Methods have been developed for the synthesis of new substituted 7,8,9,10-tetrahydro[1,2,4]triazolo-[3,4-a][2,7]naphthyridines from 3-chloro-1-hydrazino-7-methyl-5,6,7,8-tetrahydro-[2,7]naphthyridine-4-carbonitrile. It was shown that on heating in an amine (ethanolamine, pyrrolidine, 2-hydroxy-propylamine), they undergo a Dimroth rearrangement at the triazole fragment, being converted into 7,8,9,10-tetrahydro[1,2,4]triazolo[5,1-a][2,7]naphthyridine derivatives.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
M. Gall, R. A. Lahti, A. D. Rudzik, D. J. Duchamp, C. Chidester, and T. Scahill, J. Med. Chem., 21, 542 (1978).
B. S. Holla, K. N. Poojary, B. Kalluraya, and P. V. Gowda, Farmaco, 51, 793 (1996).
T. Ukita, Y. Nakamura, A. Kubo, Y. Yamamoto, Y. Moritani, K. Saruta, T. Higashijima, J. Kotera, K. Fujishige, M. Tagaki, K. Kikkawa, and K. Omori, Bioorg. Med. Chem. Lett., 13, 2341 (2003).
S. N. Sirakanyan, V. G. Kartsev, E. G. Paronikyan, and A. S. Noravyan, in: Nitrogen-containing Heterocycles [in Russian], Vol. 1, ICSPF, Moscow (2006), p. 453.
C. J. Shishoo, M. B. Devani, G. V. Ullas, S. Ananthan, and V. S. Bhadti, J. Heterocycl. Chem., 18, 43 (1981).
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 500–505, March, 2012.
Rights and permissions
About this article
Cite this article
Sirakanyan, S.N., Avetisyan, N.G. & Noravyan, A.S. New heterocyclic systems based on 1-hydrazino-5,6,7,8-tetrahydro[2,7]naphthyridine: 7,8,9,10-tetra-hydro[1,2,4]triazolo[3,4-a]- and 7,8,9,10-tetra-hydro[1,2,4]triazolo[5,1-a][2,7]naphthyridines. Chem Heterocycl Comp 48, 470–475 (2012). https://doi.org/10.1007/s10593-012-1017-z
Received:
Revised:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-012-1017-z