN MATERIALS SCIENCE, 2022, 125
  • [5] The adsorption properties of defect controlled metal-organic frameworks of UiO-66
    Zhang, Aibo
    Liu, Boyu
    Liu, Moxi
    Xie, Zhiyuan
    Wang, Dong
    Feng, Guona
    [J]. SEPARATION AND PURIFICATION TECHNOLOGY, 2021, 270
  • [6] Computational exploration of newly synthesized zirconium metal-organic frameworks UiO-66,-67,-68 and analogues
    Yang, Li-Ming
    Ganz, Eric
    Svelle, Stian
    Tilset, Mats
    [J]. JOURNAL OF MATERIALS CHEMISTRY C, 2014, 2 (34) : 7111 - 7125
  • [7] Modulated synthesis of zirconium metal-organic framework UiO-66 with enhanced dichloromethane adsorption capacity
    Zhou, Lin
    Zhang, Xinghua
    Chen, Yunlin
    [J]. MATERIALS LETTERS, 2017, 197 : 167 - 170
  • [8] Metal-organic framework UiO-66 membranes
    Xinlei Liu
    [J]. Frontiers of Chemical Science and Engineering, 2020, 14 : 216 - 232
  • [9] Low experimental thermal conductivity of zirconium metal-organic framework UiO-66
    Lai, Hoa Thi
    Tran, Nhat Quang Minh
    Nguyen, Linh Ho Thuy
    Le, Thu Bao Nguyen
    Nguyen, Cuong Chi
    Pham, Anh Tuan Thanh
    Doan, Tan Le Hoang
    Park, Sungkyun
    Hong, Jongill
    Snyder, Gerald Jeffrey
    Phan, Thang Bach
    [J]. APPLIED PHYSICS LETTERS, 2024, 124 (15)
  • [10] Metal-organic framework UiO-66 membranes
    Liu, Xinlei
    [J]. FRONTIERS OF CHEMICAL SCIENCE AND ENGINEERING, 2020, 14 (02) : 216 - 232