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Organic azides in heterocyclic synthesis, 14. Synthesis of 3,6‐diaminopyridazine from 6‐azidotetrazolo[1,5‐ b ]pyridazine
Author(s) -
Deeb Ali,
Sterk Heinz,
Kappe Thomas
Publication year - 1991
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1991199101210
Subject(s) - pyridazine , chemistry , yield (engineering) , derivative (finance) , medicinal chemistry , boiling point , organic chemistry , boiling , materials science , economics , financial economics , metallurgy
6‐Azidotetrazolo[1,5‐ b ]pyridazine („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°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 .