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Organic azides in heterocyclic synthesis, 14. Synthesis of 3,6-diaminopyridazine from 6-azidotetrazolo[1,5-b]pyridazine

✍ Scribed by Deeb, Ali ;Sterk, Heinz ;Kappe, Thomas

Publisher
John Wiley and Sons
Year
1991
Tongue
English
Weight
311 KB
Volume
1991
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

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.

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