Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Download PDF
Synlett 2015; 26(04): 557-560
DOI: 10.1055/s-0034-1379615
DOI: 10.1055/s-0034-1379615
letter
1,2,4,5-Tetrazinyl-Substituted Amino-1,2,4,5-Tetrazines
Authors
Further Information
Publication History
Received: 18 October 2014
Accepted: 06 November 2014
Publication Date:
08 January 2015 (online)
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.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1379615.
- Supporting Information (PDF)
-
References and Notes
- 1a Clavier G, Audebert P. Chem. Rev. 2010; 110: 3299
- 1b Malinge J, Allain C, Brosseau A, Audebert P. Angew. Chem. Int. Ed. 2012; 51: 8534
- 2 Julien-Macchi E, Allain C, Alain-Rizzo V, Dumas-Verdes C, Galmiche L, Audibert J.-F, Desta MB, Pansu RB, Audebert P. New J. Chem. 2014; 38: 3401
- 3 Zhao Y, Li Y, Qin Z, Jiang R, Liu H, Li Y. Dalton Trans. 2012; 41: 13338
- 4 Li Z, Ding J, Song N, Lu J, Tao Y. J. Am. Chem. Soc. 2010; 132: 13160
- 5a Erdmann RS, Takakura H, Thompson AD, River-Molina F, Allgeyer ES, Bewersdorf J, Toomre D, Schepartz A. Angew. Chem. Int. Ed. 2014; 53: 10242
- 5b Rossin R, van Duijnhoven SM. J, Laeppchen T, van den Bosch SM, Robillard MS. Mol. Pharmaceutics 2014; 11: 3090
- 6a Chavez DE, Hiskey MA. J. Pyrotech. 1998; 7: 11
- 6b Chavez DE, Hiskey MA, Huynh MH. V, Naud DL, Son SF, Tappan BC. J. Pyrotechnics 2006; 23: 70
- 6c Chavez DE, Gilardi RD. J. Energ. Mater. 2009; 27: 110
- 6d Hiskey MA, Chavez DE, Naud D. U.S. Patent 6342589, 2002
- 7 Chavez DE, Hanson SK, Veauthier JM. Angew. Chem. Int. Ed. 2013; 52: 6876
- 8a Cutivet A, Lery E, Poillain D. Tetrahedron Lett. 2008; 49: 2748
- 8b Rusinov GL, Ishmetova RI, Ganebnykh IN, Chupakin ON. Heterocycl. Commun. 2006; 12: 99
- 9 Chavez DE, Parrish DA. J. Heterocycl. Chem. 2009; 46: 8890
- 10 Sheremetev AB, Palysaeva NV, Struchkova MI, Suponitsky KY. Mendeleev Commun. 2012; 22: 302
- 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.