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Synlett 2015; 26(04): 557-560
DOI: 10.1055/s-0034-1379615
letter
© Georg Thieme Verlag Stuttgart · New York

1,2,4,5-Tetrazinyl-Substituted Amino-1,2,4,5-Tetrazines

Megan M. Breiner
a   Los Alamos National Laboratory, Weapons Experiments Division, Los Alamos, NM 87545, USA
,
David E. Chavez*
a   Los Alamos National Laboratory, Weapons Experiments Division, Los Alamos, NM 87545, USA
,
Thomas W. Myers
a   Los Alamos National Laboratory, Weapons Experiments Division, Los Alamos, NM 87545, USA
,
Richard D. Gilardi
b   Naval Research Laboratory, Laboratory for the Structure of Matter, Washington, DC 20375, USA   eMail: dechavez@lanl.gov
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Publikationsverlauf

Received: 18. Oktober 2014

Accepted: 06. November 2014

Publikationsdatum:
08. Januar 2015 (online)

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Abstract

The synthesis of 1,2,4,5-tetrazinylamino-1,2,4,5-tetrazines is reported, including the preparation of compounds containing three tetrazine heterocycles in a single compound. These materials were compared to phenylamine derivatives, also synthesized in this study. The UV/Vis and cyclic voltammetry data were collected and are reported, along with the crystal structure of one of the tritetrazine compounds.

Key words

tetrazines - heterocycle - cyclic voltammetry - UV/Vis - nucleophilic addition

Supporting Information

    Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1379615.
  • Supporting Information
 

  • References and Notes

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  • 11 See the Supporting Information for further details of the experimental procedures.
  • 12 Compound 11; Typical Procedure: Compound 1 (270 mg, 1.0 mmol) was placed in a 50 mL round-bottomed flask. MeCN (10 mL) was added. 1,4-Phenylenediamine (54 mg, 0.5 mmol) was added and the reaction was heated to reflux for 1 h. The reaction was allowed to cool to ambient temperature and the precipitate was isolated by filtration. The product was washed with cold MeCN, and air-dried to give 189 mg of a purple solid (83% yield); mp 299 °C (dec.). 1H NMR (300 MHz, DMSO-d 6): δ = 2.24 (s, 6 H), 2.45 (s, 6 H), 7.77 (s, 4 H), 11.03 (s, 1 H). 13C NMR (100 MHz, DMSO-d 6): δ = 12.54, 13.35, 108.95, 120.58, 133.81, 141.62, 150.46, 156.93, 160.37. IR (KBr): νmax = 3406, 3256, 3163, 3105, 2915, 1587, 1563, 1505, 1475, 1417, 1215 cm–1. Anal. Calcd for C20H20N14: C, 52.62; H, 4.42, N, 42.96. Found: C, 52.63; H, 4.40; N, 42.95.
  • 13 CCDC 1028515 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.