SYNTHESIS OF FURAN-OXAZOLE CONJUGATED FLUORESCENT MATERIALS FROM BIOMASS-DERIVED FURFURAL THROUGH CROSS-COUPLING REACTIONS

被引:5
|
作者
Murase, Yuki [1 ]
Ashida, Kana [1 ]
Tanaka, Shota [1 ]
Okano, Kentaro [1 ]
Mori, Atsunori [1 ]
机构
[1] Kobe Univ, Dept Chem Sci & Engn, 1-1 Nada, Kobe, Hyogo 6578501, Japan
关键词
Furfural; L-Serine; Cross-Coupling Reaction; pi-Conjugation; Photoluminescence; C-H BOND; HETEROAROMATIC-COMPOUNDS; LIGNOCELLULOSIC BIOMASS; ORGANIC SEMICONDUCTORS; BIODIESEL PRODUCTION; ARYLATION; BIOFUELS; PLATFORM; DESIGN; ACID;
D O I
10.3987/COM-15-S(T)9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Synthesis of furyloxazole was performed from biomass-derived furfural and senile methyl ester through dehydrative condensation and oxidation in one pot. Bromination and subsequent palladium-catalyzed arylation with arylboronates proceeded smoothly at the furan ring to provide arylated furylthiazoles. Arylation of C-H bond at the 5 position of the oxazole ring under Fagnou's conditions led to formation of diarylated furyloxazoles, which exhibit higher quantum yields over those of the related furylthiazole derivatives.
引用
收藏
页码:140 / 149
页数:10
相关论文
共 50 条
  • [1] Preparation of Fluorescent Materials from Biomass-Derived Furfural and Natural Amino Acid Cysteine through Cross-Coupling Reactions for Extended π-Conjugation
    Tanaka, Shota
    Ashida, Kana
    Tatsuta, Go
    Mori, Atsunori
    SYNLETT, 2015, 26 (11) : 1496 - 1500
  • [2] Green Synthesis of Fluorescent Peptidomimetic Triazoles from Biomass-Derived 5-(Chloromethyl)furfural
    Salim, Kunnummal Mangott Muhammed
    Shamsiya, Aranhikkal
    Damodaran, Bahulayan
    CHEMISTRYSELECT, 2018, 3 (39): : 11141 - 11146
  • [3] Synthesis of anti-inflammatory furan fatty acids from biomass-derived 5-(chloromethyl)furfural
    Chang, Fei
    Hsu, Wan-Hsuan
    Mascal, Mark
    SUSTAINABLE CHEMISTRY AND PHARMACY, 2015, 1 : 14 - 18
  • [4] Biomass-derived solvents as effective media for cross-coupling reactions and C-H functionalization processes
    Santoro, Stefano
    Ferlin, Francesco
    Luciani, Lorenzo
    Ackermann, Lutz
    Vaccaro, Luigi
    GREEN CHEMISTRY, 2017, 19 (07) : 1601 - 1612
  • [5] Synthesis of Renewable meta-Xylylenediamine from Biomass-Derived Furfural
    Scodeller, Ivan
    Mansouri, Samir
    Morvan, Didier
    Muller, Eric
    Vigier, Karine de Oliveira
    Wischert, Raphael
    Jerome, Francois
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (33) : 10510 - 10514
  • [6] Synthesis of Substituted Cyclooctenes through Cross-Coupling Reactions
    Murata, Ryuichi
    Yoshida, Rakuto
    Uraguch, Daisuke
    Asano, Keisuke
    SYNLETT, 2025, 36 (01) : 69 - 74
  • [7] Synthesis of π-conjugated systems bearing thiophene and pyrrole heterocycles through palladium catalyzed cross-coupling reactions
    Castro, M. Cidalia R.
    Raposo, M. Manuela M.
    TETRAHEDRON, 2016, 72 (15) : 1881 - 1887
  • [8] Waste biomass-derived carbon-supported palladium-based catalyst for cross-coupling reactions and energy storage applications
    Kempasiddaiah, Manjunatha
    Raj, K. A. Sree
    Kandathil, Vishal
    Dateer, Ramesh B.
    Sasidhar, B. S.
    Yelamaggad, C. V.
    Rout, Chandra Sekhar
    Patil, Siddappa A.
    APPLIED SURFACE SCIENCE, 2021, 570
  • [9] Valorisation of urban waste to access low-cost heterogeneous palladium catalysts for cross-coupling reactions in biomass-derived γ-valerolactone
    Valentini, Federica
    Ferlin, Francesco
    Lilli, Simone
    Marrocchi, Assunta
    Ping, Liu
    Gu, Yanlong
    Vaccaro, Luigi
    GREEN CHEMISTRY, 2021, 23 (16) : 5887 - 5895