催化学报

催化学报 ›› 2014, Vol. 35 ›› Issue (1): 127-133.DOI: 10.1016/S1872-2067(12)60727-X

• 研究论文 • 上一篇    下一篇

Thiourea dioxide: An efficient and reusable organocatalyst for the rapid one-pot synthesis of pyrano[4, 3-b]pyran derivatives in water

Majid Ghashanga, Syed Sheik Mansoorb, Krishnamoorthy Aswinb   

  1. a Faculty of Sciences, Najafabad Branch, Islamic Azad University, Najafabad, Esfahan, Iran;
    b Research Department of Chemistry, Bioactive Organic Molecule Synthetic Unit, C. Abdul Hakeem College, Melvisharam - 632 509, Tamil Nadu, India
  • 收稿日期:2013-08-09 修回日期:2013-10-09 出版日期:2013-12-23 发布日期:2014-01-17
  • 通讯作者: Syed Sheik Mansoor

Thiourea dioxide: An efficient and reusable organocatalyst for the rapid one-pot synthesis of pyrano[4, 3-b]pyran derivatives in water

Majid Ghashanga, Syed Sheik Mansoorb, Krishnamoorthy Aswinb   

  1. a Faculty of Sciences, Najafabad Branch, Islamic Azad University, Najafabad, Esfahan, Iran;
    b Research Department of Chemistry, Bioactive Organic Molecule Synthetic Unit, C. Abdul Hakeem College, Melvisharam - 632 509, Tamil Nadu, India
  • Received:2013-08-09 Revised:2013-10-09 Online:2013-12-23 Published:2014-01-17
  • Contact: Syed Sheik Mansoor
  • Supported by:

    This work was supported by Research Department of Chemistry, C. Abdul Hakeem College, Melvisharam - 632 509, Tamil Nadu, India.

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摘要：

A series of pyrano[4,3-b]pyran derivatives have been synthesized in excellent yields by the reaction of aromatic aldehydes with malononitrile or cyanoacetate and 4-hydroxy-6-methylpyran-2-one in water at 80℃, with the transformation being catalyzed by an aqueous solution of thiourea dioxide (TUD). Upon completion of the reaction, the product was isolated by filtration or extraction and the remaining aqueous TUD solution could be reused several times without any discernible impact on its catalytic activity. This procedure offers several advantages over existing procedures, including high yields, operational simplicity, the use of a non-toxic catalyst and solvent, short reaction time and minimum pollution of the environment, making it a useful and attractive process for the preparation of pyrano[4,3-b]pyran derivatives.

关键词: Pyrano[4,3-b]pyran, Thiourea dioxide, 4-Hydroxy-6-methylpyran-2-one, One-pot synthesis

Abstract:

A series of pyrano[4,3-b]pyran derivatives have been synthesized in excellent yields by the reaction of aromatic aldehydes with malononitrile or cyanoacetate and 4-hydroxy-6-methylpyran-2-one in water at 80℃, with the transformation being catalyzed by an aqueous solution of thiourea dioxide (TUD). Upon completion of the reaction, the product was isolated by filtration or extraction and the remaining aqueous TUD solution could be reused several times without any discernible impact on its catalytic activity. This procedure offers several advantages over existing procedures, including high yields, operational simplicity, the use of a non-toxic catalyst and solvent, short reaction time and minimum pollution of the environment, making it a useful and attractive process for the preparation of pyrano[4,3-b]pyran derivatives.

Key words: Pyrano[4,3-b]pyran, Thiourea dioxide, 4-Hydroxy-6-methylpyran-2-one, One-pot synthesis