Diels-alder cycloadducts of [60]fullerene with pyrimidine o-quinodimethanes

Journal of Organic Chemistry

Volumn 63, Issue 20, 1998, Pages 6809-6813

  Gonzalez, Beatriz ^a   Herrera, Antonio ^a   Beat, ^a   Martm, Nazario ^a   Martímez, Roberto ^a   Florencio Moreno, Luis Sânchez ^a   Sánchez, Angel ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33646801255     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980189l     Document Type: Article

References (42)

1. Khan, S. L; Oliver, A. M.; Paddon-Row: M. N.; Rubin, Y. J. Am. Chem. Soc. 1993, 115, 4919.
2. Belik, P.; Gügel, A.; Spickermann, J.; Müllen, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 78.
3. Diederich, F.; Jonas, H.; Grämlich, V.; Hermann, A.; Ringsdorf, H.; Thilgen, C. Helv. Chim. Acta 1993, 76, 2445.
4. Prato, M.; Suzuki, T.; Foroudian, H.; Li, Q.; Khemani, K.; Wudl, F.; Leonetti, J.; Little, R. D.; White, T.; Rickborn, B.; Yamago, S.; Nakamura, E. J. Am. Chem. Soc. 1993,115, 1594.
5. Wilson, S. R.; Kaprinidis, N.; Wu, Y.; Schuster, D. J. Am. Chem. Soc. 1993, 115, 8495.
6. For a review see: Hirsch, A. Synthesis 1995, 895.
7. For a review on o-quinodimethanes, see: Martin, N.; Seoane, C.; Hanack, M. Org. Prep. Proced. Int. 1991, 23, 237.
8. Ando, K.; Takayama, H. Heterocydes 1994, 37, 1417.
9. Chou, T.-S. Rev. Heteroat. Chem. 1993, 8, 65.
10. Chou, T.-S.; Chang, R.-C. J. Org. Chem. 1993, 58, 493.
11. Chaloner, M. L.; Crew, A. P. A.; O'Neill, P. M.; Storr, R. C.; Yelland, M. Tetrahedron 1992, 48, 8101.
12. Sijbesma, R. P.; Srdanov, G.; Wudl, F.; Castoro, J. C.; Wilkins, Ch.; Friedman, S. H.; DeCamp, D. L.; Kenyon, G. L. J. Am. Chem. Soc. 1993, 115, 6510.
13. Friedman, S. H.; DeCamp, D. L.; Sijbesma, R. P.; Srdanov, G.; Wudl, F.; Kenyon, G. L. J. Am. Chem. Soc. 1993,115, 6506.
14. Tokuyama, H.; Yamago, S.; Nakamura, E. J. Am. Chem. Soc. 1993, 115, 7918.
15. Toniolo, C.; Bianco, A.; Maggini, M.; Scorrano, G.; Prato, M.; Marastoni, M.; Tomatis, R.; Spisani, S.; Palù, G.; Blair, E. D. J. Med. Chem. 1994, 37, 4558.
16. da Ros, T.; Prato, M.; Novello, F.; Maggini, M.; Banfi, E. J. Org. Chem. 1996, 61,9070.
17. Zan, Y.-Z.; Chen, C.-H.; Anderson, J. L.; Sigman, D. S.; Foote, C. S.; Rubin, Y. Tetrahedron 1996, 52, 5179.
18. For a recent review, see: Jensen, A. W.; Wilson, S. R.; Schuster, D. L. Bioorg. Med. Chem. 1996, 4, 767.
19. Prato, M. J. Mater. Chem. 1997, 7, 1097.
20. For a recent review on the synthesis of heterocycle-containing [60]fullerenes, see: Eguchi, S.; Ohno, M.; Kojima, S.; Koide, N.; Yashiro, A.; Shirakawa, Y.; Ishida, H. Fullerene Sei. Technol. 1996,4, 303.
