催化学报

催化学报 ›› 2014, Vol. 35 ›› Issue (10): 1761-1767.DOI: 10.1016/S1872-2067(14)60174-1

• 论文 • 上一篇    下一篇

Application of a Keplerate type giant nanoporous isopolyoxomolybdate as a reusable catalyst for the synthesis of 1,2,4,5-tetrasubstituted imidazoles

Ahmad Nakhaei, Abolghasem Davoodnia   

  1. Department of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad, Iran
  • 收稿日期:2014-04-21 修回日期:2014-06-09 出版日期:2014-09-28 发布日期:2014-09-30
  • 通讯作者: Abolghasem Davoodnia

Application of a Keplerate type giant nanoporous isopolyoxomolybdate as a reusable catalyst for the synthesis of 1,2,4,5-tetrasubstituted imidazoles

Ahmad Nakhaei, Abolghasem Davoodnia   

  1. Department of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad, Iran
  • Received:2014-04-21 Revised:2014-06-09 Online:2014-09-28 Published:2014-09-30

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摘要：

The Keplerate-type giant nanoporous isopolyoxomolybdate (NH4)42[MoVI72MoV60O372- (CH3COO)30(H2O)72], denoted {Mo132}, has been used as a catalyst for the synthesis of 1,2,4,5-tetrasubstituted imidazoles by the one-pot, four-component thermal reaction of benzil with aromatic aldehydes, primary amines, and ammonium acetate under solvent-free conditions. The catalyst was prepared according to a previously published literature procedure using inexpensive and readily available starting materials, and subsequently characterized by FT-IR, UV and X-ray diffraction spectroscopy, as well as microanalysis. The results showed that {Mo132} exhibited high catalytic activity towards the synthesis of 1,2,4,5-tetrasubstituted imidazoles, with the desired products being formed in good to high yields. Furthermore, the catalyst was recyclable and could be reused at least three times without any discernible loss in its catalytic activity. Overall, this new catalytic method for the synthesis of 1,2,4,5-tetrasubstituted imidazoles provides rapid access to the desired compounds following a simple work-up procedure, and avoids the use of harmful organic solvents. This method therefore represents a significant improvement over the methods currently available for the synthesis of tetrasubstituted imidazoles.

关键词: Giant Nanoporous, isopolyoxomolybdate, Keplerate, Solvent-free condition, 1,2,4,5-tetrasubstituted imidazole

Abstract:

The Keplerate-type giant nanoporous isopolyoxomolybdate (NH4)42[MoVI72MoV60O372- (CH3COO)30(H2O)72], denoted {Mo132}, has been used as a catalyst for the synthesis of 1,2,4,5-tetrasubstituted imidazoles by the one-pot, four-component thermal reaction of benzil with aromatic aldehydes, primary amines, and ammonium acetate under solvent-free conditions. The catalyst was prepared according to a previously published literature procedure using inexpensive and readily available starting materials, and subsequently characterized by FT-IR, UV and X-ray diffraction spectroscopy, as well as microanalysis. The results showed that {Mo132} exhibited high catalytic activity towards the synthesis of 1,2,4,5-tetrasubstituted imidazoles, with the desired products being formed in good to high yields. Furthermore, the catalyst was recyclable and could be reused at least three times without any discernible loss in its catalytic activity. Overall, this new catalytic method for the synthesis of 1,2,4,5-tetrasubstituted imidazoles provides rapid access to the desired compounds following a simple work-up procedure, and avoids the use of harmful organic solvents. This method therefore represents a significant improvement over the methods currently available for the synthesis of tetrasubstituted imidazoles.

Key words: Giant Nanoporous, isopolyoxomolybdate, Keplerate, Solvent-free condition, 1,2,4,5-tetrasubstituted imidazole