Iron-Catalyzed C(sp3)-C(sp3) Bond Formation in 3,4-Dihydro-1,4-benzoxazin-2-ones

被引:13
作者
Dong, Jie [1 ]
Min, Wenjian [1 ]
Li, Haitao [1 ]
Quan, Zhengjun [1 ]
Yang, Caixia [1 ]
Huo, Congde [1 ]
机构
[1] Northwest Normal Univ, Coll Chem & Chem Engn, Lanzhou 730070, Gansu, Peoples R China
基金
中国国家自然科学基金;
关键词
iron-catalyzed; carbon-carbon bond formation; one electron oxidation; benzoxazinone; dehydrogenative coupling; DEHYDROGENATIVE COUPLING REACTIONS; C-H FUNCTIONALIZATION; TRANSITION-METAL; VISIBLE-LIGHT; HETEROGENEOUS CATALYSIS; MOLECULAR-OXYGEN; GLYCINE DERIVATIVES; ORGANIC-SYNTHESIS; NANOPARTICLES; ELECTRON;
D O I
10.1002/adsc.201700816
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A convenient iron-catalyzed oxidative dehydrogenative coupling reaction of 3,4-Dihydro-1,4-benzoxazin-2-ones with malonic esters or ketones was performed under mild reaction conditions to construct alkyl-alkyl C(sp(3))-C(sp(3)) bonds. This transformation can be catalyzed efficiently by magnetically recoverable iron nanoparticles and the catalyst can be recycled easily for 7 times without decreasing activity.
引用
收藏
页码:3940 / 3944
页数:5
相关论文
共 58 条
  • [1] Perspectives on 1,4-benzodioxins, 1,4-benzoxazines and their 2,3-dihydro derivatives
    Achari, B
    Mandal, SB
    Dutta, PK
    Chowdhury, C
    [J]. SYNLETT, 2004, (14) : 2449 - 2467
  • [2] Nanoparticles as recyclable catalysts: The frontier between homogeneous and heterogeneous catalysis
    Astruc, D
    Lu, F
    Aranzaes, JR
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (48) : 7852 - 7872
  • [3] Pd on surface-modified NiFe2O4 nanoparticles:: A magnetically recoverable catalyst for Suzuki and Heck reactions
    Baruwati, Babita
    Guin, Debanjan
    Manorama, Sunkara V.
    [J]. ORGANIC LETTERS, 2007, 9 (26) : 5377 - 5380
  • [4] Iron Catalysis in Organic Synthesis
    Bauer, Ingmar
    Knoelker, Hans-Joachim
    [J]. CHEMICAL REVIEWS, 2015, 115 (09) : 3170 - 3387
  • [5] CATION RADICAL CYCLO-ADDITIONS AND RELATED SIGMATROPIC REACTIONS
    BAULD, NL
    [J]. TETRAHEDRON, 1989, 45 (17) : 5307 - 5363
  • [6] Amine Functionalization via Oxidative Photoredox Catalysis: Methodology Development and Complex Molecule Synthesis
    Beatty, Joel W.
    Stephenson, Corey R. J.
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (05) : 1474 - 1484
  • [7] Iron nanoparticles in the coupling of alkyl halides with aryl Grignard reagents
    Bedford, RB
    Betham, M
    Bruce, DW
    Davis, SA
    Frost, RM
    Hird, M
    [J]. CHEMICAL COMMUNICATIONS, 2006, (13) : 1398 - 1400
  • [8] REACTIONS OF 19-ETHOXYCARBONYL-19-DEMETHYLVINCADIFFORMINE - SYNTHESIS OF 19-ETHOXYCARBONYL-19-DEMETHYLAPOVINCAMINE
    BELATTAR, A
    SAXTON, JE
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (13): : 1583 - 1585
  • [9] Novel synthesis of 3,4-dihydro-5-bromo[1,4]oxazin-2-one derivatives, new protease inhibitor scaffold
    Bihel, F
    Kraus, JL
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (05) : 793 - 799
  • [10] Iron-catalyzed reactions in organic synthesis
    Bolm, C
    Legros, J
    Le Paih, J
    Zani, L
    [J]. CHEMICAL REVIEWS, 2004, 104 (12) : 6217 - 6254