Dienophilicity of imidazole in inverse electron demand Diels-Alder reactions; intramolecular reactions with 1,2,4-triazines

Tetrahedron Letters

Volumn 38, Issue 43, 1997, Pages 7499-7502

  Neipp, Christopher E ^a   Ranslow, Peter B ^a   Wan, Zhaokui ^a   Snyder, John K ^a  

^a Boston University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,4 TRIAZINE DERIVATIVE; IMIDAZO[4,5 C]PYRIDINE DERIVATIVE; NAPHTHYRIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030791731     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01800-5     Document Type: Article

References (23)

1. Wan Z.-K., Snyder J.K. Tetrahedron Lett. 38:1997;7495-7498.
2. For a review of intramolecular inverse electron demand Diels-Alder reactions: Taylor, E.C. Bull. Soc. Chim. Belg. 1988, 97, 599 - 613. For reviews of inverse electron demand Diels-Alder reactions, see ref. 1 of preceding communication.
3. See ref. , preceding communication.
4. Benson S.C., Li J.-H., Snyder J.K. J. Org. Chem. 57:1992;5285-5287.
5. Li J.-H., Snyder J.K. J. Org. Chem. 58:1993;516-519.
6. Original procedure adapted from: Reppe, W. Liebigs Ann. Chem. 1955, 596, 1 (actual procedure on p. 215).
7. Boger, D.L.; Weinreb, S.M. In Hetero Diels-Alder Methodology in Organic Synthesis; Wasserman, H.H., Ed.; Organic Chemistry Monograph 47; Academic: New York, 1987; Chapter 10.
8. Procedure adapted from: Bartlett, M.F.; Taylor, W.I. J. Am. Chem. Soc. 1960, 82, 5941 - 5846.
9. Procedure adapted from: (a) Snyder, H.R.; Hansch, C.H.; Katz, L.; Parmerter, S.M.; Spaeth, E.C. J. Am. Chem. Soc. 1948, 70, 219 - 221.
10. (b) Cain, M.; Mantei, R.; Cook, J.M. J. Org. Chem. 1982, 47, 4933 - 4936.
11. (c) Still, I.W.J.; McNulty, J. Heterocycles 1989, 29, 2057 - 2059.
12. In past work we have been unable to intercept analogous dihydropyridine intermediates produced from the cycloadditions between 1,2,4-triazines and indole with Pd-C, so this was not attempted here: Benson, S.C.; Gross, J.L.; Snyder, J.K. J. Org. Chem. 1990, 55, 3257 - 3269.
13. Barlin G.B., Ireland S.J., Nguyen T.M.T., Kotecka B., Reickmann K.H. Aust. J. Chem. 47:1994;1143-1154. and references therein.
14. (a) Allott, C.P.; Bradbury, R.H.; Dennis, M.; Fisher, E.; Luke, R.W.A.; Major, J.S.; Oldman, A.A.; Pearce, R.J.; Reid, A.C.; Roberts, D.A.; Rudge, D.A.; Russell, S.T. Bioorg. Med. Chem. Lett. 1993, 3, 899 - 904.
15. (b) Norman, M.H.; Smith, H.D.; Andrews, C.W.; Tang, F.L.M.; Cowan, C.L.; Steffen, R.P. J. Med. Chem. 1995, 38, 4670 - 4678.
16. (a) Rapoport, H.; Batcho, A.D. J. Org. Chem. 1963, 28, 1753 - 1759, and earlier references cited therein.
17. (b) Hamada, Y.; Takeuchi, I. Chem. Pharm. Bull. 1970, 19, 1857 - 1862.
18. (c) Gogte, V.N.; Kelkar, S.V.; Tilak, B.D. Indian J. Chem. 1980, 19B, 1011 - 1013.
19. For more recent examples: (d) Chen, J.I.; Steglich, W. J. Heterocycl. Chem. 1993, 30, 909 - 912.
20. (e) Soufyane, M.; Mirand, C.; Levy, J. Tetrahedron Lett. 1993, 34, 7737 - 7740. Also, see reference 11.
21. Reviews: (a) Paudler, W.W.; Kress, T.J. Adv. Heterocycl. Chem. 1970, 11, 123 - 175.
22. (b) Paudler, W.W.; Sheets; R.M. Adv. Heterocycl. Chem. 1983, 33, 147 - 184.
23. Wan, J.-K.; Snyder, J.K. Manuscript in preparation; to be submitted to Tetrahedron Lett. 1997.