Cu(II)-Catalysed Hydrocarboxylation of Imines Utilizing CO<sub>2</sub> to Synthesize α-Unsaturated Aminocarboxylic Acids
Here, we report the Cu(II)-photocatalysed hydrocarboxylation of imines (C=N) from a series of synthesized Schiff Base derivatives, namely <i>(E)-1-(4-((4-methylbenzylidene)amino)phenyl)ethanone</i>, (<i>E</i>)-1-(3-((5-bromo-2-hydroxybenzylidene)amino)phenyl)ethanone, (E)-4-(...
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-10-01
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| Series: | Pharmaceuticals |
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| Online Access: | https://www.mdpi.com/1424-8247/15/10/1240 |
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| author | Allen T. Gordon Eric C. Hosten Adeniyi S. Ogunlaja |
| author_facet | Allen T. Gordon Eric C. Hosten Adeniyi S. Ogunlaja |
| author_sort | Allen T. Gordon |
| collection | DOAJ |
| description | Here, we report the Cu(II)-photocatalysed hydrocarboxylation of imines (C=N) from a series of synthesized Schiff Base derivatives, namely <i>(E)-1-(4-((4-methylbenzylidene)amino)phenyl)ethanone</i>, (<i>E</i>)-1-(3-((5-bromo-2-hydroxybenzylidene)amino)phenyl)ethanone, (E)-4-((5-bromo-2-hydroxybenzylidene)amino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one, and (E)-1,5-dimethyl-4-((4-methylbenzylidene)amino)-2-phenyl-1H-pyrazol-3(2H)-one, with carbon dioxide (CO<sub>2</sub>) to generate disubstituted amino acids. Under mild conditions (atmospheric pressure of CO<sub>2</sub>, room temperature, and 30 W Blue LED light), good to excellent yields confirming the formation of substituted amino acid unsaturated acid derivatives were obtained. Single crystal X-ray diffraction (SC-XRD) and UV-Vis diffuse reflectance spectroscopy (UV-Vis-DRS) confirmed the square pyramidal geometry of the Cu(II) photocatalyst. Docking and DFT calculations of the substituted amino acid unsaturated acid derivatives showed their potential as antimicrobial molecules. |
| first_indexed | 2024-03-09T19:36:58Z |
| format | Article |
| id | doaj.art-db0ebf314003437bbec2b4b0a3a519a5 |
| institution | Directory Open Access Journal |
| issn | 1424-8247 |
| language | English |
| last_indexed | 2024-03-09T19:36:58Z |
| publishDate | 2022-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Pharmaceuticals |
| spelling | doaj.art-db0ebf314003437bbec2b4b0a3a519a52023-11-24T01:51:41ZengMDPI AGPharmaceuticals1424-82472022-10-011510124010.3390/ph15101240Cu(II)-Catalysed Hydrocarboxylation of Imines Utilizing CO<sub>2</sub> to Synthesize α-Unsaturated Aminocarboxylic AcidsAllen T. Gordon0Eric C. Hosten1Adeniyi S. Ogunlaja2Department of Chemistry, Nelson Mandela University, Gqeberha P.O. Box 77000, South AfricaDepartment of Chemistry, Nelson Mandela University, Gqeberha P.O. Box 77000, South AfricaDepartment of Chemistry, Nelson Mandela University, Gqeberha P.O. Box 77000, South AfricaHere, we report the Cu(II)-photocatalysed hydrocarboxylation of imines (C=N) from a series of synthesized Schiff Base derivatives, namely <i>(E)-1-(4-((4-methylbenzylidene)amino)phenyl)ethanone</i>, (<i>E</i>)-1-(3-((5-bromo-2-hydroxybenzylidene)amino)phenyl)ethanone, (E)-4-((5-bromo-2-hydroxybenzylidene)amino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one, and (E)-1,5-dimethyl-4-((4-methylbenzylidene)amino)-2-phenyl-1H-pyrazol-3(2H)-one, with carbon dioxide (CO<sub>2</sub>) to generate disubstituted amino acids. Under mild conditions (atmospheric pressure of CO<sub>2</sub>, room temperature, and 30 W Blue LED light), good to excellent yields confirming the formation of substituted amino acid unsaturated acid derivatives were obtained. Single crystal X-ray diffraction (SC-XRD) and UV-Vis diffuse reflectance spectroscopy (UV-Vis-DRS) confirmed the square pyramidal geometry of the Cu(II) photocatalyst. Docking and DFT calculations of the substituted amino acid unsaturated acid derivatives showed their potential as antimicrobial molecules.https://www.mdpi.com/1424-8247/15/10/1240Schiff basesCO<sub>2</sub>α-unsaturated carboxylic acidshydrocarboxylationCu(II) catalysts |
| spellingShingle | Allen T. Gordon Eric C. Hosten Adeniyi S. Ogunlaja Cu(II)-Catalysed Hydrocarboxylation of Imines Utilizing CO<sub>2</sub> to Synthesize α-Unsaturated Aminocarboxylic Acids Pharmaceuticals Schiff bases CO<sub>2</sub> α-unsaturated carboxylic acids hydrocarboxylation Cu(II) catalysts |
| title | Cu(II)-Catalysed Hydrocarboxylation of Imines Utilizing CO<sub>2</sub> to Synthesize α-Unsaturated Aminocarboxylic Acids |
| title_full | Cu(II)-Catalysed Hydrocarboxylation of Imines Utilizing CO<sub>2</sub> to Synthesize α-Unsaturated Aminocarboxylic Acids |
| title_fullStr | Cu(II)-Catalysed Hydrocarboxylation of Imines Utilizing CO<sub>2</sub> to Synthesize α-Unsaturated Aminocarboxylic Acids |
| title_full_unstemmed | Cu(II)-Catalysed Hydrocarboxylation of Imines Utilizing CO<sub>2</sub> to Synthesize α-Unsaturated Aminocarboxylic Acids |
| title_short | Cu(II)-Catalysed Hydrocarboxylation of Imines Utilizing CO<sub>2</sub> to Synthesize α-Unsaturated Aminocarboxylic Acids |
| title_sort | cu ii catalysed hydrocarboxylation of imines utilizing co sub 2 sub to synthesize α unsaturated aminocarboxylic acids |
| topic | Schiff bases CO<sub>2</sub> α-unsaturated carboxylic acids hydrocarboxylation Cu(II) catalysts |
| url | https://www.mdpi.com/1424-8247/15/10/1240 |
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