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 hyd...
| Main Authors: | , , , |
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| Format: | Journal Article |
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Royal Society of Chemistry
2018
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| Online Access: | http://hdl.handle.net/20.500.11937/69766 |
| _version_ | 1848762129152212992 |
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| author | Lim, F. Tan, L. Tiekink, E. Dolzhenko, Anton |
| author_facet | Lim, F. Tan, L. Tiekink, E. Dolzhenko, Anton |
| author_sort | Lim, F. |
| building | Curtin 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.
Graphical abstract: Synthesis of 3-(5-amino-1H-1,2,4-triazol-3-yl)propanamides and their tautomerism |
| first_indexed | 2025-11-14T10:42:39Z |
| format | Journal Article |
| id | curtin-20.500.11937-69766 |
| institution | Curtin University Malaysia |
| institution_category | Local University |
| last_indexed | 2025-11-14T10:42:39Z |
| publishDate | 2018 |
| publisher | Royal Society of Chemistry |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | curtin-20.500.11937-697662019-01-29T05:34:53Z Synthesis of 3-(5-amino-1H-1,2,4-triazol-3-yl)propanamides and their tautomerism Lim, F. Tan, L. Tiekink, E. Dolzhenko, Anton 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. Graphical abstract: Synthesis of 3-(5-amino-1H-1,2,4-triazol-3-yl)propanamides and their tautomerism 2018 Journal Article http://hdl.handle.net/20.500.11937/69766 10.1039/c8ra04576c http://creativecommons.org/licenses/by/3.0/ Royal Society of Chemistry fulltext |
| spellingShingle | Lim, F. Tan, L. Tiekink, E. Dolzhenko, Anton 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 |
| url | http://hdl.handle.net/20.500.11937/69766 |