Abstract
Pyridoxine derivatives, 3-hydroxy-2-methylpyridine-4- and -5-carbohydrazides, were synthesized according to optimized known procedures, and a method for the synthesis of 5-(hydroxymethyl)-2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridine-6-carbohydrazide was developed. The hydroxymethyl groups in positions 5 and 6 of 2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridine showed different reactivities, and only the 6-hydroxymethyl group was selectively oxidized to aldehyde under mild conditions. The lactone ring in 5,6-dihydrofuro[3,4-b]pyridin-7(5H)-one was found to be stable to nucleophiles. The synthesized hydrazides showed no antimycobacterial activity.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Shtyrlin, N.V., Lodochnikova, O.A., Pugachev, M.V., Madzhidov, T.I., Sysoeva, L.P., Litvinov, I.A., Klimovitskii, E.N., and Shtyrlin, Yu.G., Russ. J. Org. Chem., 2010, vol. 46, p.561.
Pugachev, M.V., Shtyrlin, N.V., Sysoeva, L.P., Nikitina, E.V., Abdullin, T.I., Iksanova, A.G., Ilaeva, A.A., Musin, R.Z., Berdnikov, E.A., and Shtyrlin, Yu.G., Bioorg. Med. Chem., 2013, vol. 21, p. 4388.
Shtyrlin, N.V., Pavelyev, R.S., Pugachev, M.V., Sysoeva, L.P., Musin, R.Z., and Shtyrlin, Yu.G., Tetrahedron Lett., 2012, vol. 53, p. 3967.
Shtyrlin, N.V., Sapozhnikov, S.V., Koshkin, S.A., Iksanova, A.G., Sabirov, A.H., Kayumov, A.R., Nureeva, A.A., Zeldi, M.I., and Shtyrlin, Yu.G., Med. Chem., 2015, vol. 11, p.656.
Isler, O., Gutmann, H., Straub, O., Fust, B., Bohni, E., and Stude, A., Helv. Chim. Acta, 1955, vol. 118, p. 1033.
Isler, O., Gutmann, H., Straub, O., Fust, B., Bohni, E., and Stude, A., Helv. Chim. Acta, 1955, vol. 118, p. 1046.
Korytnyk, W., Kris, E.J., and Singh, R.P., J. Org. Chem., 1964, vol. 29, p.574.
Cohen, A. and Hughes, E., J. Chem. Soc., 1952, p. 4384.
Preziosi, P., Curr. Drug Metab., 2007, vol. 8, p.839.
Fox, H.H. and Gibas, J.T., J. Org. Chem., 1952, vol. 17, p. 1653.
Vinsova, J., Imramovsky, A., Jampilek, J., Monreal, J.F., and Dolezal, M., Anti-Infect. Agents Med. Chem., 2008, vol. 7, p.12.
Palát, K., Collect. Czech. Chem. Commun., 1967, vol. 32, p. 1191.
Harry, L.Y., Losee, K., Martins, J., Holsing, M., Perry, F.M., and Bernstein, J., J. Am. Chem. Soc., 1953, vol. 75, p. 1933.
Shtyrlin, N.V., Lodochnikova, O.A., and Shtyrlin, Yu.G., Mendeleev Commun., 2012, vol. 22, p.169.
Erokhin, V.V., Kul’tural’nye metody diagnostiki tuberkuleza (Cultural Tuberculosis Diagnostics Methods), Tver: Triada, 2008, p. 208.
Author information
Authors and Affiliations
Corresponding author
Additional information
Dedicated to Full Member of the Russian Academy of Sciences
I.P. Beletskaya on her jubilee
Original Russian Text © R.M. Khaziev, N.V. Shtyrlin, O.A. Lodochnikova, N.V. Volobueva, R.V. Chestnova, A.P. Alekseev, E.I. Romanova, K.V. Balakin, Yu.G. Shtyrlin, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 3, pp. 421–425.
Rights and permissions
About this article
Cite this article
Khaziev, R.M., Shtyrlin, N.V., Lodochnikova, O.A. et al. Synthesis and Antimycobacterial Activity of Hydrazides Based on Pyridoxine Derivatives. Russ J Org Chem 54, 426–430 (2018). https://doi.org/10.1134/S1070428018030090
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428018030090