Synthesis of 3-(5-amino-1H-1,2,4-triazol-3-yl) propanamides and their tautomerism
Two complementary pathways for the preparation of N-substituted 3-(5-amino-1H-1,2,4-triazol-3-yl) propanamides (5) were proposed and successfully realized in the synthesis of 20 representative examples. These methods use the same types of starting materials viz. succinic anhydride, aminoguanidine...
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| Language: | English |
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Royal Society of Chemistry
2018
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| Online Access: | http://eprints.sunway.edu.my/846/ http://eprints.sunway.edu.my/846/1/Tiekink%20Synthesis%20of%203-5.pdf |
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| author | Lim, Felicia Phei Lin Tan, Lin Yuing Tiekink, Edward R. T. * Dolzhenko, Anton V |
| author_facet | Lim, Felicia Phei Lin Tan, Lin Yuing Tiekink, Edward R. T. * Dolzhenko, Anton V |
| author_sort | Lim, Felicia Phei Lin |
| building | SU Institutional Repository |
| collection | Online Access |
| description | Two complementary pathways for the preparation of N-substituted 3-(5-amino-1H-1,2,4-triazol-3-yl)
propanamides (5) were proposed and successfully realized in the synthesis of 20 representative examples.
These methods use the same types of starting materials viz. succinic anhydride, aminoguanidine hydrochloride, and a variety of amines. The choice of the pathway and sequence of the introduction of reagents to the reaction depended on the amine nucleophilicity. The first pathway started with the preparation of N-guanidinosuccinimide, which then reacted with amines under microwave irradiation to
afford 5. The desired products were successfully obtained in the reaction with aliphatic amines (primary and
secondary) via a nucleophilic opening of the succinimide ring and the subsequent recyclization of the 1,2,4-
triazole ring. This approach however failed when less nucleophilic aromatic amines were used. Therefore, an
alternative pathway, with the initial preparation of N-arylsuccinimides and their subsequent reaction with
aminoguanidine hydrochloride under microwave irradiation, was applied. The annular prototropic tautomerism in the prepared 1,2,4-triazoles 5 was studied using NMR spectroscopy and X-ray crystallography. |
| first_indexed | 2025-11-14T21:14:57Z |
| format | Article |
| id | sunway-846 |
| institution | Sunway University |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T21:14:57Z |
| publishDate | 2018 |
| publisher | Royal Society of Chemistry |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | sunway-8462020-10-07T09:02:02Z http://eprints.sunway.edu.my/846/ Synthesis of 3-(5-amino-1H-1,2,4-triazol-3-yl) propanamides and their tautomerism Lim, Felicia Phei Lin Tan, Lin Yuing Tiekink, Edward R. T. * Dolzhenko, Anton V QD Chemistry Two complementary pathways for the preparation of N-substituted 3-(5-amino-1H-1,2,4-triazol-3-yl) propanamides (5) were proposed and successfully realized in the synthesis of 20 representative examples. These methods use the same types of starting materials viz. succinic anhydride, aminoguanidine hydrochloride, and a variety of amines. The choice of the pathway and sequence of the introduction of reagents to the reaction depended on the amine nucleophilicity. The first pathway started with the preparation of N-guanidinosuccinimide, which then reacted with amines under microwave irradiation to afford 5. The desired products were successfully obtained in the reaction with aliphatic amines (primary and secondary) via a nucleophilic opening of the succinimide ring and the subsequent recyclization of the 1,2,4- triazole ring. This approach however failed when less nucleophilic aromatic amines were used. Therefore, an alternative pathway, with the initial preparation of N-arylsuccinimides and their subsequent reaction with aminoguanidine hydrochloride under microwave irradiation, was applied. The annular prototropic tautomerism in the prepared 1,2,4-triazoles 5 was studied using NMR spectroscopy and X-ray crystallography. Royal Society of Chemistry 2018-06-12 Article PeerReviewed text en http://eprints.sunway.edu.my/846/1/Tiekink%20Synthesis%20of%203-5.pdf Lim, Felicia Phei Lin and Tan, Lin Yuing and Tiekink, Edward R. T. * and Dolzhenko, Anton V (2018) Synthesis of 3-(5-amino-1H-1,2,4-triazol-3-yl) propanamides and their tautomerism. RSC Advances, 8 (40). pp. 22351-22360. ISSN 2046-2069 http://www.rsc.li/rsc-advances DOI: 10.1039/c8ra04576c |
| spellingShingle | QD Chemistry Lim, Felicia Phei Lin Tan, Lin Yuing Tiekink, Edward R. T. * Dolzhenko, Anton V Synthesis of 3-(5-amino-1H-1,2,4-triazol-3-yl) propanamides and their tautomerism |
| title | Synthesis of 3-(5-amino-1H-1,2,4-triazol-3-yl)
propanamides and their tautomerism |
| title_full | Synthesis of 3-(5-amino-1H-1,2,4-triazol-3-yl)
propanamides and their tautomerism |
| title_fullStr | Synthesis of 3-(5-amino-1H-1,2,4-triazol-3-yl)
propanamides and their tautomerism |
| title_full_unstemmed | Synthesis of 3-(5-amino-1H-1,2,4-triazol-3-yl)
propanamides and their tautomerism |
| title_short | Synthesis of 3-(5-amino-1H-1,2,4-triazol-3-yl)
propanamides and their tautomerism |
| title_sort | synthesis of 3-(5-amino-1h-1,2,4-triazol-3-yl)
propanamides and their tautomerism |
| topic | QD Chemistry |
| url | http://eprints.sunway.edu.my/846/ http://eprints.sunway.edu.my/846/ http://eprints.sunway.edu.my/846/ http://eprints.sunway.edu.my/846/1/Tiekink%20Synthesis%20of%203-5.pdf |