Azulene-substituted pyridines and pyridinium salts. Synthesis and structure. 2. Azulene-substituted pyridinium salts

Journal of Heterocyclic Chemistry

Volumn 44, Issue 1, 2007, Pages 251-260

  Razus, Alexandru C ^a   Birzan, Liviu ^a   Pavel, Claudia ^a   Lehadus, Oana ^a   Corbu, Andreea ^a   Chiraleu, Filip ^a   Enache, Cristian ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Romania)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; AZULENE; PYRIDINE DERIVATIVE; PYRIDINIUM DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; REACTION ANALYSIS; REPRODUCIBILITY; RING OPENING; SYNTHESIS; THERMODYNAMICS;

EID: 36749000986     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570440143     Document Type: Article

References (16)

1. A. C. Razus, L. Birzan, C. Pavel, O. Lehadus, A. Corbu, F. Chiraleu and C. Enache, J. Heterocycl. Chem., 44, 245 (2007).
2. A. C. Razus, L. Birzan, C. Pavel, O. Lehadus, A. C. Corbu, C. Enache, J. Heterocycl. Chem., 43, 963, (2006).
3. W. Schroth, W. Dolling and A. T. Balaban in Methoden der. Organischen Chemie (Houben-Weyl), Vol. E7 bII, Hrsgb. RP Krehcr, ed, Stuttgart, New York: Georg Thieme Verlag, 1976, pp. 972-977;
4. [b] For the reaction of 4,6,8-triphenyl-pyranylium salts with amine the reported time for the step (a) was several minutes and for the step (b) several hours: ref. [3a] and S. A. Said and A. Fiksdahl, Tetrahedron Asymm., 12, 1947, (2001).
5. A. R. Katritzky, J. M. Lloyd and R. C. Patel J. Chem. Soc. Perkin Trans 1, 1982, 117;
6. A. R. Katritzky, R. H. Manzo, J. M. Lloyd and R. C. Patel Angew. Chem., 92, 867, (1980);
7. A. R. Katritzky and D. E. Leahy J. Chem. Soc. Perkin Trans II, 1984, 867;
8. A. R. Katritzky, M. De Rosa and N. E. Grzeskowiak J. Chem. Soc. Perkin Trans. II, 1984, 841.
9. D. Rasala, T. Bak, E. Kolehmainen, S. Styrcz and R. Gawinecki J. Phys. Org. Chem., 9, 631 (1996) and ref. there in.
10. Calculated using a MOPAC-6 package and AMI approaches.
11. G. Dykes, S. Boruski, J. Heiermann, J. Koming, K. Opwis, G. Henkel, M. Kocerling J. Organomet. Chem., 2000, 108.
12. The same deshielding was observed also for azulene protons in compound 11 except the proton at C2′ strongly shielded by the magnetic field generated by Ph group at C3.
13. C. Roussel, A. T. Balaban, U. Berg, M. Chinon, R. Gallo, G. Klatte, J. A. Memiaghe, J. Metzger and D. Oniciu, Tetraherdon, 40, 4209 (1982);
14. I. Ghiviriga, E. W. Czerwinski and A. T. Balaban, Croatica Chim. Acta, CCACAA, 77, 391 (2004).
15. +-C bond despite the difficulty to accept that explanation. This observation as well as other structural aspects regarding the above studied series of compounds will be approached in the future.
16. 2CH group in compound 7f(iPr).