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Expanding the chemical space of 3(5)-functionalized 1,2,4-triazoles
- Source :
- Chemistry of Heterocyclic Compounds. 58:116-128
- Publication Year :
- 2022
- Publisher :
- Springer Science and Business Media LLC, 2022.
-
Abstract
- An efficient approach to the gram-scale synthesis of 3(5)-substituted, 1,3- and 1,5-disubstituted 1,2,4-triazole-derived building blocks is described. The key synthetic precursors - 1,2,4-triazole-3(5)-carboxylates (20 examples, 35-89% yield) were prepared from readily available acyl hydrazides and ethyl 2-ethoxy-2-iminoacetate hydrochloride. Further transformations were performed following the convergent synthetic strategy and allowed the preparation of 1,3- and 1,5-disubstituted 1,2,4-triazole-derived esters (16 examples, 25-75% yield), 3(5)-substituted, 1,3- and 1,5-disubstituted carboxylate salts (18 examples, 78-93% yield), amides (5 examples, 82-93% yield), nitriles (5 examples, 30-85% yield), hydrazides (6 examples, 84-89% yield), and hydroxamic acids (3 examples, 73-78% yield). Considering wide applications of the 1,2,4-triazole motif in medicinal chemistry, these compounds are valuable building blocks for lead-oriented synthesis; they have also great potential for coordination chemistry.The online version contains supplementary material available at 10.1007/s10593-022-03064-z.
- Subjects :
- Organic Chemistry
Subjects
Details
- ISSN :
- 15738353 and 00093122
- Volume :
- 58
- Database :
- OpenAIRE
- Journal :
- Chemistry of Heterocyclic Compounds
- Accession number :
- edsair.doi.dedup.....f267d9cadc29591cefb9753752fe12df