Abstract
A new type of isatin analog-2,3-dioxo-2,3-dihydro-4-methyl-6-chloro-1H-pyrrolo[2,3-b]pyridine — was obtained by oxidation of 4-methyl-6-chloro-1H-pyrrolo(2,3-b]pyridine. Condensation of L-arabinose with 4-methyl-6-chloro-2,3-dihydropyrrolo[2,3-b]pyridine and subsequent acetylation and dehydrogenation gave 1-(2,3,4-tri-O-acetyl-α-L-arabinopyranosyl)-4-methyl-6-chloropyrrolo[2,3-b]pyridine, which served as the starting compound for the synthesis of 1-α-L-arabinopyranosyl-4-methyl-6-chloropyrrolo[2,3-b]pyridine. Oxidation of 1-(2,3,4-tri-O-acetylα-L-arabinopyranosyl)-4-methyl-6-chloropyrrolo[2,3-b]pyridine gave 1-(2,3.4-tri-O-acetyl-α-L-arabinopyranosyl)-2,3-dioxo-2,3-dihydro-4-methyl-6-chloropyrrolo [2,3-b]pyridine.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
I. V. Yartseva, L. V. Éktova, M. N. Preobrazhenskaya, N. A. Lesnaya, N. P. Yavorskaya, G. N. Platonova, and Z. P. Sof'ina, Bioorg. Khim., 1, 1589 (1975).
M. N. Preobrazhenskaya, T. D. Miniker, V. S. Martynov, L. N. Yakhontov, N. P. Kostyuchenko, and D. M. Krasnokut-skaya, Zh. Org. Khim., 10, 745 (1974).
M. N. Preobrazhenskaya, T. D. Miniker, V. S. Martynov, L. N. Yakhontov, and D. M. Krasnokut-skaya, Zh. Org. Khim., 10, 2449 (1974).
L. N. Yakhontov, M. Ya. Uritskaya, and M. V. Rubtsov, Zh. Org. Khim., 34, 1449 (1964).
V. N. Tolkachev and M. N. Preobrazhenskaya, Zh. Org. Khim., 11, 658 (1975).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1083–1086, August, 1977.
Rights and permissions
About this article
Cite this article
Éktova, L.V., Miniker, T.D., Yartseva, I.V. et al. Synthesis of 2,3-dioxo-2,3-dihydro-4-methyl-6-chloro-1H-pyrrolo[2,3-b]pyridine and its 1-α-L-arabinopyranoside. Chem Heterocycl Compd 13, 872–874 (1977). https://doi.org/10.1007/BF00488913
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00488913