Acetic acid-catalyzed selective synthesis of N-substituted 2-amino-3-cyanopyrroles via a three-component reaction between carbohydrates, primary amines and malononitrile
Direct conversion of unprotected carbohydrates to N-heterocycles is challenging and highly desirable. A simple three-component synthesis of N-substituted 2-amino-3-cyanopyrrole key framework is developed from the reaction between unprotected carbohydrates, malononitrile, and primary amines. The reac...
| Main Authors: | , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2022
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| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/163329 |
| _version_ | 1811676713934913536 |
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| author | Xia, Mengxin Moussa, Ziad Judeh, Zaher M. A. |
| author2 | School of Chemical and Biomedical Engineering |
| author_facet | School of Chemical and Biomedical Engineering Xia, Mengxin Moussa, Ziad Judeh, Zaher M. A. |
| author_sort | Xia, Mengxin |
| collection | NTU |
| description | Direct conversion of unprotected carbohydrates to N-heterocycles is challenging and highly desirable. A simple three-component synthesis of N-substituted 2-amino-3-cyanopyrrole key framework is developed from the reaction between unprotected carbohydrates, malononitrile, and primary amines. The reaction proceeded under mild reaction conditions (AcOH catalyst, EtOH, 60 °C, 2 hours), tolerated a wide substrate scope, worked smoothly on a 4 g scale, and gave the pyrroles in up to 86% yield. The pyrroles were also converted into functional intermediates to demonstrate their versatility. NMR and LC–MS experiments supported a proposed cascade reaction mechanism. The approach demonstrates a robust upcycling process for the challenging synthesis of highly functionalized N-heterocyclic compounds from unprotected carbohydrates. |
| first_indexed | 2024-10-01T02:25:51Z |
| format | Journal Article |
| id | ntu-10356/163329 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T02:25:51Z |
| publishDate | 2022 |
| record_format | dspace |
| spelling | ntu-10356/1633292022-12-02T06:07:54Z Acetic acid-catalyzed selective synthesis of N-substituted 2-amino-3-cyanopyrroles via a three-component reaction between carbohydrates, primary amines and malononitrile Xia, Mengxin Moussa, Ziad Judeh, Zaher M. A. School of Chemical and Biomedical Engineering Engineering::Chemical engineering Carbohydrates Cascade Reactions Direct conversion of unprotected carbohydrates to N-heterocycles is challenging and highly desirable. A simple three-component synthesis of N-substituted 2-amino-3-cyanopyrrole key framework is developed from the reaction between unprotected carbohydrates, malononitrile, and primary amines. The reaction proceeded under mild reaction conditions (AcOH catalyst, EtOH, 60 °C, 2 hours), tolerated a wide substrate scope, worked smoothly on a 4 g scale, and gave the pyrroles in up to 86% yield. The pyrroles were also converted into functional intermediates to demonstrate their versatility. NMR and LC–MS experiments supported a proposed cascade reaction mechanism. The approach demonstrates a robust upcycling process for the challenging synthesis of highly functionalized N-heterocyclic compounds from unprotected carbohydrates. Nanyang Technological University We thank Nanyang Technological University, Singapore, for the start-up grant. 2022-12-02T06:07:53Z 2022-12-02T06:07:53Z 2022 Journal Article Xia, M., Moussa, Z. & Judeh, Z. M. A. (2022). Acetic acid-catalyzed selective synthesis of N-substituted 2-amino-3-cyanopyrroles via a three-component reaction between carbohydrates, primary amines and malononitrile. Asian Journal of Organic Chemistry, 11(9), e202200367-. https://dx.doi.org/10.1002/ajoc.202200367 2193-5807 https://hdl.handle.net/10356/163329 10.1002/ajoc.202200367 2-s2.0-85136475145 9 11 e202200367 en NTU-SUG Asian Journal of Organic Chemistry © 2022 Wiley-VCH GmbH. All rights reserved. |
| spellingShingle | Engineering::Chemical engineering Carbohydrates Cascade Reactions Xia, Mengxin Moussa, Ziad Judeh, Zaher M. A. Acetic acid-catalyzed selective synthesis of N-substituted 2-amino-3-cyanopyrroles via a three-component reaction between carbohydrates, primary amines and malononitrile |
| title | Acetic acid-catalyzed selective synthesis of N-substituted 2-amino-3-cyanopyrroles via a three-component reaction between carbohydrates, primary amines and malononitrile |
| title_full | Acetic acid-catalyzed selective synthesis of N-substituted 2-amino-3-cyanopyrroles via a three-component reaction between carbohydrates, primary amines and malononitrile |
| title_fullStr | Acetic acid-catalyzed selective synthesis of N-substituted 2-amino-3-cyanopyrroles via a three-component reaction between carbohydrates, primary amines and malononitrile |
| title_full_unstemmed | Acetic acid-catalyzed selective synthesis of N-substituted 2-amino-3-cyanopyrroles via a three-component reaction between carbohydrates, primary amines and malononitrile |
| title_short | Acetic acid-catalyzed selective synthesis of N-substituted 2-amino-3-cyanopyrroles via a three-component reaction between carbohydrates, primary amines and malononitrile |
| title_sort | acetic acid catalyzed selective synthesis of n substituted 2 amino 3 cyanopyrroles via a three component reaction between carbohydrates primary amines and malononitrile |
| topic | Engineering::Chemical engineering Carbohydrates Cascade Reactions |
| url | https://hdl.handle.net/10356/163329 |
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