Synthesis of substituted 5H-imidazo[1,2-e][1,3,5]triazepines
DOI:
https://doi.org/10.15407/dopovidi2020.04.085Keywords:
2-(aminomethyl)imidazole, 2-e][1, 3, 3-butadienes, 5]triazepines, imidazo[1, regioselective annulation, tetrachloro-2-aza-1Abstract
A preparative method for the synthesis of previously unknown substituted 5H-imidazo[1,2-e][1,3,5]triazepines was developed based on the available reagents. Thus, the interaction of aromatic acid amides with chloral leads to chloralamides, which are subsequently converted into imidoylchlorides by the action of phosphorus pentachloride. The latter, when treated with triethylamine, give tetrachloro-2-aza-1,3-butadiene. The interaction of them with 2-(aminomethyl)imidazole proceeds regioselectively on the primary amino group with the formation of intermediates, the prototropy of which promotes the intramolecular heterocyclization with the participation of the imidoyl chloride moiety and the endocyclic nitrogen atom of the imidazole. As a result of all these transformations, a regioselective annulation to the imidazole of the triazepine cycle occurs to give in high yields the first representatives of the new 5H-imidazo[1,2-e][1,3,5]triazepine heterocyclic system. Their structure was reliably proven with the help of the modern spectral studies and X-ray diffraction analysis.
Downloads
References
Swahn, B.-M., Holenz, J., Kihlström, J., Kolmodin, K., Lindström, J., Plobeck, N., Rotticci, D., Sehgelmeble, F., Sundström, M., Berg, S., Fälting, J., Georgievska, B., Gustavsson, S., Neelissen, J., Ek, M., Olsson, L.-L. & Berg, S. (2012). Aminoimidazoles as BACE-1 inhibitors: The challenge to achieve in vivo brain efficacy. Bioorg. Med. Chem. Lett., No. 22, pp. 1854-1859. Doi: https://doi.org/10.1016/j.bmcl.2012.01.079
Zhang, H., Khalil, Z., Conte, M. M., Plisson, F. & Capon, R. J. (2012). A search for kinase inhibitors and antibacterial agents: bromopyrrolo-2-aminoimidazoles from a deep-water Great Australian Bight sponge, Axinella sp. Tetrahedron Lett., No. 53, pp. 3784-3787. Doi: https://doi.org/10.1016/j.tetlet.2012.05.051
Chiriano, G., De Simone, A., Mancini, F., Perez, D. I., Cavalli, A., Bolognesi, M. L., Legname, G., Martinez, A., Andrisano, V., Carloni, P. & Roberti, M. (2012). A small chemical library of 2-aminoimidazole derivatives as BACE-1 inhibitors: Structure-based design, synthesis, and biological evaluation. Eur. J. Med. Chem., No. 48, pp. 206-213. Doi: https://doi.org/10.1016/j.ejmech.2011.12.016
Ghanem, N. M., Farouk, F., George, R. F., Abbas, S. E. S. & El-Badry, O. M. (2018). Design and synthesis of novel imidazo[4,5-b]pyridine based compounds as potent anticancer agents with CDK9 inhibitory activity. Bioorg. Chem., No. 80, pp. 565-576. Doi: https://doi.org/10.1016/j.bioorg.2018.07.006
Smejkal, T., Hachisu, S., Scutt, J. N., Willetts, N. J., Sayer, D., Wildsmith, L., Oliver, S., Thompson, C. & Muehlebach, M. (2018). Herbicidal aryldiones incorporating a 5-methoxy-[1,2,5]triazepane ring. Bioorg. Med. Chem. Lett., No. 28, pp. 339-343. Doi: https://doi.org/10.1016/j.bmcl.2017.12.042
Rodrigues, T., Prudencio, M., Moreira, R., Mota, M. M. & Lopes, F. (2012). Targeting the liver stage of malaria parasites: a yet unmet goal. J. Med. Chem., No. 55, pp. 995-1012. Doi: https://doi.org/10.1021/jm201095h
Zeydi, M. M. & Mahmoodi, N. O. (2017). Overview on developed synthesis methods of triazepane heterocycles. J. Chin. Chem. Soc., 64, No. 9, pp. 1023-1034. Doi: https://doi.org/10.1002/jccs.201700069
Elattar, K. M., Abozeid, M. A. & Etman, H. A. (2015). Developments in 1,2,5-triazepines chemistry: reactions and synthetic applications. Synth. Commun., No. 46, pp. 93-117. Doi: https://doi.org/10.1080/00397911.2015.1109126
Komodziński, K., Lepczyńska, J., Ruszkowski, P., Milecki, J. & Skalski, B. (2013). Biological evaluation of an imidazole-fused 1,3,5-triazepinone nucleoside and its photochemical generation via a 6-azidopurine modified oligonucleotide. Tetrahedron Lett., No. 54, pp. 3781-3784. Doi: https://doi.org/10.1016/j.tetlet.2013.05.051
Foldesi, T., Dancso, A., Simig, G., Volk, B. & Milen, M. (2016). Efficient synthesis of a new compound family, 9-aryl-5H-imidazo[2,1-d][1,2,5]triazepin-6(7H)-ones. Tetrahedron, No. 72, pp. 5427-5432. Doi: https://doi.org/10.1016/j.tet.2016.07.029
Drach, B. S., Коvаlеv, V. А. & Кirsаnоv, А. V. (1975). Reaction of acid chlorides of N-1,2,2,2-tetrachloroethyl-, N-perchlorovinyl- and N-perchloroethyliminobenzoic acids with amines. Zhurn. Оrgan. Khimii, 11, No. 1, pp. 122-127 (in Russian). Doi: https://doi.org/10.1002/chin.197514187
Drach, B. S., Коvаlеv, V. А. & Кirsаnоv, А. V. (1976). Cyclization reactions of N-perchlorovinyliminocarboxylic acid chlorides with nucleophiles. Zhurn. Оrgan. Khimii, 12, No. 3, pp. 673–678 (in Russian).
Drach, B. S. & Коvаlеv, V. А. (1976). Chlorides of N 1-chloroalkyl- and N 1-chloro-1-alkenyliminobenzoic acids. Zhurn. Оrgan. Khimii, 12, No. 11, pp. 2319-2325 (in Russian).
Demydchuk, B. A., Rusanov, E. B., Rusanova, J. A. & Brovarets, V. S. (2017). Regioselective synthesis of bicyclic 1,3,5-triazepine system starting from tetrachloro-2-aza-1,3-butadienes. Curr. Chem. Lett., 6, No. 2, pp. 49-54. Doi: https://doi.org/10.5267/j.ccl.2017.2.001
Demydchuk, B. A., Gakh, A. A., Brovarets, V. S., Chernega, A. N., Rusanov, E. B. & Drach, B. S. (2006). Regioselective annulation of seven-, eight-, and nine-membered azaheterocycles to benzimidazole starting from chloro-substituted 2-aza-1,3-dienes. Synthesis., No. 14, pp. 2323-2326. Doi: https://doi.org/10.1055/s-2006-942453
Downloads
Published
How to Cite
Issue
Section
License
Copyright (c) 2023 Reports of the National Academy of Sciences of Ukraine
This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.
