Hetero Diels-Alder reactions of 4,5-dicyanopyridazine with alkenes

Tetrahedron

Volumn 53, Issue 34, 1997, Pages 11711-11720

  Turchi, Stefania ^a   Giomi, Donatella ^a   Capaccioli, Caterina ^a   Nesi, Rodolfo ^a  

^a CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; CYANIDE; CYCLOHEXANE DERIVATIVE; DECALIN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS;

BETULACEAE;

EID: 0030762420     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00737-0     Document Type: Article

References (16)

1. (a) Boger, D.L.; Weinreb, S. N. Hetero Diels-Alder Methodology in Organic Synthesis, Academic Press: New York, 1987; pp. 323-357;
2. (b) Neunhoeffer, H. in Comprehensive Heterocyclic Chemistry II; Vol. 6, Boulton, A. J. Ed. Pergamon Press: Oxford, 1996; pp. 533-538;
3. (c) Sauer, J.; ibid.; pp. 913-944.
4. (a) Ref. 1a; pp. 313-316;
5. (b) Boger, D. L.; Patel, M. Progr. Heterocycl. Chem. 1989, 1, 34-35;
6. (c) Coates, W. J. in Comprehensive Heterocyclic Chemistry II; Vol. 6, Boulton, A. J. Ed. Pergamon Press: Oxford, 1996; pp. 30-32.
7. Nesi, R.; Giomi, D.; Turchi, S.; Paoli, P. Tetrahedron 1994, 50, 9189-9194.
8. Nesi, R.; Giomi, D.; Turchi, S.; Falai, A. J. Chem. Soc., Chem. Commun. 1995, 2201-2202.
9. Under these conditions, oxidation of 4 into 5 was favoured with respect to further cycloadditions with 2.
10. The stereochemistry of 3 is portrayed arbitrarily.
11. Weidner, C. H.; Michaels, F. M.; Beltman, D. J.; Montgomery, C. J.; Wadsworth, D. H.; Briggs, B. T.; Picone, M. L. J. Org. Chem. 1991, 56, 5594-5598.
12. Only compound 5 has been reported previously; e.g., see Thoma, P.; Habermann, W.; Kranz, J. Ger. Offen. 2,711,005/1978 (Chem. Abstr. 1979, 90, 7594).
13. Apart from a few overlaps, almost identical intensities were observed for the corresponding resonances of the two structures.
14. 4J coupling with the exo H-6 proton.
15. Di Stefano, L.; Castle, R. N. J. Heterocycl. Chem. 1968, 5, 53-59.
16. The values in square brackets refer to the most evident resonances of the minor component, that were exploited for a tentative evaluation of the relative amounts of the two isomers.