Selective One-Pot Multicomponent Synthesis of <i>N</i>-Substituted 2,3,5-Functionalized 3-Cyanopyrroles via the Reaction between α-Hydroxyketones, Oxoacetonitriles, and Primary Amines
A one-step, three-component reaction between α-hydroxyketones, oxoacetonitriles, and primary amines gives <i>N</i>-substituted 2,3,5-functionalized 3-cyanopyrroles with complete selectivity in up to 90% isolated yields. The reaction worked on a wide substrate scope under mild reaction co...
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-08-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/16/5285 |
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| author | Mengxin Xia Ziad Moussa Zaher M. A. Judeh |
| author_facet | Mengxin Xia Ziad Moussa Zaher M. A. Judeh |
| author_sort | Mengxin Xia |
| collection | DOAJ |
| description | A one-step, three-component reaction between α-hydroxyketones, oxoacetonitriles, and primary amines gives <i>N</i>-substituted 2,3,5-functionalized 3-cyanopyrroles with complete selectivity in up to 90% isolated yields. The reaction worked on a wide substrate scope under mild reaction conditions (AcOH as a catalyst, EtOH, 70 °C, 3 h). The reaction proceeded with very high atom efficiency as water is the only molecule lost during the reaction. The practicality of the reaction was demonstrated on a large gram scale. The structures of the 3-cyanopyrroles were confirmed by single-crystal X-ray diffraction and NMR; this work provides a general and practical entry to pyrrole scaffolds suitably decorated for the synthesis of various bioactive pyrroles in a concise manner. |
| first_indexed | 2024-03-09T04:03:03Z |
| format | Article |
| id | doaj.art-eec859bab45c42c796dafe6e12e78a75 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T04:03:03Z |
| publishDate | 2022-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-eec859bab45c42c796dafe6e12e78a752023-12-03T14:12:02ZengMDPI AGMolecules1420-30492022-08-012716528510.3390/molecules27165285Selective One-Pot Multicomponent Synthesis of <i>N</i>-Substituted 2,3,5-Functionalized 3-Cyanopyrroles via the Reaction between α-Hydroxyketones, Oxoacetonitriles, and Primary AminesMengxin Xia0Ziad Moussa1Zaher M. A. Judeh2School of Chemical and Biomedical Engineering, Nanyang Technological University, 62 Nanyang Drive, N1.2–B1-14, Singapore 637459, SingaporeDepartment of Chemistry, College of Science, United Arab Emirates University, Al Ain P.O. Box 15551, United Arab EmiratesSchool of Chemical and Biomedical Engineering, Nanyang Technological University, 62 Nanyang Drive, N1.2–B1-14, Singapore 637459, SingaporeA one-step, three-component reaction between α-hydroxyketones, oxoacetonitriles, and primary amines gives <i>N</i>-substituted 2,3,5-functionalized 3-cyanopyrroles with complete selectivity in up to 90% isolated yields. The reaction worked on a wide substrate scope under mild reaction conditions (AcOH as a catalyst, EtOH, 70 °C, 3 h). The reaction proceeded with very high atom efficiency as water is the only molecule lost during the reaction. The practicality of the reaction was demonstrated on a large gram scale. The structures of the 3-cyanopyrroles were confirmed by single-crystal X-ray diffraction and NMR; this work provides a general and practical entry to pyrrole scaffolds suitably decorated for the synthesis of various bioactive pyrroles in a concise manner.https://www.mdpi.com/1420-3049/27/16/5285pyrrolescarbohydratessustainable synthesisthree-component reactionsone-pot reactions |
| spellingShingle | Mengxin Xia Ziad Moussa Zaher M. A. Judeh Selective One-Pot Multicomponent Synthesis of <i>N</i>-Substituted 2,3,5-Functionalized 3-Cyanopyrroles via the Reaction between α-Hydroxyketones, Oxoacetonitriles, and Primary Amines Molecules pyrroles carbohydrates sustainable synthesis three-component reactions one-pot reactions |
| title | Selective One-Pot Multicomponent Synthesis of <i>N</i>-Substituted 2,3,5-Functionalized 3-Cyanopyrroles via the Reaction between α-Hydroxyketones, Oxoacetonitriles, and Primary Amines |
| title_full | Selective One-Pot Multicomponent Synthesis of <i>N</i>-Substituted 2,3,5-Functionalized 3-Cyanopyrroles via the Reaction between α-Hydroxyketones, Oxoacetonitriles, and Primary Amines |
| title_fullStr | Selective One-Pot Multicomponent Synthesis of <i>N</i>-Substituted 2,3,5-Functionalized 3-Cyanopyrroles via the Reaction between α-Hydroxyketones, Oxoacetonitriles, and Primary Amines |
| title_full_unstemmed | Selective One-Pot Multicomponent Synthesis of <i>N</i>-Substituted 2,3,5-Functionalized 3-Cyanopyrroles via the Reaction between α-Hydroxyketones, Oxoacetonitriles, and Primary Amines |
| title_short | Selective One-Pot Multicomponent Synthesis of <i>N</i>-Substituted 2,3,5-Functionalized 3-Cyanopyrroles via the Reaction between α-Hydroxyketones, Oxoacetonitriles, and Primary Amines |
| title_sort | selective one pot multicomponent synthesis of i n i substituted 2 3 5 functionalized 3 cyanopyrroles via the reaction between α hydroxyketones oxoacetonitriles and primary amines |
| topic | pyrroles carbohydrates sustainable synthesis three-component reactions one-pot reactions |
| url | https://www.mdpi.com/1420-3049/27/16/5285 |
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