Intramolecular Diels-Alder reaction of pyrazines with an alkenyl side chain

Tetrahedron Letters

Volumn 37, Issue 45, 1996, Pages 8205-8208

  Chen, Bin ^a   Yang, Chu Yao ^a   Ye, De Yong ^a  

^a FUDAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

PYRAZINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

BETULACEAE;

EID: 0030569268     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01868-0     Document Type: Article

References (26)

1. 1. For recent reviews: (a) Roush, W. R. In Comprehensive Organic Synthesis ; Trost, B. M.; Fleming, I., Ed.; Pergamon: Oxford. 1991; Vol. 5, Chapter 4.4.
2. (b) Carruthers, W. Cycloaddition Reaction in Organic Synthesis ; Tetrahedron Organic Chemistry Series Vol. 8, Pergamon: Oxford. 1990: p140.
3. (c) Roush, W. R. In Advances in Cycloaddition ; Curran, D. P., Ed.; JAI Press: Greenwich, CT. 1990, Vol. 2, p91.
4. (d) Taschner, M. J. In Organic Synthesis: Theory and Application ; Hudlicky, T., Ed.: JAI Press: Greenwich, CT. 1989. Vol. 1, p79.
5. (e) Craig, D. Chem. Soc. Rev., 1987, 16, 187.
6. (f) Boger, D. L.; Weireb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis (Organic Chemistry Monograph series) : Academic Press: New York 1987.
7. 2. (a) de Bie, D. A.; Ostrowicz, A.; Geurtsen, G.; van der Plas, H. C. Tetrahedron 1988, 44, 2977.
8. (b) Biebrzychi, M.; de Bie, D. A.; van der Plas, H. C. Tetrahedron 1989, 45, 6211.
9. (c) Geurtsen, B.; de Bie, D. A.; van der Plas, H. C. Tetrahedron 1989, 45, 6519.
10. (d) Haider, N.; van der Plas, H. C. Tetrahedron 1990, 46, 3641.
11. 3. (a) Taylor, E. C.; Macor, J. E. J. Org. Chem. 1987, 52, 4280.
12. (b) Taylor, E. C.; Macor, J. E. J. Org. Chem. 1991, 56, 1807.
13. (c) Seitz, G.; Dietrich, S. Arch. Pharm. (Weinheim) 1984, 317, 379.
14. (d) ibid. 1985, 318, 1048.
15. (e) Wuonola, M. A.; Smallheer, J. M.; Read, J. M.; Calabrese, J. C. Tetrahedron Lett. 1991, 32, 5481.
16. 4. (a) Klein, B.; Berkowitz, J. J. Am. Chem. Soc. 1959, 81, 5160.
17. (b) Klein, B.; Berkowitz, J.; Hetman, N. E. J. Org. Chem. 1961, 26, 126.
18. 5. Yang, Chu-Yao; Huang, Xin-Ming Fu Dan Xue Bao 1980, 19(4), 390. C.A. 95: 132813p.
19. 5. Yang, Chu-Yao; Huang, Xin-Ming Fu Dan Xue Bao 1980, 19(4), 390. C.A. 95: 132813p.
20. 6. Freedman, H. H.; Dubios, R. A. Tetrahedron Lett. 1975, 3251.
21. 2c.
22. 2O (192.30): C 68.57, H 8.52, N 14.85: Found: C 68.70, H 8.39, N 14.57.
23. 9. Urquhart, G. G.; Gates, Jr., J. W.; Connor, R. Org. Synt. Coll. Vol. III, 1955, 363.
24. 10. Leonard, N. J.; Johnson, C. R. J. Org. Chem. 1962, 27, 282.
25. 11. Taylor E. C.; Macor J. E. J. Org. Chem. 1989, 54, 4984.
26. 2=4.2Hz, 1H).