The Diels-Alder reaction of 1-cyclohexenecarbaldehyde N,N-dimethylhydrazone with juglone

Heterocyclic Communications

Volumn 3, Issue 1, 1997, Pages 23-28

  Valderrama, Jaime A ^a   Spate, Magdalena ^a   González, M Florencia ^a  

^a PONTIFICIA UNIVERSIDAD CATÓLICA DE CHILE   (Chile)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001885787     PISSN: 07930283     EISSN: None     Source Type: Journal    
DOI: 10.1515/HC.1997.3.1.23     Document Type: Article

References (25)

1. G. Fendrich, W. Zimmermann, J. Gruner and J. A. L. Auden, Eur. Pat. Appl. Ep 304,400C1C07D221/18), 22 Feb 1989, CH Appl. 87/3, 196, 20 Aug 1987 (Chem. Abstr. 112, 752959, 1990).
2. M. P. Gore, S. J. Gould and D. D. Weller, J. Org. Chem. 56, 2289 (1991).
3. M. P. Gore, S. J. Gould and D. D. Weller, J. Org. Chem. 57, 2774 (1992).
4. J. A. Valderrama, R. Araya-Maturana, M. F. González, R. Tapia, F. Fariña and M. C. Paredes, J. Chem. Soc. Perkin Trans. 1, 555 (1991).
5. J. A. Valderrama, R. Araya-Maturana and F. Zuloaga, J. Chem. Soc. Perkin Trans. 1, 1103 (1993).
6. J. A. Valderrama, C. Pessoa-Mahana and R. Tapia, J. Chem. Soc. Perkin Trans. 1, 3521 (1994).
7. J. A. Valderrama, M. Spate, R. Doña and R. Tapia, Bol. Soc. Chil. Quím. 40, 105 (1995).
8. B. Serckx-Poncin, A-M. Hesbain-Frisque and L. Ghosez, Tetrahedron Lett. 23, 3261 (1982).
9. K.T. Potts, D. Bhattacharjee and E. B. Walsh, J. Chem. Soc., Chem. Commun. 114 (1984).
10. C. Gesto, E. de la Cuesta and C. Avendaño, Tetrahedron, 45, 4477 (1989).
11. K. T. Potts, E. B. Walsh and D. Bhattacharje, J. Org. Chem. 52, 2285 (1987).
12. M. Chigr, H. Fillion and A. Rougny, Tetrahedron Lett. 29, 5913 (1988).
13. J. Cabral and P. Laszlo, Tetrahedron 30, 7237 (1989).
14. H. Lee and W. K. Anderson, Tetrahedron Lett. 31, 4405 (1990).
15. J. A. Valderrama, H. Pessoa-Mahana and R. Tapia, J. Heterocycl. Chem. 29, 1177 (1992).
16. O. Cherkaoui, P. Nebois, H. Fillion, M. Domard and B. Fenet, Tetrahedron 52, 9499 (1996).
17. R. E. Klinck and J. B. Stothers, Can. J. Chem. 44 , 45 (1966).
18. I. Shimizu, I. Minami and J. Tsuji, Tetrahedron Lett. 24, 1797 (1983).
19. G. M. Rubottom, R. Marrero and J. M. Gruber, Tetrahedron 39, 861 (1983).
20. S. A. Makin, R. I. Kruglicova, T. K. Tagirov and B. M. Arshava, Zh. Org. Khim. 19, 101 (1983).
21. R. Carlson and C. Rappe, Acta Chem. Scand. B, 29, 634 (1975) and references cited therein.
22. W. B. Manning, T. P. Kelly and G. M. Muschik, Tetrahedron Lett. 2629 (1980).
23. The HOMO coefficients calculations of N,N-dimethylhydrazone 7 were performed by using the AM1 semiempirical method: N-1 = -0.1962, C-2 = -0.3186, C-3 = 0.2782 and C-4 = 0.3593.
24. For a similar benzylic oxidation of benz[a]anthraquinones under aerobic basic conditions see reference 4.
25. 3), 1.89 (m, 4H, 2- and 3-H), 2.94 (m, 2H, 4-H), 3.41 (m, 2H, 1-H), 7.32 (dd, 1H, J = 1.8, 7.8 Hz, 9-H), 7.69 (t, 1H, J = 7.8 Hz, 10-H), 7.76 (dd, 1H, J = 1.8, 7.8 Hz, 11-H), 8.74 (s, 1H, 5-H), 12.47 (s, 1H, OH). Compound 15b: 1.91 (m, 4H, 2-and 3-H), 2.95 (m, 2H, 4-H), 3.46 (m, 2H, 1-H), 7.46 (dd, 1H, J = 1.2, 7.8 Hz, 9-H), 7.67 (t, 1H, J = 7.8 Hz, 9-H), 7.89 (dd, 1H, J = 1.2, 7.8 Hz), 8.76 (s, 1H, 5-H), 12.60 (s, 1H, OH).