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.

Supporting Agency

  • The work is a part of the departmental research at the Institute of Organic Chemistry on the topic “Functional design, synthesis and directed modification of bioattractive condensed azole, azine and azepine compounds” (the State Registration No. 0120U104977; the research period: 2021 – 2025). The work was supported by the National Academy of Sciences of Ukraine (grant No. 19/02 – 2021(3)) to groups of young scientists of the National Academy of Sciences of Ukraine (2021-2022)

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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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Vol. 20 No. 2 (2022)

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Review Articles

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