Triazenes

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Hodgkin's lymphoma.[1]

Triazenes are organic compounds that contain the functional group R1−N=N−NR2R3, where the R are each any of various types of substituent groups.[2] Some anti-cancer medications and dyes are triazenes.[3] Formally, the triazenes are related to the unstable chemical triazene, H2N−N=NH.

Production

Triazenes are prepared from the N-coupling reaction between

diazonium salts and primary or secondary amines.[4] The coupling reactions are typically mild, using a base such as sodium acetate,[5] sodium carbonate,[5] or sodium bicarbonate.[4]

The diazonium reagents are themselves available starting from amines. For symmetrical triazenes derived from primary amines, partial diazotization gives a mixture of the original amine and its diazo derivative that then couple with each other. For example,

one-pot reaction.[5][6]
For asymmetrical triazenes, for example (phenyldiazenyl)pyrrolidine (PhN=N−NC4H8), the diazonium salt must be pre-made.

Azo N-coupling

Analogues of Tröger's base containing a symmetric pair of asymmetric triazene side-chains have been obtained similarly.[7]

Bis-triazene analogue of Tröger's base

Reactions and applications

Triazenes derived from

tautomerism
. In the case of symmetric triazenes, the tautomers are identical.

Tautomerism of triazenes derived from primary amines

Triazenes can be converted to

diazonium salts.[8]

Triazenes used in the synthesis of thiophenols

Triazenes decompose in the presence of protonating or alkylating agents into

secondary amines is based on this principle.[9]

Polymeric triazenes are applied as conductive and absorbent materials.[10] Triazenes have been used in the synthesis of cinnoline, functionalized lactams, and coumarins.[9][8]

References

  1. ^ "Dacarbazine". The American Society of Health-System Pharmacists. Archived from the original on 11 September 2017. Retrieved 8 December 2016.
  2. ISSN 1433-7851
    .
  3. ISBN 978-3527306732
    .
  4. ^
    doi:10.15227/orgsyn.079.0052
    .
  5. ^
    S2CID 196805424
    .
  6. doi:10.15227/orgsyn.014.0024.{{cite journal}}: CS1 maint: multiple names: authors list (link
    )
  7. S2CID 99294625
    .
  8. ^
    PMID 12298030
    .
  9. ^
    doi:10.1055/s-1999-2803
    .
  10. doi:10.1002/app.39069
    .
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