4,4’-trimethylenedipiperidine as a nitrogen heterocycle solvent and/or catalyst: Liquid phase tandem Knoevenagel–Michael condensation
Liquid phase tandem Knoevenagel-Michael condensation of various aromatic and heteroaromatic aldehydes with barbituric acid or 2-thiobarbituric acid and malononitrile was studied in a one-pot three-component reaction. For the first time, TMDP was employed as a safe and efficient solvent and/or cataly...
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my.um.eprints.258922021-04-28T01:40:18Z http://eprints.um.edu.my/25892/ 4,4’-trimethylenedipiperidine as a nitrogen heterocycle solvent and/or catalyst: Liquid phase tandem Knoevenagel–Michael condensation Zaharani, Lia Khaligh, Nader Ghaffari Gorjian, Hayede Johan, Mohd Rafie QC Physics QD Chemistry Liquid phase tandem Knoevenagel-Michael condensation of various aromatic and heteroaromatic aldehydes with barbituric acid or 2-thiobarbituric acid and malononitrile was studied in a one-pot three-component reaction. For the first time, TMDP was employed as a safe and efficient solvent and/or catalyst in the liquid and aqueous ethanol medium, respectively, for the practical and eco-friendly Knoevenagel-Michael condensation. The reactions were carried out by using greener procedures, including a) the use of TMDP as an N-heterocycle organocatalyst in a green medium including water and ethanol (1:1 v/v) at reflux temperature, and b) the use of TMDP as a dual solvent-catalyst at 65 °C in the absence of any solvent. High to excellent yields of the desired pyrano[2,3-d] pyrimidinones were obtained under the two earlier mentioned conditions. The current methodologies have advantages, including (a) avoiding hazardous, toxic, volatile, and flammable materials and solvents, (b) avoiding tedious processes, harsh conditions, and multiple steps for the preparation of catalysts, (c) using a less toxic and noncorrosive catalyst, (d) minimizing hazardous waste generation and simple workup process, and (e) high recyclability of TMDP. Another important result of this work is that the TMDP can be a promising alternative for toxic, volatile, and flammable base reagents such as piperidine and triethylamine in liquid phase organic syntheses owing to its unique properties such as being less toxic, nonflammable, and nonvolatile, and having a low melting point, broad liquid range temperature, high thermal stability, and safe handling and storage. © This work is licensed under a Creative Commons Attribution 4.0 International License. TUBITAK 2021 Article PeerReviewed Zaharani, Lia and Khaligh, Nader Ghaffari and Gorjian, Hayede and Johan, Mohd Rafie (2021) 4,4’-trimethylenedipiperidine as a nitrogen heterocycle solvent and/or catalyst: Liquid phase tandem Knoevenagel–Michael condensation. Turkish Journal of Chemistry, 45 (1). pp. 261-268. ISSN 1303-6130 https://doi.org/10.3906/KIM-2010-41 doi:10.3906/KIM-2010-41 |
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QC Physics QD Chemistry Zaharani, Lia Khaligh, Nader Ghaffari Gorjian, Hayede Johan, Mohd Rafie 4,4’-trimethylenedipiperidine as a nitrogen heterocycle solvent and/or catalyst: Liquid phase tandem Knoevenagel–Michael condensation |
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Liquid phase tandem Knoevenagel-Michael condensation of various aromatic and heteroaromatic aldehydes with barbituric acid or 2-thiobarbituric acid and malononitrile was studied in a one-pot three-component reaction. For the first time, TMDP was employed as a safe and efficient solvent and/or catalyst in the liquid and aqueous ethanol medium, respectively, for the practical and eco-friendly Knoevenagel-Michael condensation. The reactions were carried out by using greener procedures, including a) the use of TMDP as an N-heterocycle organocatalyst in a green medium including water and ethanol (1:1 v/v) at reflux temperature, and b) the use of TMDP as a dual solvent-catalyst at 65 °C in the absence of any solvent. High to excellent yields of the desired pyrano[2,3-d] pyrimidinones were obtained under the two earlier mentioned conditions. The current methodologies have advantages, including (a) avoiding hazardous, toxic, volatile, and flammable materials and solvents, (b) avoiding tedious processes, harsh conditions, and multiple steps for the preparation of catalysts, (c) using a less toxic and noncorrosive catalyst, (d) minimizing hazardous waste generation and simple workup process, and (e) high recyclability of TMDP. Another important result of this work is that the TMDP can be a promising alternative for toxic, volatile, and flammable base reagents such as piperidine and triethylamine in liquid phase organic syntheses owing to its unique properties such as being less toxic, nonflammable, and nonvolatile, and having a low melting point, broad liquid range temperature, high thermal stability, and safe handling and storage. © This work is licensed under a Creative Commons Attribution 4.0 International License. |
format |
Article |
author |
Zaharani, Lia Khaligh, Nader Ghaffari Gorjian, Hayede Johan, Mohd Rafie |
author_facet |
Zaharani, Lia Khaligh, Nader Ghaffari Gorjian, Hayede Johan, Mohd Rafie |
author_sort |
Zaharani, Lia |
title |
4,4’-trimethylenedipiperidine as a nitrogen heterocycle solvent and/or catalyst: Liquid phase tandem Knoevenagel–Michael condensation |
title_short |
4,4’-trimethylenedipiperidine as a nitrogen heterocycle solvent and/or catalyst: Liquid phase tandem Knoevenagel–Michael condensation |
title_full |
4,4’-trimethylenedipiperidine as a nitrogen heterocycle solvent and/or catalyst: Liquid phase tandem Knoevenagel–Michael condensation |
title_fullStr |
4,4’-trimethylenedipiperidine as a nitrogen heterocycle solvent and/or catalyst: Liquid phase tandem Knoevenagel–Michael condensation |
title_full_unstemmed |
4,4’-trimethylenedipiperidine as a nitrogen heterocycle solvent and/or catalyst: Liquid phase tandem Knoevenagel–Michael condensation |
title_sort |
4,4’-trimethylenedipiperidine as a nitrogen heterocycle solvent and/or catalyst: liquid phase tandem knoevenagel–michael condensation |
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TUBITAK |
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2021 |
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http://eprints.um.edu.my/25892/ https://doi.org/10.3906/KIM-2010-41 |
_version_ |
1698697320955117568 |
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