Synthesis of 2-Amino-4,6-diarylnicotinonitriles Using Silica-Bound N-Propyl Triethylenetetramine Sulfamic Acid as a Recyclable Solid Acid Catalyst

doi:10.1016/S1872-2067(11)60421-X

催化学报 ›› 2012, Vol. 33 ›› Issue (8): 1312-1317.DOI: 10.1016/S1872-2067(11)60421-X

Synthesis of 2-Amino-4,6-diarylnicotinonitriles Using Silica-Bound N-Propyl Triethylenetetramine Sulfamic Acid as a Recyclable Solid Acid Catalyst

Khodabakhsh NIKNAM*, Abbas JAMALI, Marzieh TAJADDOD, Abdollah DERIS

Department of Chemistry, Faculty of Sciences, Persian Gulf University, Bushehr 75169, Iran

收稿日期:2012-03-06 修回日期:2012-05-03 出版日期:2012-08-01 发布日期:2012-08-01

Synthesis of 2-Amino-4,6-diarylnicotinonitriles Using Silica-Bound N-Propyl Triethylenetetramine Sulfamic Acid as a Recyclable Solid Acid Catalyst

Khodabakhsh NIKNAM*, Abbas JAMALI, Marzieh TAJADDOD, Abdollah DERIS

Department of Chemistry, Faculty of Sciences, Persian Gulf University, Bushehr 75169, Iran

Received:2012-03-06 Revised:2012-05-03 Online:2012-08-01 Published:2012-08-01

摘要/Abstract

摘要： A simple and efficient procedure for the preparation of silica-bound N-propyl triethylenetetramine sulfamic acid (SBPTETSA) by the reaction of silica-bound N-propyl triethylenetetramine (SBPTET) with chlorosulfonic acid in chloroform is described. Silica-bound N-propyl triethylenetetramine sulfamic acid was employed as a recyclable catalyst for the synthesis of 2-amino-4,6-diarylnicotinonitriles from the multi-component reaction of an acetophenone derivative, an aromatic aldehyde, malononitrile, and ammonium acetate under solvent-free conditions at 100 °C. The heterogeneous catalyst was recycled for five consecutive runs in the optimized multi-component reaction of 4-chloroacetophenone, 4-chloroenzaldehyde, malononitrile, and ammonium acetate without significant loses to its catalytic activity.

关键词: silica-bonded N-propyl triethylenetetramine sulfamic acid, 2-amino-4,6-diarylnicotinonitrile, pyridine, aldehyde, solvent-free

Abstract: A simple and efficient procedure for the preparation of silica-bound N-propyl triethylenetetramine sulfamic acid (SBPTETSA) by the reaction of silica-bound N-propyl triethylenetetramine (SBPTET) with chlorosulfonic acid in chloroform is described. Silica-bound N-propyl triethylenetetramine sulfamic acid was employed as a recyclable catalyst for the synthesis of 2-amino-4,6-diarylnicotinonitriles from the multi-component reaction of an acetophenone derivative, an aromatic aldehyde, malononitrile, and ammonium acetate under solvent-free conditions at 100 °C. The heterogeneous catalyst was recycled for five consecutive runs in the optimized multi-component reaction of 4-chloroacetophenone, 4-chloroenzaldehyde, malononitrile, and ammonium acetate without significant loses to its catalytic activity.

Key words: silica-bonded N-propyl triethylenetetramine sulfamic acid, 2-amino-4,6-diarylnicotinonitrile, pyridine, aldehyde, solvent-free

Khodabakhsh NIKNAM, Abbas JAMALI, Marzieh TAJADDOD, Abdollah DERIS. Synthesis of 2-Amino-4,6-diarylnicotinonitriles Using Silica-Bound N-Propyl Triethylenetetramine Sulfamic Acid as a Recyclable Solid Acid Catalyst[J]. 催化学报, 2012, 33(8): 1312-1317.

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参考文献

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Synthesis of 2-Amino-4,6-diarylnicotinonitriles Using Silica-Bound N-Propyl Triethylenetetramine Sulfamic Acid as a Recyclable Solid Acid Catalyst

Synthesis of 2-Amino-4,6-diarylnicotinonitriles Using Silica-Bound N-Propyl Triethylenetetramine Sulfamic Acid as a Recyclable Solid Acid Catalyst

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