21. Fernândez-Paniagua, U. M.; Illescas, B. M.; Martin, N.; Seoane, C. J. Chem. Soc., Perkin Trans, l 1996, 1077.
22. (a) Fernândez-Paniagua, U. M.; Illescas, B. M.; Martin, N.; Seoane, C.; de la Cruz, P.; de la Hoz, A.; Langa, F. J. Org. Chem. 1997, 62, 3705. An alternative synthetic procedure was simultaneously reported from 2-hydroxycyclohexanone-fused [60]fullerene. See:
23. (b) Torres-Garcia G.; Luftmann, H.; Wolff, Ch.; Mattay, J. J. Org. Chem. 1997, 62, 2752.
24. Ohno, M.; Koide, N.; Sato, H.; Eguchi, S. Tetrahedron 1997, 53, 9075.
25. (a) Tome, A. C.; Cavaleiro, J. A. S.; Storr, R. C. Tetrahedron 1996, 52,1735.
26. (b) Tome, A. C.; Cavaleiro, J. A. S.; Storr, R. C., Tetrahedron 1996, 52, 1723.
27. Herrera, A.; Martfnez, R.; Gonzalez, B.; Illescas, B.; Martin, N.; Seoane, C. Tetrahedron Lett. 1997, 38, 4873.
28. Garcia Martînez, A.; Herrera Fernândez, A.; Moreno Jiménez, F.; Garcia Fraile, A.; Subramanian, L. R.; Hanack, M. J. Org. Chem. 1992, 57, 1627.
29. Schlosser, M. Houben-Weyl "Methoden der Organishen Chemie"', Georg Thieme: Stuttgart, 1972; Vol V/lb, p 201.
30. Tome, A. C.; Enes, R. F.; Cavaleiro, J. A. S.; Elguero, J. Tetrahedron Lett. 1997, 38, 2557.
31. (a) Isaacs, L.; Wehrsig, A.; Diederich, F. Helv. Chim. Acta 1993, 76, 1231.
32. (b) Rubin, Y.; Khan, S.; Freedberg, D. I.; Yeretzian, C. J. Am. Chem. Soc. 1993, 115, 344.
33. (a) Zhang, X.; Foote, C. S. J. Org. Chem. 1994, 59, 5235.
34. (b) Tago, T.; Minowa, T.; Okada, Y.; Nishimura, J. Tetrahedron Lett. 1993, 34, 8461.
35. Nakamura, Y.; Minowa, T.; Shizuka, H.; Nishima, J. J. Chem. Soc., Perkin Trans. 2 1995, 2351.
36. Illescas, B. M.; Martin, N.; Seoane, C.; Ortf, E.; Viruela, P. M.; Viruela, R.; de la Hoz, A. J. Org. Chem. 1997, 62, 7585.
37. Sandström, J. Dynamic NMR Spectroscopy; Academic Press: London, 1982; p 96.
38. Stewart, J. J. P. J. Comput. Chem. 1989, 10, 209; 1989, 10, 221. The calculations were carried out using the Hyperchem 3.0 program.
39. lyoda, M.; Sasaki, S.; Sultana, F.; Yoshida, M.; Kuwatani, Y.; Nagase, S. Tetrahedron Lett. 1996, 37, 7987.
40. (a) Chlistunoff, J.; Cliffel, D.; Bard, A. J. Handbook of Organic Conductive Molecules and Polymers; Nalwa, H. S., Ed., John Wiley & Sons Ltd.: New York, 1997; Ch. 7, Vol. 1.
41. (b) Suzuki, T.; Maruyama, Y.; Akasaba, T.; Ando, W.; Kobayashi, K.; Nagase, S. J. Am. Chem. Soc. 1994, 116, 1359.
42. Illescas, B.; Martin, N.; Seoane, C.; de la Cruz, P.; Langa, F.; Wudl, F. Tetrahedron Leu. 1995, 36, 8307.