Efficient Synthesis of Biomass-Derived N-Substituted 2-Hydroxymethyl-5-Methyl-Pyrroles in Two Steps from 5-Hydroxymethylfurfural

被引:24
|
作者
Wozniak, Bartosz [1 ]
Li, Yuehui [2 ]
Hinze, Sandra [1 ]
Tin, Sergey [1 ]
de Vries, Johannes G. [1 ]
机构
[1] Univ Rostock, Leibniz Inst Katalyse, Albert Einstein Str 29a, D-18059 Rostock, Germany
[2] Chinese Acad Sci, State Key Lab Oxo Synth & Select Oxidat, Suzhou Res Inst LICP, LICP, Lanzhou 730000, Gansu, Peoples R China
关键词
Pyrroles; Paal-Knorr synthesis; Heterocycles; Cyclization; Renewable resources; PAAL-KNORR REACTION; CATALYTIC CONVERSION; PYRROLE; LIGANDS; DERIVATIVES; COMPLEXES;
D O I
10.1002/ejoc.201800171
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient two-step synthesis for the conversion of biomass-derived 5-hydroxymethyl-furfural (HMF) to a variety of N-substituted 2-hydroxymethyl-5-methylpyrroles was developed. In the first step, 1-hydroxyhexane-2,5-dione (HHD) was obtained by hydrogenation of HMF and thereafter used in a Paal-Knorr reaction with a range of amines in the absence of catalyst at room temperature. The reaction could potentially be used as a click reaction.
引用
收藏
页码:2009 / 2012
页数:4
相关论文
共 50 条
  • [31] Renewable Production of Nylon-6,6 Monomers from Biomass-Derived 5-Hydroxymethylfurfural (HMF)
    Wang, Tianfu
    Ide, Matthew S.
    Nolan, Michael R.
    Davis, Robert J.
    Shanks, Brent H.
    ENERGY AND ENVIRONMENT FOCUS, 2016, 5 (01) : 13 - 17
  • [32] Purification of Biomass-Derived 5-Hydroxymethylfurfural and Its Catalytic Conversion to 2,5-Furandicarboxylic Acid
    Yi, Guangshun
    Teong, Siew Ping
    Li, Xiukai
    Zhang, Yugen
    CHEMSUSCHEM, 2014, 7 (08) : 2131 - 2135
  • [33] Highly efficient production of 2,5-dihydroxymethylfuran from biomass-derived 5-hydroxymethylfurfural over an amorphous and mesoporous zirconium phosphonate catalyst
    Lei Hu
    Ning Li
    Xiaoli Dai
    Yuqi Guo
    Yetao Jiang
    Aiyong He
    Jiaxing Xu
    Journal of Energy Chemistry , 2019, (10) : 82 - 92
  • [34] Efficient Preparation of Liquid Fuel 2,5-Dimethylfuran from Biomass-Derived 5-Hydroxymethylfurfural over Ru-NaY Catalyst
    Nagpure, Atul S.
    Lucas, Nishita
    Chilukuri, Satyanarayana V.
    ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2015, 3 (11): : 2909 - 2916
  • [35] Highly efficient production of 2,5-dihydroxymethylfuran from biomass-derived 5-hydroxymethylfurfural over an amorphous and mesoporous zirconium phosphonate catalyst
    Hu, Lei
    Li, Ning
    Dai, Xiaoli
    Guo, Yuqi
    Jiang, Yetao
    He, Aiyong
    Xu, Jiaxing
    JOURNAL OF ENERGY CHEMISTRY, 2019, 37 : 82 - 92
  • [36] Biomass-derived 5-hydroxymethylfurfural (HMF) and 2,5-dimethylfuran (DMF) synthesis as promising alternative fuel: A prospective review
    Mehta, Jigesh
    V. Metre, Anand
    Bhakhar, Mathurkumar S.
    Panwar, D. S.
    Dharaskar, Swapnil
    MATERIALS TODAY-PROCEEDINGS, 2022, 62 (P13) : 6978 - 6984
  • [37] Catalytic conversion of biomass-derived 5-hydroxymethylfurfural to 5-hydroxymethyl-2-furancarboxylic acid using novel cobalt-based MOF in the presence of deep eutectic solvents
    Ashrafi, Samaneh Sedigh
    Maleki, Behrooz
    SCIENTIFIC REPORTS, 2024, 14 (01):
  • [38] Alloy-Driven Efficient Electrocatalytic Oxidation of Biomass-Derived 5-Hydroxymethylfurfural towards 2,5-Furandicarboxylic Acid: A Review
    Guo, Mengyan
    Lu, Xuebin
    Xiong, Jian
    Zhang, Rui
    Li, Xiaoyun
    Qiao, Yina
    Ji, Na
    Yu, Zhihao
    CHEMSUSCHEM, 2022, 15 (17)
  • [39] Efficient aerobic oxidation of biomass-derived 5-hydroxymethylfurfural to 2,5-diformylfuran catalyzed by magnetic nanoparticle supported manganese oxide
    Liu, Bing
    Zhang, Zehui
    Lv, Kangle
    Deng, Kejian
    Duan, Hongmin
    APPLIED CATALYSIS A-GENERAL, 2014, 472 : 64 - 71
  • [40] A unique Co@CoO catalyst for hydrogenolysis of biomass-derived 5-hydroxymethylfurfural to 2,5-dimethylfuran
    Xiang, Shuang
    Dong, Lin
    Wang, Zhi-Qiang
    Han, Xue
    Daemen, Luke L.
    Li, Jiong
    Cheng, Yongqiang
    Guo, Yong
    Liu, Xiaohui
    Hu, Yongfeng
    Ramirez-Cuesta, Anibal J.
    Yang, Sihai
    Gong, Xue-Qing
    Wang, Yanqin
    NATURE COMMUNICATIONS, 2022, 13 (01)