135710-46-2Relevant academic research and scientific papers
Organic Azides in Heterocyclic Synthesis, 14. Synthesis of 3,6-Diaminopyridazine from 6-Azidotetrazolopyridazine
Deeb, Ali,Sterk, Heinz,Kappe, Thomas
, p. 1225 - 1227 (2007/10/02)
6-Azidotetrazolopyridazine ("3,6-Diazidopyridazine", 1) reacts at ambient temperature with phosphanes or phosphites 2a - c to yield the phosphazenes 3a - c.In contrast to literature reports, the tetrazolopyridazines 1, and 3a,b react with phosphanes to yield 3,6-bis(phosphoranylideneamino)pyridazines 4; however, the required temperature is rather high (180 deg C).The use of phosphites instead of phosphanes leads to "Michaelis-Arbuzov-type" rearrangements; thus, 3a reacts in boiling 2d to afford 6, and heating of the trimethoxyphosphazene 3c in refluxing 1,2-dichlorobenzene yields the methylamino derivative 7.Key words: Staudinger reaction / Phosphanes / Phosphites / Phosphazenes / Amidophosphonates
