Conversion of 2-Alkylcinnamaldehydes to 2-Alkylindanones via a Catalytic Intramolecular Friedel−Crafts Reaction

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Abstract

The preparation of indanones by the intramolecular acylation of 3-arylpropanoic acids or halides requires the use of noncatalytic acid promoters. In the presence of 5−10 mol % FeCl₃, in situ generated dimethyl acetals of (E)-2-alkylcinnamaldehydes cyclize to 1-methoxy-2-alkyl-1H-indenes in good-to-high yields. The 1-methoxyindenes were converted in high yield into 2-alkylindanones by treatment with triethylamine, to effect isomerization to the isomeric enol ethers, followed by acid-catalyzed hydrolysis. Thus, a catalytic, intramolecular Friedel−Crafts reaction leading to 2-alkylindanones from 2-alkylcinnamaldehydes was developed.

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This article has been cited by 4 ACS Journal articles (4 most recent appear below).

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  Lewis Acid Promoted Reactions of Ethenetricarboxylates with Allenes: Synthesis of Indenes and γ-Lactones via Conjugate Addition/Cyclization Reaction

  Shoko Yamazaki, Yuko Yamamoto, Yugo Fukushima, Masachika Takebayashi, Tetsuma Ukai and Yuji Mikata
  The Journal of Organic Chemistry2010 75 (15), 5216-5222

  • Lewis Acid Promoted Reactions of Ethenetricarboxylates with Allenes: Synthesis of Indenes and γ-Lactones via Conjugate Addition/Cyclization Reaction

    Shoko Yamazaki, Yuko Yamamoto, Yugo Fukushima, Masachika Takebayashi, Tetsuma Ukai and Yuji Mikata
    The Journal of Organic Chemistry2010 75 (15), 5216-5222

    Indenes are important core structures in organic chemistry. Few simple arylallenes have been used to construct indene skeletons by Friedel−Crafts reaction. Lewis acid catalyzed reaction of ethenetricarboxylates 1 and arylallenes has been examined in this ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Preparation of Trifluoromethylated Dihydrocoumarins, Indanones, and Arylpropanoic Acids by Tandem Superacidic Activation of 2-(Trifluoromethyl)acrylic Acid with Arenes

  G. K. Surya Prakash, Farzaneh Paknia, Habiba Vaghoo, Golam Rasul, Thomas Mathew and George A. Olah
  The Journal of Organic Chemistry2010 75 (7), 2219-2226

  • Preparation of Trifluoromethylated Dihydrocoumarins, Indanones, and Arylpropanoic Acids by Tandem Superacidic Activation of 2-(Trifluoromethyl)acrylic Acid with Arenes

    G. K. Surya Prakash, Farzaneh Paknia, Habiba Vaghoo, Golam Rasul, Thomas Mathew and George A. Olah
    The Journal of Organic Chemistry2010 75 (7), 2219-2226

    Indanones and coumarins are important intermediates for the convenient synthesis of many pharmaceutical and biologically active compounds. Fluoroorganics play a vital role in the design of very effective therapeutics due to significant enhancenment in ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Indanones and Indenols from 2-Alkylcinnamaldehydes via the Intramolecular Friedel−Crafts Reaction of Geminal Diacetates

  Gary B. Womack, John G. Angeles, Vincent E. Fanelli, Brinda Indradas, Roger L. Snowden and Philippe Sonnay
  The Journal of Organic Chemistry2009 74 (15), 5738-5741

  • Indanones and Indenols from 2-Alkylcinnamaldehydes via the Intramolecular Friedel−Crafts Reaction of Geminal Diacetates

    Gary B. Womack, John G. Angeles, Vincent E. Fanelli, Brinda Indradas, Roger L. Snowden and Philippe Sonnay
    The Journal of Organic Chemistry2009 74 (15), 5738-5741

    When treated with Ac2O at rt in the presence of 4−6 mol % FeCl3, 2-alkylcinnamaldehydes are converted to 2-alkyl-1H-inden-1-yl acetates through the intermediacy of gem-diacetates. Methanolysis of the indenyl acetates yields the corresponding indenols. ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Mild, Efficient Friedel−Crafts Acylations from Carboxylic Acids Using Cyanuric Chloride and AlCl₃

  Cyrous O. Kangani and Billy W. Day
  Organic Letters2008 10 (13), 2645-2648

  • Mild, Efficient Friedel−Crafts Acylations from Carboxylic Acids Using Cyanuric Chloride and AlCl₃

    Cyrous O. Kangani and Billy W. Day
    Organic Letters2008 10 (13), 2645-2648

    A mild method for Friedel−Crafts acylation with aromatic and aliphatic carboxylic acids using cyanuric chloride, pyridine, and AlCl3 was developed. Both inter- and intramolecular acylations were achieved at room temperature in high yield and in very ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links

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