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Synthesis and Ring-Chain Tautomerism of 1-(4-Ethoxyphenyl)-5-formyl-1H-1,2,3-triazole-4-carboxylic Acid: The First Representative of a 5-Formyl-1H-1,2,3-triazole-4-carboxylic Acids Series
| Content Provider | MDPI |
|---|---|
| Author | Pokhodylo, Nazariy T. Obushak, Mykola D. |
| Copyright Year | 2022 |
| Description | Synthesis of the first representative of a 5-formyl-1H-1,2,3-triazole-4-carboxylic acids series – 1-(4-ethoxyphenyl)-5-formyl-1H-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-4H-furo[3,4-d][1,2,3]triazol-4-one tautomer. According to$ ^{1}$H NMR, cyclic hemiacetal is about 20%. |
| Starting Page | M1397 |
| e-ISSN | 14228599 |
| DOI | 10.3390/M1397 |
| Journal | Molbank |
| Issue Number | 3 |
| Volume Number | 2022 |
| Language | English |
| Publisher | MDPI |
| Publisher Date | 2022-06-28 |
| Access Restriction | Open |
| Subject Keyword | Molbank 5-formyl-1h-1,2,3-triazole-4-carboxylic Acid Furo[3,4-d][1,2,3]triazole Aryl Azides 1,2,3-triazoles Ortho-formyl (het)aromatic Carboxylic Acid Ring-chain Tautomerism |
| Content Type | Text |
| Resource Type | Article |
