Efficient synthesis of halo indanones via chlorosulfonic acid mediated Friedel-Crafts cyclization of aryl propionic acids and their use in alkylation reactions

被引:27
|
作者
Sharma, Anil K. [1 ]
Subramani, Amutha V. [1 ]
Gorman, Christopher B. [1 ]
机构
[1] N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
基金
美国国家科学基金会;
关键词
D O I
10.1016/j.tet.2006.10.065
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Several halo indanones were synthesized from benzyl Meldrum's acid derivatives in two steps. Although several Lewis acids are effective for the Friedel-Crafts ring-closing reaction on more electron-rich arenes, in the case of the electron-deficient arenes this chemistry is not efficient. Here it is reported that chlorosulfonic acid (used as solvent) is an efficient reagent for cyclization of electron-withdrawing arenes. These molecules are potentially useful for subsequent alkylation reactions. The selective alkylation of 5,7-dibromo. indanone is demonstrated using Pd-catalyzed Grignard coupling to provide monoalkylated indanone in good yield. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:389 / 395
页数:7
相关论文
共 50 条
  • [1] The influence of alkylation on the reactions of acid derivatives in the Friedel-Crafts synthesis
    Rothstein, E
    Saboor, MA
    JOURNAL OF THE CHEMICAL SOCIETY, 1943, : 425 - 429
  • [2] Synthesis of tetralone and indanone derivatives via cascade reductive Friedel-Crafts alkylation/cyclization of keto acids/esters
    Yadav, Naveen
    Mahato, Rina
    Khan, Jabir
    Jaiswal, Harshit
    Hazra, Chinmoy Kumar
    CHEMICAL COMMUNICATIONS, 2024, 60 (69) : 9274 - 9277
  • [3] SYNTHESIS OF ARYL ALKYL AND ARYL VINYL SULFONES VIA FRIEDEL-CRAFTS REACTIONS OF SULFONYL FLUORIDES
    HYATT, JA
    WHITE, AW
    SYNTHESIS-STUTTGART, 1984, (03): : 214 - 217
  • [4] ARYL EXCHANGE VIA REVERSIBLE FRIEDEL-CRAFTS REACTION IN THE SYNTHESIS OF A DIARYLACETIC ACID
    NADLER, EB
    RAPPOPORT, Z
    JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (22): : 5361 - 5363
  • [5] Catalytic Friedel-Crafts Alkylation of Electron Rich Aromatic Derivatives with α-Aryl Diazoacetates Mediated by Bronsted Acids
    Gallo, Rafael D. C.
    Momo, Patricia B.
    Day, David P.
    Burtoloso, Antonio C. B.
    ORGANIC LETTERS, 2020, 22 (06) : 2339 - 2343
  • [6] Boric Acid-Mediated Mild and Efficient Friedel-Crafts Alkylation of Indoles with Nitro Styrenes
    Meshram, H. M.
    Rao, N. Nageswara
    Kumar, G. Santosh
    SYNTHETIC COMMUNICATIONS, 2010, 40 (23) : 3496 - 3500
  • [7] Synthesis of Fluorene Derivatives Via TfOH-catalyzed Intramolecular Friedel-Crafts Alkylation Reactions
    Zhou, Ziyang
    Yi, Ying
    Zhang, Fanglin
    Xu, Wengang
    Lu, Zhi
    Luo, Tian
    JOURNAL OF WUHAN UNIVERSITY OF TECHNOLOGY-MATERIALS SCIENCE EDITION, 2023, 38 (05): : 1184 - 1189
  • [8] Synthesis of Fluorene Derivatives Via TfOH-catalyzed Intramolecular Friedel-Crafts Alkylation Reactions
    Ziyang Zhou
    Ying Yi
    Fanglin Zhang
    Wengang Xu
    Zhi Lu
    Tian Luo
    Journal of Wuhan University of Technology-Mater. Sci. Ed., 2023, 38 : 1184 - 1189
  • [9] Synthesis of Fluorene Derivatives Via TfOH-catalyzed Intramolecular Friedel-Crafts Alkylation Reactions
    周子杨
    易英
    ZHANG Fanglin
    XU Wengang
    LU Zhi
    LUO Tian
    JournalofWuhanUniversityofTechnology(MaterialsScience), 2023, 38 (05) : 1184 - 1189
  • [10] Metallocenium Lewis Acid Catalysts for Use in Friedel-Crafts Alkylation and Diels-Alder Reactions
    Blechschmidt, Daniel R.
    Lovstedt, Alex
    Kass, Steven R.
    ORGANOMETALLICS, 2022, 41 (18) : 2648 - 2655