Synthesis of 7-azabicyclo[2.2.1]heptane derivatives by transformation of tropinone

Journal of Heterocyclic Chemistry

Volumn 43, Issue 6, 2006, Pages 1455-1459

  Gómez Sánchez, Elena ^a   Marco Contelles, José ^a  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2,7 DICARBETHOXY 7 AZABICYCLO[2.2.1]HEPTANE; 7 AZABICYCLO[2.2.1]HEPTANE DERIVATIVE; ALCOHOL; BICYCLO[3.2.1]OCTANE DERIVATIVE; BROMINE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; COPPER DERIVATIVE; ETHYL 2,2 DIETHOXY 3 OXO 8 AZABICYCLO[3.2.1]OCTANE 8 CARBOXYLATE; ETHYL 2,4 DIBROMO 3 OXO 8 AZABICYCLO[3.2.1]OCTANE 8 CARBOXYLATE; METHYL CHLORIDE; N CARBETHOXYTROPINONE; NORBORNANE DERIVATIVE; TROPANONE;

ARTICLE; BROMINATION; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRESS; CHEMICAL STRUCTURE; FAVORSKII REARRANGEMENT; SYNTHESIS;

EID: 33845417895     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570430607     Document Type: Article

References (26)

1. J. González, J. I. Koontz, M. Hodges, K. R. Nilsson, L. K. Nelly, W. H. Myers, M. Sabat and W. D. Harman, J. Am. Chem. Soc., 117, 3405 (1995).
2. [2a] Z. Chen and M. L. Trudell, Chem. Rev., 96, 1179 (1996).
3. For other 7-azanorbornanes see e.g.; [b] A. Hernández, M. Marcos and H. Rapoport, J. Org. Chem., 60, 2683 (1995);
4. [c] C. Zhang, C. J. Ballay II and M. L. Trudell, J. Chem. Soc., Perkin Trans. 1, 675 (1999);
5. [d] W. Han, J. C. Pelletier, L. J. Mersinger, C. A. Kettner and C. N. Hodge, Org. Lett., 1, 1875 (1999);
6. [e] B. P. Hart and H. Rapoport, J. Org. Chem., 64, 2050 (1999);
7. [f] A. Avenoza, J. L. Barriobero, J. H. Busto, C. Cativiela and J. M. Peregrina, Tetrahedron: Asymmetry, 13, 625 (2002);
8. [g] A. Avenoza, C. Cativiela, M. A. Fernández-Recio and J. M. Peregrina, Tetrahedron: Asymmetry, 10, 3893 (1999);
9. [h] A. J. Moreno-Vargas, C. Schütz, R. Scopelliti and P. Vogel, J. Org. Chem., 68, 5632 (2003);
10. [i] A. J. Moreno-Vargas and P. Vogel, Tetrahedron Lett., 44, 5069 (2003);
11. [j] A. J. Moreno-Vargas and P. Vogel, Tetrahedron: Asymmetry, 14, 3173 (2003);
12. [k] A. J. Moreno-Vargas, I. Robina, E. Petricci and P. Vogel, J. Org. Chem., 69, 4487 (2004).
13. T. F. Spande, H. M. Garraffo, M. W. Edwards, H. J. C. Yeh, L., Pannell and J. W. Daly, J. Am. Chem. Soc., 114, 347 (1992).
14. [4a] R. Xu, G. Chu, and D. Bai, Tetrahedron Lett., 37, 1463 (1996);
15. [b] D. Bai, R. Xu, G. Chu, and X. Zhu, J. Org. Chem., 61, 4600 (1996).
16. B. Badio, H. M. Garraffo, C. V. Plummer, W. L. Padgett, and J. W. Daly, Eur. J. Pharmacol., 321, 189 (1997).
17. D. Che, T. Wegge, M. T. Stubbs, G. Seitz, H. Meier and C. Methfessel, J. Med. Chem., 44, 47 (2001).
18. G. Pandey, A. K. Sahoo, S. R. Gadre, T. D. Bagul and U. D. Phalgune, J. Org. Chem., 64, 4990 (1999).
19. [8a] B. S., Bhatti and T. J. Clark, PCT Int. Appl. 12,245 (2002), Chem. Abstr., 136, 183718j (2002);
20. [b] D. Yohannes and M. W. Bundesmann, Eur. Pat. Appl. 955,301 (1999), Chem. Abstr., 131, 322534h (1999);
21. [c] D. M. Linn and E. H. F. Wong, PCT Int. Appl. 39,366 (2004), Chem. Abstr., 140, 406737a (2004);
22. [d] T. E. Anjeh, T. L. Fevig, J. P. Lawson, D. P. Walker and D. G. Wishka, PCT Int. Appl. 74,292 (2004); Chem. Abstr., 141, 225724u (2004).
23. [9a] P. Chenier and J. C. Kao, J. Org. Chem., 41, 3730 (1976);
24. [b] J. W. Wilt and R. Rasmussen, J. Org. Chem., 40, 1031 (1975);
25. [c] B. Waegell and C. W. Jefford, Bull. Soc. Chim. Fr., 844 (1964)
26. B. Föhlisch, T. Franz and G. Kreiselmeier, Eur. J. Org. Chem., 4257 (2001).