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NEW HETEROCYCLIC SYSTEMS BASED ON 1-HYDRAZINO-5,6,7,8-TETRAHYDRO[2,7]NAPHTHYRIDINE: 7,8,9,10-TETRAHYDRO[1,2,4]TRIAZOLO[3,4-a]- AND 7,8,9,10-TETRAHYDRO[1,2,4]TRIAZOLO[5,1-a][2,7]NAPHTHYRIDINES

С. Н. Сираканян, Н. Г. Аветисян, А. С. Норавян
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Abstract


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.

Authors: S. N. Sirakanyan, N. G. Avetisyan, and A. S. Noravyan.

English Translation in Chemistry of Heterocyclic Compounds, 2012, 48 (3), pp 470-475

http://link.springer.com/article/10.1007/s10593-012-1017-z


Keywords


5,6,7,8-tetrahydro[2,7]naphthyridines; 7,8,9,10-tetrahydro[1,2,4]triazolo[3,4-a][2,7]naphthyridines; 7,8,9,10-tetrahydro[1,2,4]triazolo[5,1-a][2,7]naphthyridines; nucleophilic substitution; Dimroth rearrangement

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