Synthesis and alkylation of some [1,2,4]triazolo[4,3-b]tetrazines

Arkivoc

Volumn 2000, Issue 3 SPEC.ISS., 2000, Pages 259-265

  Novák, Zoltán ^a   Csámpai, Antal ^a   Kotschy, András ^a  

^a EÖTVÖS LORÁND UNIVERSITY   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

6 (3,5 DIMETHYLPYRAZOL 1 YL)[1,2,4]TRIAZOLO[4,3 B][1,2,4,5]TETRAZINIUM TETRAFLUOROBORATE; 6 (MORPHOLIN 4 YL)[1,2,4]TRIAZOLO[4,3 B][1,2,4,5]TETRAZINIUM TETRAFLUOROBORATE; 6 (MORPHOLINO 4 YL)[1,2,4]TRIAZOLO[4,3 B][1,2,4,5]TETRAZINE; [1,2,4]TRIAZOLO[4,3 B][1,2,4,5]TETRAZINE; [1,2,4]TRIAZOLO[4,3 B]TETRAZINE; REAGENT; TETRAFLUOROBORATE; TETRAZINE DERIVATIVE; TRIAZOLOTETRAZINIUM; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CALCULATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; QUANTUM CHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 13544268619     PISSN: 14246376     EISSN: 14246376     Source Type: Journal    
DOI: None     Document Type: Article

References (11)

1. Hajós, Gy.; Kotschy, A. Acta Chimica Slovenica, 1998, 45, 285
2. Kotschy, A.; Hajós, Gy.; Messmer, A.; Jones, G. Tetrahedron 1996, 52, 1399 and references therein.
3. Kotschy, A.; Hajós, Gy.; Messmer, A, J. Org. Chem. 1995, 60, 4919
4. Jones, G.; Richardson, C.M.; Yates, P.C.; Hajós, Gy.; Timári, G. Tetrahedron, 1993, 49, 4307
5. Kotschy, A.; Novák, Z.; Vincze, Z.; Smith, D.M.; Hajós, Gy. Tetrahedron Lett., 1999, 40, 6313 and references therein.
6. (a) Chavez, D.E.; Hiskey, M.A. J. Heterocycl. Chem., 1998, 35, 1329
7. (b) Ershov, V.A.; Postovskii, LY. Khim. Geterosikl. Soedin., 1968, 4, 1134
8. Glidewell, C.; Lightfoot, P.; Royles, B.J.L.; Smith, D.M., J. Chem. Soc., Perkin Trans. 2, 1997, 1167
9. The tetrafluoroborate salts were found to be superior to other analogues both in terms of their stability and crystallisation ability. See also Ref. 1.
10. Calculations were carried out with the Gaussian98w program package. Geometries were optimised on the ab initio level using the 3-21G basis set.
11. The first molecular orbital with a considerable contribution from the "in plane" atomic orbitale of any of the triazole nitrogens, lies at 1.88 eV (3) and 1.83 eV (6) below the HOMO orbital, far too low to make their effect substantial.