Successful Baylis−Hillman Reaction of Acrylamide with Aromatic Aldehydes

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Abstract

Acrylamide and aromatic aldehydes were found to undergo the Baylis−Hillman reaction at ambient temperature in an aqueous medium in the presence of a stoichiometric amount of base catalyst, DABCO, to give the corresponding 3-hydroxy-2-methylenepropionamides in 61−99% yield. A faster competing, but reverible, non-Baylis−Hillman reaction was initially observed under the conditions to form N-acylhemiaminals, which later disappeared, as the desired Baylis−Hillman adduct was formed as the major product over an extended period of time (12−48 h). This represents the first demonstration of the Baylis−Hillman reaction of aldehydes with acrylamides, which were thought to be inert under atmospheric pressure and at ambient temperature.

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This article has been cited by 16 ACS Journal articles (5 most recent appear below).

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  Solvent-Dependent Reactions for the Synthesis of β-Keto-Benzo-δ-Sultone Scaffolds via DBU-Catalyzed O-Sulfonylation/Intramolecular Baylis–Hillman/1,3-H Shift or Dehydration Tandem Sequences

  Mehdi Ghandi, Abolfazl Hasani Bozcheloei, Seyed Hadi Nazari, and Masoud Sadeghzadeh
  The Journal of Organic Chemistry2011 76 (24), 9975-9982

  • Solvent-Dependent Reactions for the Synthesis of β-Keto-Benzo-δ-Sultone Scaffolds via DBU-Catalyzed O-Sulfonylation/Intramolecular Baylis–Hillman/1,3-H Shift or Dehydration Tandem Sequences

    Mehdi Ghandi, Abolfazl Hasani Bozcheloei, Seyed Hadi Nazari, and Masoud Sadeghzadeh
    The Journal of Organic Chemistry2011 76 (24), 9975-9982

    We have developed a solvent-dependent method for the synthesis of novel benzo-δ-sultone scaffolds. A variety of benzylbenzo[e][1,2]oxathiin-4(3H)-one-2,2-dioxides were obtained in high yields in DMF using a one-pot, DBU-catalyzed condensation of 2-...

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  Highly Chemoselective Baylis−Hillman and Aldol Reactions of 2H-Thiopyran-4(3H)-one Using Tertiary Amine Catalysts in Aqueous Media

  Bagher Eftekhari-Sis, Ali Akbari, and Klaus Harms
  Organic Letters2010 12 (20),

  • Highly Chemoselective Baylis−Hillman and Aldol Reactions of 2H-Thiopyran-4(3H)-one Using Tertiary Amine Catalysts in Aqueous Media

    Bagher Eftekhari-Sis, Ali Akbari, and Klaus Harms
    Organic Letters2010 12 (20),

    For the first time, the Baylis−Hillman (BH) reaction of 2H-thiopyran-4(3H)-one is investigated, and surprisingly, the reaction of 2H-thiopyran-4(3H)-one with aldehydes in the presence of different tertiary amines shows excellent chemo- and ...

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• 

  Solubility of Ethanamide and 2-Propenamide in Supercritical Carbon Dioxide. Measurements and Correlation

  José P. Coelho, Karolina Bernotaityte, Marisa A. Miraldes, Andreia F. Mendonça and Roumiana P. Stateva
  Journal of Chemical & Engineering Data2009 54 (9), 2546-2549

  • Solubility of Ethanamide and 2-Propenamide in Supercritical Carbon Dioxide. Measurements and Correlation

    José P. Coelho, Karolina Bernotaityte, Marisa A. Miraldes, Andreia F. Mendonça and Roumiana P. Stateva
    Journal of Chemical & Engineering Data2009 54 (9), 2546-2549

    Solubilities of ethanamide (acetamide) and 2-propenamide (acrylamide) in supercritical carbon dioxide were measured at T = (308.2, 318.2, and 333.2) K over the pressure range (9.0 to 40.0) MPa by a flow-type apparatus. The solubility of acetamide (2.3·10−...

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• 

  Mechanism of the Morita−Baylis−Hillman Reaction:  A Computational Investigation

  Raphaël Robiette, Varinder K Aggarwal, and Jeremy N. Harvey
  Journal of the American Chemical Society2007 129 (50), 15513-15525

  • Mechanism of the Morita−Baylis−Hillman Reaction:  A Computational Investigation

    Raphaël Robiette, Varinder K Aggarwal, and Jeremy N. Harvey
    Journal of the American Chemical Society2007 129 (50), 15513-15525

    Accurate calculations are presented on the mechanism of the MBH reaction, focusing on the reaction between methyl acrylate and benzaldehyde, catalyzed by a tertiary amine. We address the mechanism under protic solvent-free conditions, but also consider ...

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• 

  The Baylis−Hillman Acetates as a Valuable Source for One-Pot Multistep Synthesis:  A Facile Synthesis of Functionalized Tri-/Tetracyclic Frameworks Containing Azocine Moiety

  Deevi Basavaiah and Kunche Aravindu
  Organic Letters2007 9 (13), 2453-2456

  • The Baylis−Hillman Acetates as a Valuable Source for One-Pot Multistep Synthesis:  A Facile Synthesis of Functionalized Tri-/Tetracyclic Frameworks Containing Azocine Moiety

    Deevi Basavaiah and Kunche Aravindu
    Organic Letters2007 9 (13), 2453-2456

    The Baylis-Hillman acetates have been conveniently transformed into tri-/tetracyclic heterocyclic frameworks containing an important azocine moiety via one-pot multistep protocol involving alkylation, reduction, and cyclization sequence.

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