1,2,3-Triazole-4(5)-amines – Convenient Synthetic Blocks for the Construction of Triazolo-Annulated Heterocycles

Authors

DOI:

https://doi.org/10.24959/ophcj.22.258512

Keywords:

4(5)-amino-1,2,3-triazoles, triazolo[4,5-b]pyridines, triazolo[4,5-d]pyridines, triazoloannelated azepines, cyclocondensation

Abstract

Aim. To analyze and summarize the synthetic potential of 1,2,3-triazole-4(5)-amines as efficient building blocks in the synthesis of triazolo-annulated pyridine, azine and azepine systems.
Results and discussion. Original literature sources revealing the synthetic potential of 4(5)-amino functionalized 1,2,3-triazoles as convenient and available building blocks for the preparation of triazolo-annulated pyridines, azines and azepines were analyzed and systematized. Condensation of 1,2,3-triazole-4(5)-amines with methylene active compounds was shown to be a powerful tool for the synthesis of versatile triazolo[4,5-b]pyridines. In turn, the cyclocondensation based on 5-amino-1,2,3-triazole-4-carboxylic acids and their structurally modified derivatives was proven to be a general way for obtaining a number of triazolo[4,5-d]pyrimidine systems. Few representatives of triazolo-annulated pyridazines, 1,3-oxazines and 1,3-thiazines were synthesized by the intramolecular cyclization of the corresponding 4-aryl(carboxy-, aminomethyl)-5-amino-1,2,3-triazoles. The cyclocondensation involving 4,5-diamino-, 4-carbofunctionalized 5-amino-1,2,3-triazoles and 4-amino-5-thiocarboxamido-1,2,3-triazoles was successful for the construction of di-, oxa- and thiazepino-annulated triazoles.
Conclusions. The analysis, systematization and summary of the literature regarding the synthetic potential of 1,2,3-triazole-4(5)-amines conclusively demonstrate that these structures are easily available and convenient molecular blocks for the construction of triazolo-annulated pyridine, azine and azepine systems that are important for synthetic and biomedical research.

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2022-07-20

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Syrota, N. O.; Kemskiy, S. V.; Saliyeva, L. M.; Vovk, M. V. 1,2,3-Triazole-4(5)-Amines – Convenient Synthetic Blocks for the Construction of Triazolo-Annulated Heterocycles. J. Org. Pharm. Chem. 2022, 20, 27-51.

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Review Articles