Expeditious Microwave-Assisted Thionation with the System PSCl₃/H₂O/Et₃N under Solvent-Free Condition

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Abstract

A novel thionation protocol for carbonyl compounds, with the system PSCl₃/H₂O/Et₃N has been discovered. Clean, rapid, and efficient synthesis of a variety of thiocarbonyl compounds such as thioamides, thiolactams, thioketones, thioxanthones, and thioacridone can be achieved through this simple and convenient method under solventless condition with microwave irradiation.

Citing Articles

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This article has been cited by 3 ACS Journal articles (3 most recent appear below).

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  Thionations Using a P₄S₁₀−Pyridine Complex in Solvents Such as Acetonitrile and Dimethyl Sulfone

  Jan Bergman, Birgitta Pettersson, Vedran Hasimbegovic, and Per H. Svensson
  The Journal of Organic Chemistry2011 76 (6), 1546-1553

  • Thionations Using a P₄S₁₀−Pyridine Complex in Solvents Such as Acetonitrile and Dimethyl Sulfone

    Jan Bergman, Birgitta Pettersson, Vedran Hasimbegovic, and Per H. Svensson
    The Journal of Organic Chemistry2011 76 (6), 1546-1553

    Tetraphosphorus decasulfide (P4S10) in pyridine has been used as a thionating agent for a long period of time. The moisture-sensitive reagent has now been isolated in crystalline form, and the detailed structure has been determined by X-ray ...

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

  Direct Formation of Ring-Fused 1,3-Thiazine-2,4-dithiones from Aromatic o-Amino Carboxylic Acids: Observation of a Carbon Disulfide Mediated Thionation

  Philipp A. Ottersbach, Paul W. Elsinghorst, Hans-Georg Häcker and Michael Gütschow
  Organic Letters2010 12 (16), 3662-3665

  • Direct Formation of Ring-Fused 1,3-Thiazine-2,4-dithiones from Aromatic o-Amino Carboxylic Acids: Observation of a Carbon Disulfide Mediated Thionation

    Philipp A. Ottersbach, Paul W. Elsinghorst, Hans-Georg Häcker and Michael Gütschow
    Organic Letters2010 12 (16), 3662-3665

    A facile synthesis of 2H-3,1-benzothiazine-2,4(1H)-dithiones (trithioisatoic anhydrides) or 2H-naphtho[2,3-d][1,3]thiazine-2,4(1H)-dithione solely from anthranilic acids or 3-amino-2-naphthoic acid and carbon disulfide, performed at room temperature in ...

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

  Direct Thionation and Selenation of Amides Using Elemental Sulfur and Selenium and Hydrochlorosilanes in the Presence of Amines

  Fumitoshi Shibahara, Rie Sugiura and Toshiaki Murai
  Organic Letters2009 11 (14), 3064-3067

  • Direct Thionation and Selenation of Amides Using Elemental Sulfur and Selenium and Hydrochlorosilanes in the Presence of Amines

    Fumitoshi Shibahara, Rie Sugiura and Toshiaki Murai
    Organic Letters2009 11 (14), 3064-3067

    Reactions of amides with elemental sulfur in the presence of hydrochlorosilanes and amines give the corresponding thioamides in good to high yields. The process takes place via reduction of elemental sulfur by the hydrochlorosilane in the presence of a ...

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

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