Thermal rearrangement of 3-​acylisoxazole arylhydrazones allowed facile preparation of 2H- ​1,2,3-​triazoles which were firstly reacted with isoamyl nitrite and then with an opportune arylhydrazine to produce the corresponding a-​hydroxyiminohydrazones 8a-​h. The reaction of compounds 8a-​h with phosphorus pentachloride afforded the desired 4,4'-​bitriazoles 1a-​h. The a-​hydroxyiminoketone derivative 7 or the a-​diketone 14 reacted easily with 1,2- phenylenediamine to afford 1,2,3-​triazoles 2a-​c bearing the quinoxaline moiety at position 4. Improved yields of the quinoxalines 2a-​c were obtained when 1,2-​phenylenediamine was reacted with the dioxime 15.

Synthesis of new 2,2 '-disubstituted 5,5 '-dimethyl-4,4 '-bitriazoles and 2-(4-triazolyl)quinoxalines

SIMONI, Daniele;RONDANIN, Riccardo
2000

Abstract

Thermal rearrangement of 3-​acylisoxazole arylhydrazones allowed facile preparation of 2H- ​1,2,3-​triazoles which were firstly reacted with isoamyl nitrite and then with an opportune arylhydrazine to produce the corresponding a-​hydroxyiminohydrazones 8a-​h. The reaction of compounds 8a-​h with phosphorus pentachloride afforded the desired 4,4'-​bitriazoles 1a-​h. The a-​hydroxyiminoketone derivative 7 or the a-​diketone 14 reacted easily with 1,2- phenylenediamine to afford 1,2,3-​triazoles 2a-​c bearing the quinoxaline moiety at position 4. Improved yields of the quinoxalines 2a-​c were obtained when 1,2-​phenylenediamine was reacted with the dioxime 15.
2000
Invidiata, F. P.; Aiello, S.; Furno', G.; Aiello, E.; Simoni, Daniele; Rondanin, Riccardo
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11392/1209302
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