Domino reactions of 4,5-dicyanopyridazine with dihydroheterocycles: Synthetic and mechanistic features

Journal of Organic Chemistry

Volumn 68, Issue 8, 2003, Pages 3340-3343

  Giomi, Donatella ^a   Cecchi, Marco ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

DOMINO REACTION;

DERIVATIVES; FURAN RESINS; NITRILE RESINS;

HYDRAZINE;

2,3 DIHYDROFURAN; 3,4 DIHYDRO 2H PYRAN; 4,5 DICYANOPYRIDAZINE; 5,6 DICYANOINDOLE DERIVATIVE; DIHYDROHETEROCYCLIC COMPOUND; FURAN DERIVATIVE; HETEROCYCLIC COMPOUND; INDOLE DERIVATIVE; NITRILE; PHTHALONITRILE; PYRAN DERIVATIVE; PYRIDAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BINDING; CHEMICAL REACTION KINETICS; COMPLEX FORMATION; DOMINO REACTION; MOLECULAR MECHANICS; PRODUCT RECOVERY; REACTION ANALYSIS; SPECIES IDENTIFICATION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0037453690     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026761x     Document Type: Article

References (19)

1. (a) Boger, D. L.; Weinreb, S. N. Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: New York, 1987; pp 313-316.
2. (b) Boger, D. L.; Patel, M. Prog. Heterocycl. Chem. 1989, 1, 34-35.
3. (c) Coates, W. J. In Comprehensive Heterocyclic Chemistry II; Boulton, A. J., Ed.; Pergamon: Oxford, UK, 1996; Vol. 6, pp 30-32.
4. For similar effects of CN groups on carbo- and aza-dienes, see: (a) Cobb, R. L.; Vives, V. C.; Mahan, J. E. J. Org. Chem. 1978, 43, 931-936. (b) Sisti, N. J.; Motorina, I. A.; Tran Huu Dau, M.-E.; Riche, C.; Fowler, F. W.; Grierson, D. S. J. Org. Chem. 1996, 61, 3715-3728.
5. For similar effects of CN groups on carbo- and aza-dienes, see: (a) Cobb, R. L.; Vives, V. C.; Mahan, J. E. J. Org. Chem. 1978, 43, 931-936. (b) Sisti, N. J.; Motorina, I. A.; Tran Huu Dau, M.-E.; Riche, C.; Fowler, F. W.; Grierson, D. S. J. Org. Chem. 1996, 61, 3715-3728.
6. (a) Nesi, R.; Giomi, D.; Turchi, S.; Paoli, P. Tetrahedron 1994, 50, 9189-9194.
7. (b) Giomi, D.; Nesi, R.; Turchi, S.; Coppini, R. J. Org. Chem. 1996, 61, 6028-6030.
8. (c) Giomi, D.; Nesi, R.; Turchi, S.; Mura, E. J. Org. Chem. 2000, 65, 360-364.
9. Turchi, S.; Giomi, D.; Capaccioli, C.; Nesi, R. Tetrahedron 1997, 53, 11711-11720.
10. (a) Turchi, S.; Nesi, R.; Giomi, D. Tetrahedron 1998, 54, 1809-1816.
11. (b) Nesi, R.; Turchi, S.; Giomi, D.; Corsi, C. Tetrahedron 1998, 54, 10851-10856.
12. The stereochemistry is portrayed arbitrarily.
13. For a proper definition and classification of domino reactions, see: Tietze, L. F. Chem. Rev. 1996, 96, 115-136.
14. Nesi, R.; Giomi, D.; Turchi, S.; Falai, A. J. Chem. Soc., Chem. Commun. 1995, 2201-2002.
15. General experimental information was given in: Giomi, D.; Turchi, S.; Danesi, A.; Faggi, C. Tetrahedron 2001, 57, 4237-4242.
16. The values in square brackets refer to the minor component.
17. (a) Gompper, R.; Elser, W. Liebigs Ann. Chem. 1969, 725, 64-72.
18. (b) Gompper, R.; Elser, W. Org. Synth. 1968, 48, 97-101.
19. Duflos, J.; Dupas, G.; Quéguiner, G. J. Heterocycl. Chem. 1983, 20, 1191-1193.