Tetrazine

Related molecular formulas
C2H4N4
CN4 C2H2N4 C3H4N4
C2N4
C2HN3 C2H3N5
Not to be confused with tetrazene.

Tetrazine is a compound that consists of a six-membered aromatic ring containing four nitrogen atoms with the molecular formula C2H2N4. The name tetrazine is used in the nomenclature of derivatives of this compound. Three core-ring isomers exist: 1,2,3,4-tetrazines, 1,2,3,5-tetrazines, and 1,2,4,5-tetrazines, also known as v-tetrazines, as-tetrazines and s-tetrazines respectively.[1]

1,2,3,4-Tetrazines

1,2,3,4-Tetrazines are often isolated fused to an aromatic ring system and are stabilized as the dioxide derivatives.

1,2,4,5-Tetrazines

1,2,4,5-Tetrazines are very well known and myriad 3,6-disubstituted 1,2,4,5-tetrazines are known.[2] These materials are of use in the area of energetic chemistry.

Heavily substituted tetrazines form the verdazyls, a family of stable radicals.[3]

Protected tetrazines are strong acetylene acceptors in Diels-Alder equilibria. For example, dipyridinyl 1,2,4,5-tetrazine abstracts acetylene from norbornadiene to cyclopentadiene and a pyridazine:[4] 1,2,4,5-tetrazines are widely used in bioorthogonal chemistry as part of inverse electron demand diels alder (IEDDA) reactions due to their biocompaibility and the degree of orthogonality they provide to other commonly used reactions such as click chemistry (CuAAC or SPAAC).[5][6]

With norbornadiene fused to an arene the reaction stops at an intermediary stage.[7]

See also

Wikimedia Commons has media related to Tetrazines.
  • 6-membered rings with one nitrogen atom: pyridine
  • 6-membered rings with two nitrogen atoms: diazines
  • 6-membered rings with three nitrogen atoms: triazines
  • 6-membered rings with five nitrogen atoms: pentazine
  • 6-membered rings with six nitrogen atoms: hexazine

References

  1. ^ Alvarez-Builla, Julio; Jose Vaquero, Juan; Barluenga, José (2011). Modern Heterocyclic Chemistry. Wiley-VCH. p. 1778. ISBN 978-3527332014.
  2. ^ (see United States Patent 6645325)
  3. ^ Hicks, Robin G. (2010). "Verdazyls and related radicals containing the hydrazyl [R2N–NR] group". In Hicks, Robin G. (ed.). Stable Radicals. Wiley. pp. 246–264. ISBN 978-0-470-77083-2.
  4. ^
    • Dalkılıç, Erdin, and Arif Daştan. "Synthesis of cyclopentadiene derivatives by retro-Diels–Alder reaction of norbornadiene derivatives." Tetrahedron 71.13 (2015): 1966-1970.
    • Dalkılıç, Erdin, et al. "Novel and versatile protocol for the preparation of functionalized benzocyclotrimers." Tetrahedron Letters 50.17 (2009): 1989-1991.
  5. ^ Saracoglu, Nurullah (May 2007). "Recent advances and applications in 1,2,4,5-tetrazine chemistry". Tetrahedron. 63 (20): 4199–4236. doi:10.1016/j.tet.2007.02.051. ISSN 0040-4020.
  6. ^ Bird, Robert E.; Lemmel, Steven A.; Yu, Xiang; Zhou, Qiongqiong Angela (2021-12-15). "Bioorthogonal Chemistry and Its Applications". Bioconjugate Chemistry. 32 (12): 2457–2479. doi:10.1021/acs.bioconjchem.1c00461. ISSN 1043-1802.
  7. ^ π-Bond Screening in Benzonorbornadienes: The Role of 7-Substituents in Governing the Facial Selectivity for the Diels-Alder Reaction of Benzonorbornadienes with 3,6-Di(2-pyridyl)-s-Tetrazine. Ronald N. Warrener and Peter A. Harrison Molecules 2001, 6, 353–369 Online Article
This article is issued from Wikipedia. The text is available under Creative Commons Attribution-Share Alike 4.0 unless otherwise noted. Additional terms may apply for the media files.