1,2,3-Триазол-4(5)-аміни – зручні синтетичні блоки для конструювання триазолоанельованих гетероциклів

• Date: 2022
• Main Authors: Syrota, Natalia O., Kemskiy, Sergiy V., Saliyeva, Lesya M., Vovk, Mykhailo V.
• Format: Article
• Language: English
• Published: National University of Pharmacy 2022
• Subjects: 4(5)-аміно-1,2,3-триазоли; триазоло[4,5-b]піридини; триазоло[4,5-d]піримідини; триазолоанельовані азепіни; циклоконденсація
• Online Access: https://ophcj.nuph.edu.ua/article/view/258512
• Journal Title: Journal of Organic and Pharmaceutical Chemistry

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.