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.
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M. Gall, R. A. Lahti, A. D. Rudzik, D. J. Duchamp, C. Chidester, and T. Scahill, J. Med. Chem., 21, 542 (1978).CrossRefGoogle Scholar
B. S. Holla, K. N. Poojary, B. Kalluraya, and P. V. Gowda, Farmaco, 51, 793 (1996).Google Scholar
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).CrossRefGoogle Scholar
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.Google Scholar
C. J. Shishoo, M. B. Devani, G. V. Ullas, S. Ananthan, and V. S. Bhadti, J. Heterocycl. Chem., 18, 43 (1981).CrossRefGoogle Scholar
1.The Scientific Technological Center of Organic and Pharmaceutical Chemistry of National Academy of Sciences of the Republic of Armenia, A. L. Mnjoyan Institute of Fine Organic ChemistryYerevanArmenia