Convenient variant of the synthesis of 5-oxo-4,5-dihydro-1h-[1,2,3]triazolo[4,5-b]pyridine-6-carboxylic acid

Syrota, Natalia А.; Kemskii, S. V.; Vovk, M. V.

doi:10.30970/vch.6201.191

Cited by 1 publication

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“…However, the use of Meldrum's acid (3), a synthetic equivalent of malonic acid, in this process under similar reaction conditions is much more productive since it increases the yield of the target compounds to 91 -94 % (Method B). The likely transformation scheme in the case of malonic acid is through intermediate products A and B, while in the case of Meldrum's acid it is through C and D. Indeed, the efficiency of the latter is due to the structure of intermediate D which, in contrast to intermediate B, is characterized by much higher selectivity of further transformation [20].…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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

СИРОТА

Kemskiy

Saliyeva

et al. 2022

J. Org. Pharm. Chem.

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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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Section: ■ Results and Discussionmentioning

confidence: 99%