Abstract
Condensation of 5- or 6-nitroindoline with L-arabinose gave 1-α-L-arabinopyranosyl-5 (or 6)-nitroindolines, which, after acetylation, dehydrogenation, and removal of the protective groups, are converted to 1-α-L-arabinopyranosyl-5(or 6)-nitroindoles and then to the corresponding amino derivatives. 1-α-L-Arabinopyranosyl-6-nitro-3-bromo-(iodo)indoles were obtained. The selective 2′-O- and 3′-O-deacetylation of 1-(2′, 3′, 4′-tri-O-acetyl)-α-L-arabinopyranosyl-6-nitroindole was accomplished.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
M. N. Preobrazhenskaya, Khim.-Farm. Zh., 5, 139 (1976).
M. N. Preobrazhenskaya, Usp. Khim., 36, 1760 (1967).
L. J. Dolby and D. Boath, J. Am. Chem. Soc., 88, 1049 (1966).
A. J. Fatiadi, Synthesis, 229 (1974).
P. Julien, A. M. Meyer, and A. Prunty, in: Heterocyclic Compounds (edited by R. Elderfield), Vol. 3, Wiley, New York (1953).
M. N. Preobrazhenskaya, V. N. Tolkachev, N. K. Geling, and N. P. Kostyuchenko, Zh. Org. Khim., 10, 1764 (1974).
A. P. Terent'ev, M. N. Preobrazhenskaya, A. S. Bobkov, and G. M. Sorokina, Zh. Obshch. Khim., 29, 2541 (1959).
A. A. Magnin, A. M. Stephen, and R. J. H. Davis, Tetrahedron, 28, 3069 (1972).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 224–229, February, 1979.
Rights and permissions
About this article
Cite this article
Mukhanov, V.I., Yartseva, I.V., éktova, L.V. et al. Synthesis and study of L-arabinopyranosides of 5- and 6-nitroindoles. Chem Heterocycl Compd 15, 188–193 (1979). https://doi.org/10.1007/BF00480365
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00480365