Chemistry of Heterocyclic Compounds

, Volume 48, Issue 3, pp 470–475 | Cite as

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

  • S. N. Sirakanyan
  • N. G. Avetisyan
  • A. S. Noravyan

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.


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


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Copyright information

© Springer Science+Business Media, Inc. 2012

Authors and Affiliations

  • S. N. Sirakanyan
    • 1
  • N. G. Avetisyan
    • 1
  • A. S. Noravyan
    • 1
  1. 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

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