Efficient Synthesis of Diarylmethylamines via Lewis Acid Catalyzed Friedel-Crafts Reactions of Donor-Acceptor Aziridines with N,N-Dialkylanilines

被引:5
|
作者
Kim, Yerin [1 ]
Kwon, Yong Il [1 ]
Kim, Sung-Gon [1 ]
机构
[1] Kyonggi Univ, Dept Chem, 154-42 Gwanggyosan Ro, Suwon 16227, South Korea
来源
SYNTHESIS-STUTTGART | 2020年 / 52卷 / 02期
基金
新加坡国家研究基金会;
关键词
diarylmethylamine; Friedel-Crafts reaction; donor-acceptor aziridine; N; N-dialkylaniline; Lewis acid; ASYMMETRIC 3+2 CYCLOADDITION; CHIRAL DIENE LIGANDS; H BOND ARYLATION; N-TOSYLAZIRIDINES; C-ARYLATION; N; N-DIALKYL-3-VINYLANILINES; DERIVATIVES; FUNCTIONALIZATION; TOSYLARYLIMINES; ALDEHYDES;
D O I
10.1055/s-0039-1690731
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A method for efficient and mild synthesis of diarylmethylamine scaffold, via Lewis acid catalyzed Friedel-Crafts reaction of donor-acceptor aziridines with N,N-dialkylanilines to afford a biologically important diarylmethylamine derivatives in high yields (up to 88%), is presented. This reaction is suitable for the synthesis of various diarylmethylamine derivatives and has a broad scope for electron-rich arenes, including dimethoxybenzene.
引用
收藏
页码:281 / 289
页数:9
相关论文
共 50 条
  • [31] Synthesis of Indazolones via Friedel-Crafts Cyclization of Blocked (Masked) N-Isocyanates
    Elkaeed, Eslam B.
    An, Jing
    Beauchemin, Andre M.
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (18): : 9890 - 9897
  • [32] Highly regioselective Friedel-Crafts reactions of electron-rich aromatic compounds with pyruvate catalyzed by Lewis acid-base: Efficient synthesis of pesticide cycloprothrin
    Si, Yu-Gui
    Chen, Jun
    Li, Fan
    Li, Jin-Hua
    Qin, Ye-Jun
    Jiang, Biao
    ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (7-8) : 898 - 904
  • [33] Tunable Titanocene Lewis Acid Catalysts for Selective Friedel-Crafts Reaction of Indoles and N-Sulfonylaldimines
    Wang, Xiu
    Wang, Zhenhua
    Zhang, Guofang
    Zhang, Weiqiang
    Wu, Ya
    Gao, Ziwei
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (03) : 502 - 507
  • [34] Lewis and Bronsted acid catalyzed Friedel-Crafts hydroxyalkylation of mucohalic acids:: a facile synthesis of functionalized γ-aryl γ-butenolides
    Zhang, Ji
    Blazecka, Peter G.
    Curran, Timothy T.
    TETRAHEDRON LETTERS, 2007, 48 (14) : 2611 - 2615
  • [35] One-Pot Synthesis of N-(Phosphorylmethyl)Pyrrolidines via Acid-Catalyzed Cascade Elimination/Cyclization/Friedel-Crafts Reaction
    Vagapova, Liliya, I
    Burilov, Alexander R.
    Gazizov, Almir S.
    Voronina, Julia K.
    Litvinov, Igor A.
    Mahrous, Essan M.
    Virieux, David
    Pirat, Jean-Luc
    Matylitskii, Kiryll, V
    Pudovik, Mikhail A.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2020, 56 (05) : 542 - 547
  • [36] FRIEDEL-CRAFTS REACTIONS .2. AMIDOALKYLATION BY N-ACETOXYMETHYL-N-METHYLFORMAMIDE IN PRESENCE OF TRIFLUOROACETIC-ACID
    NYBERG, K
    ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1974, B 28 (07): : 825 - 826
  • [37] Highly efficient synthesis of 3-indolyl-substituted phthalides via Friedel-Crafts reactions in water
    Lin, Hua
    Sun, Xing-Wen
    TETRAHEDRON LETTERS, 2008, 49 (36) : 5343 - 5346
  • [38] Efficient Lewis acid-assisted Bronsted acid (LBA) catalysis in the iron-catalyzed Friedel-Crafts alkylation reaction of indoles
    Jiang, Zhen-Yu
    Wu, Ji-Rong
    Li, Li
    Chen, Xi-Huai
    Lai, Guo-Qiao
    Jiang, Jian-Xiong
    Lu, Yixin
    Xu, Li-Wen
    CENTRAL EUROPEAN JOURNAL OF CHEMISTRY, 2010, 8 (03): : 669 - 673
  • [39] REACTIONS WITH AZIRIDINES .48. FRIEDEL-CRAFTS REACTIONS WITH N-SULFONATED AZIRIDINES AND WITH OPEN-CHAIN SULFONAMIDES - SULFONAMIDES AS LEAVING GROUPS IN OPEN-CHAIN STRUCTURES
    STAMM, H
    ONISTSCHENKO, A
    BUCHHOLZ, B
    MALL, T
    JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (01): : 193 - 199
  • [40] Titanocene Lewis Acid Complexes with Diversified N,O-Ligands: Selectivity toward Three-Component Friedel-Crafts Reactions of Indoles
    Wu, Ya
    Lin, Zhiwei
    Fang, Rongmiao
    Guo, Yingying
    Tu, Li
    Yan, Yikun
    Zhang, Weiqiang
    Sun, Huaming
    Gao, Ziwei
    ORGANOMETALLICS, 2022, 41 (09) : 1067 - 1077