New heterocyclic systems derived from pyridine: new substrates for the investigation of the azide/tetrazole equilibrium

By exploiting the reactivity of 7-alkyl-3-chloro-4-cyano-1-hydrazino-5,6,7,8-tetrahydro-2,7-naphthyridines 5 some 7-alkyl-1-azido-3-chloro-4-cyano-5,6,7,8-tetrahydro-2,7-naphthyridines 6 were synthesized. Looking at their chemical properties we have ascertained that in these compounds the azide/tetr...

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Published in:Tetrahedron 2014-11, Vol.70 (45), p.8648-8656
Main Authors: Sirakanyan, Samvel N., Spinelli, Domenico, Geronikaki, Athina, Hovakimyan, Anush A., Noravyan, Azat S.
Format: Article
Language:English
Subjects:
5,6,7,8-Tetrahydro-2,7-naphthyridines
Azide–tetrazole equilibrium
Chlorine
New tetraheterocyclic systems
Nitriles
Nucleophilic substitution
Pyrazole
Pyridines
Rings (mathematics)
Tetrahedrons
Tetrazoles
Thiophenes
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container_end_page 8656
container_issue 45
container_start_page 8648
container_title Tetrahedron
container_volume 70
creator Sirakanyan, Samvel N.
Spinelli, Domenico
Geronikaki, Athina
Hovakimyan, Anush A.
Noravyan, Azat S.
description By exploiting the reactivity of 7-alkyl-3-chloro-4-cyano-1-hydrazino-5,6,7,8-tetrahydro-2,7-naphthyridines 5 some 7-alkyl-1-azido-3-chloro-4-cyano-5,6,7,8-tetrahydro-2,7-naphthyridines 6 were synthesized. Looking at their chemical properties we have ascertained that in these compounds the azide/tetrazole equilibrium is completely shifted towards the azido form (both in solid state and in solution). Their behaviour with some amines was tested as well. Moreover by exploiting the reactivity of the chlorine and of the nitrile group we have fused on the pyridine system two new rings (pyrazole or thiophene), thus obtaining previously unknown heterocyclic systems (10 and 11). Interestingly, in these new systems, the position of the above equilibrium is reversed. [Display omitted]
doi_str_mv 10.1016/j.tet.2014.09.047
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subjects 5,6,7,8-Tetrahydro-2,7-naphthyridines
Azide–tetrazole equilibrium
Chlorine
New tetraheterocyclic systems
Nitriles
Nucleophilic substitution
Pyrazole
Pyridines
Rings (mathematics)
Tetrahedrons
Tetrazoles
Thiophenes
title New heterocyclic systems derived from pyridine: new substrates for the investigation of the azide/tetrazole equilibrium
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