Nitration in the imidazo[1,2-a]pyrazine series. Experimental and computational results

Journal of Heterocyclic Chemistry

Volumn 34, Issue 3, 1997, Pages 701-707

  Vitse, Olivier ^a   Bonnet, Pierre Antoine ^a   Bompart, Jacques ^a   Viols, Henri ^a   Subra, Guy ^a   Chapat, Jean Pierre ^a   Grassy, Gérard ^b  

^a UNIV MONTPELLIER   (France)

^b CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

IMIDAZO[1,2 A]PYRIDINE DERIVATIVE;

ARTICLE; BROMINATION; CARBON NUCLEAR MAGNETIC RESONANCE; CYCLIZATION; ELECTRON TRANSPORT; METHYLATION; NITRATION; NONHUMAN; PROTON TRANSPORT; ULCER;

EID: 0030740970     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570340301     Document Type: Article

References (38)

1. C. Sablayrolles, G. H. Cros, J. C. Milhavet, L. Rechenq, J. P. Chapat, M. Boucard, J. J. Serrano and J. H. McNeill, J. Med. Chem., 27, 206 (1984).
2. A. Michel, F. Laurent, J. Bompart, K. Hadj-Kaddour, J. P. Chapat, M. Boucard and P. A. Bonnet, Br. J. Pharmacol., 110, 1031 (1993).
3. J. J. Kaminski, J. M. Hilbert, B. N. Pramanik, D. M. Solomon and D. J. Conn, J. Med. Chem, 30, 2031 (1987).
4. P. A. Bonnet, A. Michel, F. Laurent, C. Sablayrolles, E. Rechencq, J. C. Mani, M. Boucard and J. P. Chapat, J. Med. Chem., 35, 3358 (1992).
5. M. Ashton, S. J. Cook, G. Fenton, J. A. Karbon and M. N. Palfreyman, J. Med. Chem., 37, 1696 (1994).
6. A. Michel, F. Laurent, J. P. Chapat, M. Boucard and P. A. Bonnet, Arzneim.-Forsch. Drug Res., 45, 1288 (1995).
7. S. J. Cook, K. Archer, A. Martin, K. H. Buchheit, T. Fozard, A. J. Miller, K. R. Elliott, R. W. Foster and R. C. Small, Br. J. Pharmacol., 114, 143 (1995).
8. T. Pocock and R. C. Small, Br. J. Pharmacol., 117, 209P (1996).
9. F. Laurent, T. Pocock, K. R. Elliott, K. Portet, V. Benezech and O. Vitse, Fundam. Clin. Pharmacol., 10, 65 (1996).
10. J. Cortijo, V. Villagrasa, C. Navarrete, C. Sanz, L. Berto, A. Michel, P. A. Bonnet and E. J. Morcillo, Br. J. Pharmacol., 119, 99 (1996).
11. E. Naline, Y. Y. Cui, A. Michel, P. A. Bonnet, H. Bakdach and C. Advenier, Fundam. Clin. Pharmacol., 10, 368 (1996).
12. J. C. Teulade, P. A. Bonnet, J. N. Rieu, H. Viols, J. P. Chapat, G. Grassy and A. Carpy, J. Chem. Res., 202 (1986).
13. J. Bradac, Z. Furek, D. Janezic, S. Molan, B. Stanovnik, M. Tisler and B. Vercek, J. Org. Chem., 42, 4197 (1977).
14. J. C. Teulade, R. Escale, G. Grassy, J. P. Girard and J. P. Chapat, Bull. Soc. Chim., 9-10, 529 (1978).
15. J. C. Teulade, R. Escale, J. C. Rossi, J. P. Chapat, G. Grassy and M. Payard, Aust. J. Chem., 35, 1761 (1982).
16. C. K. Ingold, Structure and Mechanism in Organic Chemistry, 2nd Ed, Bell, London, 1969.
17. P. B. de la Mare and J. H. Ridd, Aromatic Substitution. Nitration and Halogenation, Butherworths, London, 1959, p 57.
18. R. Taylor, Comprehensive Chemical Kinetics, Elsevier, Amsterdam, 1972, p 10.
19. J. G. Hoggett, R. B. Moodie, J. R. Penton and K. Schofield, Nitration and Aromatic Reactivity, Cambridge University Press, Cambridge, 1971.
20. K. Schofield, Aromatic Nitration, Cambridge University Press, Cambridge, 1980.
21. G. A. Olah, R. Malhotra and S. C. Narang, Nitration. Method and Mechanism, VCH Pubhshers, Inc., New York, 1989, p 117.
22. R. Taylor, Electrophilic Aromatic Substitution John Wiley and Sons Ltd, Chichester, 1990, p 263.
23. A. R. Katritzky and R. Taylor Electrophilic Substitution of Heterocycles: Quantitative Aspects, Advances in Heterocycle Chemistry, 1990, p 39.
24. S. R. Hartshorn, R. B. Moodie and K. Schofield, J. Chem. Soc., (B) 2454 (1971).
25. P. A. Bonnet, C. Sablayrolles and J. P. Chapat, Aust. J. Chem., 37, 1357 (1984).
26. P. Politzer, K. Jayasuriya, P. Sjoberg and P. R. Laurence, J. Am. Chem. Soc., 107, 1174 (1985).
27. J. Feng, X. Zheng and M. C. Zerner, J. Org. Chem., 51, 4531 (1986).
28. A. Herrero, C. Ochoa, M. Stud, F. Florencio, I. Hernandez-Fuentes, C. Abradelo and J. L. G. de Paz, J. Org. Chem., 54, 5025 (1989).
29. K. J. Szabo, A. B. Hörnfeld and S. Gronowitz, J. Org. Chem., 56, 1590 (1991).
30. M. L. Trudell, S. L. Lifer, Y. C. Tan, W. B. England and J. M. Cook, J. Org. Chem., 53, 4185 (1988).
31. Y. Blache, A. Gueiffier, A. Elhakmaoui, H. Viols, J. P. Chapat, O. Chavignon, J. C. Teulade, G. Grassy, G. Dauphin, and A. Carpy, J. Heterocyclic Chem., 32, 1317 (1995).
32. MAD, proquantum and prosimulate softwares. Oxford Molecular Ltd., Magdalen Center, Oxford Science Park, Stanford of Thames, Oxford OX4 4GA, United Kingdom.
33. R. Escale, J. P. Girard, J. C. Rossi, J. C. Teulade and G. Grassy, Eur. J. Med. Chem., 2, 121 (1983).
34. P. Kowalski and J. Korchowiec, J. Mol. Struct. (Theochem), 288, 119 (1993).
35. J. Arriau, O. Chalvet, A. Dargelos, and G. Maury, J. Heterocyclic Chem., 11, 1013 (1974).
36. P. Politzer and K. C. Daiker, The Force Concept in Chemistry, Chapter 7, B. M. Deb, ed, Van Nostrand Reinhold, New York, 1981.
37. P. Politzer and D. G. Truhlar, Chemical Applications of Atomic and Molecular Electrostatic Potentials, Plenum Press, New York, 1981.
38. W. Langenaeker, F. de Proft, and P. Geerlings, J. Phys. Chem., 99, 6424 (1995).