Csilla Sepsey Für, Gergő Riszter, Áron SzigetvárI, Miklós Dékány, György Keglevich, László HazaI, Hedvig BölcskeI
Molecules (Basel, Switzerland) 2021 Apr 08In orderto synthesize new pyridazine derivatives anellated with different nitrogen heterocyclic moieties, spiro[cycloalkane]pyridazinones were transformed into the corresponding thioxo derivatives via a reaction with phosphorus pentasulfide. The reaction of the formed 2,3-diazaspiro[5.5] undec-3-ene-1-thiones with hydrazine provided the corresponding 1-hydrazono-2,3-diazaspiro[5.5] undec-3-ene, whose diazotization led to the desired spiro[cyclohexane-1,8'-tetrazolo[1,5-b]pyridazines. The reaction of dihydropyridazinethiones with benzhydrazide afforded the corresponding 7H-spiro[[1,2,4]triazolo[4,3-b]pyridazin-8,1'-cyclohexanes]. As a result of our work, seven new pyridazinethione intermediates were prepared, which served as starting materials for the synthesis of two kinds of new ring systems: tetrazolo-pyridazines and triazolo-pyridazines. The six new annulated derivatives were characterized by physicochemical parameters. The new N-heterocycles are valuable members of the large family of pyridazines.
Csilla Sepsey Für, Gergő Riszter, Áron SzigetvárI, Miklós Dékány, György Keglevich, László HazaI, Hedvig BölcskeI. Novel Ring Systems: Spiro[Cycloalkane] Derivatives of Triazolo- and Tetrazolo-Pyridazines. Molecules (Basel, Switzerland). 2021 Apr 08;26(8)
PMID: 33917797
View Full Text