Synthesis and Ring-Chain Tautomerism of 1-(4-Ethoxyphenyl)-5-formyl-1<i>H</i>-1,2,3-triazole-4-carboxylic Acid: The First Representative of a 5-Formyl-1<i>H</i>-1,2,3-triazole-4-carboxylic Acids Series
Synthesis of the first representative of a 5-formyl-1<i>H</i>-1,2,3-triazole-4-carboxylic acids series – 1-(4-ethoxyphenyl)-5-formyl-1<i>H</i>-1,2,3-triazole-4-carboxylic acid was performed. The 1-azido-4-ethoxybenzene was chosen as a starting reagent in a two-step synthesis,...
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MDPI AG
2022-06-01
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| Online Access: | https://www.mdpi.com/1422-8599/2022/3/M1397 |
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| author | Nazariy T. Pokhodylo Mykola D. Obushak |
| author_facet | Nazariy T. Pokhodylo Mykola D. Obushak |
| author_sort | Nazariy T. Pokhodylo |
| collection | DOAJ |
| description | Synthesis of the first representative of a 5-formyl-1<i>H</i>-1,2,3-triazole-4-carboxylic acids series – 1-(4-ethoxyphenyl)-5-formyl-1<i>H</i>-1,2,3-triazole-4-carboxylic acid was performed. The 1-azido-4-ethoxybenzene was chosen as a starting reagent in a two-step synthesis, which reacted with the ethyl 4,4-diethoxy-3-oxobutanoate under base catalysis to form ethyl 5-(diethoxymethyl)-1-(4-ethoxyphenyl)-1H-1,2,3-triazole-4-carboxylate with protected formyl and acid groups. By the subsequent saponification of the ester group and removing of acetal protection, the target 1-(4-ethoxyphenyl)-5-formyl-1H-1,2,3-triazole-4-carboxylic acid was obtained. It has been found that the free acid form predominated in the solution under its cyclic 6-hydroxy-1,6-dihydro-4<i>H</i>-furo[3,4-<i>d</i>][1,2,3]triazol-4-one tautomer. According to <sup>1</sup>H NMR, cyclic hemiacetal is about 20%. |
| first_indexed | 2024-03-09T23:04:08Z |
| format | Article |
| id | doaj.art-853d6c971acd411883f09a6dfcf51adb |
| institution | Directory Open Access Journal |
| issn | 1422-8599 |
| language | English |
| last_indexed | 2024-03-09T23:04:08Z |
| publishDate | 2022-06-01 |
| publisher | MDPI AG |
| record_format | Article |
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| spelling | doaj.art-853d6c971acd411883f09a6dfcf51adb2023-11-23T17:57:12ZengMDPI AGMolbank1422-85992022-06-0120223M139710.3390/M1397Synthesis and Ring-Chain Tautomerism of 1-(4-Ethoxyphenyl)-5-formyl-1<i>H</i>-1,2,3-triazole-4-carboxylic Acid: The First Representative of a 5-Formyl-1<i>H</i>-1,2,3-triazole-4-carboxylic Acids SeriesNazariy T. Pokhodylo0Mykola D. Obushak1Department of Organic Chemistry, Ivan Franko National University of Lviv, Kyryla i Mefodiya, 6, 79005 Lviv, UkraineDepartment of Organic Chemistry, Ivan Franko National University of Lviv, Kyryla i Mefodiya, 6, 79005 Lviv, UkraineSynthesis of the first representative of a 5-formyl-1<i>H</i>-1,2,3-triazole-4-carboxylic acids series – 1-(4-ethoxyphenyl)-5-formyl-1<i>H</i>-1,2,3-triazole-4-carboxylic acid was performed. The 