Ring-Expansion Reaction of Oximes with Aluminum Reductants

被引：21
|
作者：
Cho, Hidetsura [1 ,2 ]
Iwama, Yusuke [2 ]
Mitsuhashi, Nakako [2 ]
Sugimoto, Kenji [2 ]
Okano, Kentaro [2 ]
Tokuyama, Hidetoshi [2 ]
机构：
[1] Tohoku Univ, Grad Sch Sci, Aoba Ku, Sendai, Miyagi 9808578, Japan
[2] Tohoku Univ, Grad Sch Pharmaceut Sci, Aoba Ku, Sendai, Miyagi 9808578, Japan
来源：
MOLECULES | 2012年 / 17卷 / 06期
关键词：
aluminum reductant; dichloroaluminum hydride (AlHCl2); ring-expansion of oxime; rearrangement of oxime; cyclopentyl methyl ether (CPME); DIISOBUTYLALUMINUM HYDRIDE; REGIOSELECTIVE SYNTHESIS; AROMATIC RING; REDUCTION; HETEROCYCLES; DERIVATIVES; MECHANISM; REAGENT; SOLVENT;
D O I：
10.3390/molecules17067348
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：
The ring-expansion reactions of heterocyclic ketoximes and carbocyclic ketoximes with several reductants such as AlHCl2, AlH3 (alane), LiAlH4, LiAlH((OBu)-Bu-t)(3), and (MeOCH2CH2O)(2)AlH2Na (Red-Al) were examined. Among reductants, AlHCl2 (LiAlH4:AlCl3 = 1:3) in cyclopentyl methyl ether (CPME) has been found to be a suitable reagent for the reaction, and the rearranged cyclic secondary amines were obtained in good to excellent yields.
引用
收藏
页码：7348 / 7355
页数：8
相关论文
共 50 条
  • [31] Photochemical Approach to the Cyclohepta[b]indole Scaffold by Annulative Two-Carbon Ring-Expansion
    Tymann, Dina Christina
    Benedix, Lars
    Iovkova, Lyuba
    Pallach, Roman
    Henke, Sebastian
    Tymann, David
    Hiersemann, Martin
    CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (52) : 11974 - 11978
  • [32] Phenoxaphosphonium Mixed Ylides in Ring Expansion Reaction
    Nenashev, Anton S.
    Dospekhov, Dmitrii A.
    Zavaruev, Mikhail V.
    Levina, Irina I.
    Roznyatovsky, Vitaly A.
    Mironov, Andrey V.
    Pavlova, Anna S.
    Podrugina, Tatyana A.
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (09) : 6533 - 6538
  • [33] Investigating the ring expansion reaction of pentaphenylborole and an azide
    Couchman, Shannon A.
    Thompson, Trevor K.
    Wilson, David J. D.
    Dutton, Jason L.
    Martin, Caleb D.
    CHEMICAL COMMUNICATIONS, 2014, 50 (79) : 11724 - 11726
  • [34] Synthesis of Benzo[b]azocin-2-ones by Aryl Amination and Ring-Expansion of α-(Iodophenyl)-β-oxoesters
    Dierks, Anna
    Toenjes, Jan
    Schmidtmann, Marc
    Christoffers, Jens
    CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (65) : 14912 - 14920
  • [35] Switchable synthesis of natural-product-like lawsones and indenopyrazoles through regioselective ring-expansion of indantrione
    Hu, Bingwei
    Yan, Wenxin
    Jiang, Peiyun
    Jiang, Ling
    Yuan, Xu
    Lin, Jun
    Jiao, Yinchun
    Jin, Yi
    COMMUNICATIONS CHEMISTRY, 2023, 6 (01)
  • [36] Ancillary Ligand Lability Improves Control in Cyclic Ruthenium Benzylidene Initiated Ring-Expansion Metathesis Polymerizations
    Levenson, Adelaide M.
    Morrison, Christine M.
    Huang, Pin-Ruei
    Wang, Teng-Wei
    Carter-Schwendler, Zak
    Golder, Matthew R.
    ACS MACRO LETTERS, 2023, 12 (10) : 1286 - 1292
  • [37] PPh3-Catalyzed Ring-Expansion Reactions of Sulfamate-Derived Cyclic Imines with Acetylenedicarboxylates
    Yang, Zhilin
    Yu, Hao
    Zhang, Lei
    Wei, Hang
    Xiao, Yumei
    Chen, Lanzhen
    Guo, Hongchao
    CHEMISTRY-AN ASIAN JOURNAL, 2014, 9 (01) : 313 - 318
  • [38] Intramolecular C-N Bond Activation and Ring-Expansion Reactions of N-Heterocyclic Carbenes
    Hemberger, Patrick
    Bodi, Andras
    Berthel, Johannes H. J.
    Radius, Udo
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (04) : 1434 - 1438
  • [39] Fabrication and Diverse Ring-Expansion Nanocatalysis of Functionalized Pt-Nanoparticles to a General Synthesis of Pyrrolines: A 3D-Mid-IR Study
    Ghosh, Subhadeep
    Debnath, Sudipto
    Das, Uttam K.
    Maiti, Dilip K.
    INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, 2017, 56 (42) : 12056 - 12069
  • [40] Synthesis of C-furanosides from a D-glucal-derived cyclopropane through a ring-expansion/ring-contraction sequence
    Hewitt, Russell J.
    Harvey, Joanne E.
    CHEMICAL COMMUNICATIONS, 2011, 47 (01) : 421 - 423
12345