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-<i>a</i>]- AND 7,8,9,10-TETRAHYDRO[1,2,4]TRIAZOLO[5,1-<i>a</i>][2,7]NAPHTHYRIDINES

Authors

  • С. Н. Сираканян 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 Chemistry
  • Н. Г. Аветисян 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 Chemistry
  • А. С. Норавян 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 Chemistry

DOI:

https://doi.org/10.1007/1240

Keywords:

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

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

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Published

2013-11-26

Issue

No. 3 (2012)

Section

Original Papers