1-azido-4-ethoxybenzene was chosen as a starting reagent in a two-step synthesis, which reacted with the ethyl 4,4-diethoxy-3-oxobutanoate under base catalysis to form ethyl 5-(diethoxymethyl)-1-(4-ethoxyphenyl)-1H-1,2,3-triazole-4-carboxylate with protected formyl and acid groups. By the subsequent saponification of the ester group and removing of acetal protection, the target 1-(4-ethoxyphenyl)-5-formyl-1H-1,2,3-triazole-4-carboxylic acid was obtained. It has been found that the free acid form predominated in the solution under its cyclic 6-hydroxy-1,6-dihydro-4<i>H</i>-furo[3,4-<i>d</i>][1,2,3]triazol-4-one tautomer. According to <sup>1</sup>H NMR, cyclic hemiacetal is about 20%.https://www.mdpi.com/1422-8599/2022/3/M13975-formyl-1<i>H</i>-1,2,3-triazole-4-carboxylic acidfuro[3,4-<i>d</i>][1,2,3]triazolearyl azides1,2,3-triazolesortho-formyl (het)aromatic carboxylic acidring-chain tautomerism |
| spellingShingle | Nazariy T. Pokhodylo Mykola D. Obushak Synthesis and Ring-Chain Tautomerism of 1-(4-Ethoxyphenyl)-5-formyl-1<i>H</i>-1,2,3-triazole-4-carboxylic Acid: The First Representative of a 5-Formyl-1<i>H</i>-1,2,3-triazole-4-carboxylic Acids Series Molbank 5-formyl-1<i>H</i>-1,2,3-triazole-4-carboxylic acid furo[3,4-<i>d</i>][1,2,3]triazole aryl azides 1,2,3-triazoles ortho-formyl (het)aromatic carboxylic acid ring-chain tautomerism |
| title | Synthesis and Ring-Chain Tautomerism of 1-(4-Ethoxyphenyl)-5-formyl-1<i>H</i>-1,2,3-triazole-4-carboxylic Acid: The First Representative of a 5-Formyl-1<i>H</i>-1,2,3-triazole-4-carboxylic Acids Series |
| title_full | Synthesis and Ring-Chain Tautomerism of 1-(4-Ethoxyphenyl)-5-formyl-1<i>H</i>-1,2,3-triazole-4-carboxylic Acid: The First Representative of a 5-Formyl-1<i>H</i>-1,2,3-triazole-4-carboxylic Acids Series |
| title_fullStr | Synthesis and Ring-Chain Tautomerism of 1-(4-Ethoxyphenyl)-5-formyl-1<i>H</i>-1,2,3-triazole-4-carboxylic Acid: The First Representative of a 5-Formyl-1<i>H</i>-1,2,3-triazole-4-carboxylic Acids Series |
| title_full_unstemmed | Synthesis and Ring-Chain Tautomerism of 1-(4-Ethoxyphenyl)-5-formyl-1<i>H</i>-1,2,3-triazole-4-carboxylic Acid: The First Representative of a 5-Formyl-1<i>H</i>-1,2,3-triazole-4-carboxylic Acids Series |
| title_short | Synthesis and Ring-Chain Tautomerism of 1-(4-Ethoxyphenyl)-5-formyl-1<i>H</i>-1,2,3-triazole-4-carboxylic Acid: The First Representative of a 5-Formyl-1<i>H</i>-1,2,3-triazole-4-carboxylic Acids Series |
| title_sort | synthesis and ring chain tautomerism of 1 4 ethoxyphenyl 5 formyl 1 i h i 1 2 3 triazole 4 carboxylic acid the first representative of a 5 formyl 1 i h i 1 2 3 triazole 4 carboxylic acids series |
| topic | 5-formyl-1<i>H</i>-1,2,3-triazole-4-carboxylic acid furo[3,4-<i>d</i>][1,2,3]triazole aryl azides 1,2,3-triazoles ortho-formyl (het)aromatic carboxylic acid ring-chain tautomerism |
| url | https://www.mdpi.com/1422-8599/2022/3/M1397 |
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