Synthesis of 7-azabicyclo[2.2.1]heptane and 2-oxa-4-azabicyclo[3.3.1]non-3- ene derivatives by base-promoted heterocyclization of alkyl N-(cis(trans)-3, trans(cis)-4-dibromocyclohex-1-yl)carbamates and N-(cis(trans)-3,trans(cis)-4- dibromocyclohex-1-yl)-2,2,2-trifluoroacetamides

Journal of Organic Chemistry

Volumn 72, Issue 23, 2007, Pages 8656-8670

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

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

^b INSTITUTO DE INVESTIGACIONES BIOMÉDICAS ALBERTO SOLS   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIZATION; NITROGEN PROTECTING GROUP; OXYGEN ATOM; SODIUM HYDRIDES;

AMIDES; DERIVATIVES; NITROGEN; OXYGEN; SODIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

HEPTANE;

2 OXA 4 AZABICYCLO[3.3.1]NON 3 ENE DERIVATIVE; 3 (BENZYLOXY) 8 BROMO 2 OXA 4 AZABICYCLO[3.3.1]NON 3 ENE; 6 (BENZYLOXYCARBONYLAMINO)CYCLOHEX 2 ENYL ACETATE; 7 AZABICYCLO[2.2.1]HEPTANE; ACETAMIDE DERIVATIVE; BENZOXAZOLONE; BICYCLO COMPOUND; CARBAMIC ACID DERIVATIVE; CYCLOHEXENE DERIVATIVE; EPIBATIDINE; HEPTANE DERIVATIVE; N (3,4 DIBROMOCYCLOHEX 1 YL) 2,2,2 TRIFLUOROACETAMIDE DERIVATIVE; N (3,4 DIBROMOCYCLOHEX 1 YL)CARBAMIC ACID DERIVATIVE; OXAZOLONE; UNCLASSIFIED DRUG;

ARTICLE; BINDING COMPETITION; CHEMICAL REACTION KINETICS; CIS TRANS ISOMERISM; CYCLIZATION; DENSITY FUNCTIONAL THEORY; ELIMINATION REACTION; FROG; HETEROCYCLIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ROOM TEMPERATURE; SYNTHESIS; THERMODYNAMICS;

ACETAMIDES; AZABICYCLO COMPOUNDS; BICYCLO COMPOUNDS, HETEROCYCLIC; CARBAMATES; CYCLIZATION; MODELS, CHEMICAL; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 35948992185     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701625a     Document Type: Article

References (74)

1. For some selected reviews on the chemistry and biology of epibatidine and analogues, see: (a) Carroll, F. I. Bioorg. Med. Chem Lett. 2004, 14, 1889.
2. (b) Daly, J. W. J. Med. Chem. 2003, 46, 445.
3. (c) Romanelli, M. N.; Gualteri, F. Med. Res. Rev. 2003, 23, 393.
4. (d) Broka, C. A. Med. Chem. Res. 1994, 4, 449.
5. Spande, T. F.; Garraffo, H. M.; Edwards, M. W.; Yeh, H. J. C.; Pannell, L.; Daly, J. W. J. Am. Chem. Soc. 1992, 114, 3475.
6. Holladay, M. W.; Dart, M. J.; Lynch, J. K. J. Med. Chem. 1997, 40, 4169.
7. Chen, Z.; Trudell, M. L. Chem. Rev. 1996, 96, 1179.
8. (a) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Tetrahedron 1997, 53, 17177.
9. (b) Trost, B. M.; Cook, G. R. Tetrahedron Lett. 1996, 37, 7485.
10. (c) Sirisoma, N. S.; Johnson, C. R. Tetrahedron Lett. 1998, 39, 2059.
11. (d) Szantay, C.; Kardos-Balogh, Z.; Moldvai, I.; Szantay, J.; Temesvari-Major, C. E.; Blasko, G. Tetrahedron 1996, 52, 11053.
12. (e) Ko, S. Y.; Lerpiniere, J.; Linney, I. D.; Wrigglesworth, R. J. Chem. Soc., Chem. Commun. 1994, 1775.
13. (f) Barros, M. T.; Maycock, C. D.; Ventura, M. R. Tetrahedron Lett. 1999, 40, 557.
14. (g) Aggarwal, V. K.; Olofsson, B. Angew. Chem., Int. Ed. 2005, 44, 5516.
15. (h) Kosugi, H.; Abe, M.; Hatsuda, R.; Uda, H.; Kato, M. Chem. Commun. 1997, 1857.
16. (i) Nakashima, H.; Hiroya, K.; Taniguchi, T.; Ogasawara, K. Synlett 1999, 1405.
17. (j) Habermann, J.; Ley, S. V.; Scott, J. S. J. Chem. Soc., Perkin Trans. I 1999, 1253.
18. (a) Evans, D. A.; Scheidt, K. A.; Downey, C. W. Org. Lett. 2001, 3, 3009.
19. (b) Lee, C.-L. K.; Loh, T.-P. Org. Lett. 2005, 7, 2965.
20. (c) Aoyagi, S.; Tanaka, R.; Naruse, M.; Kibayashi, C. J. Org. Chem. 1998, 63, 8397.
21. (a) Fletcher, S. R.; Baker, R.; Chambers, M. S.; Herbert, R. H.; Hobbs, S. C.; Thomas, S. R.; Verrier, H. M.; Watt, A. P.; Ball, R. G. J. Org. Chem. 1994, 59, 1771.
22. (b) Pfister, J. R.; Wymann, W. E.; Weissberg, R. M.; Strosberg, A. M. J. Pharm. Sci. 1985, 74, 208.
23. (c) Ramanaiah, K. C. V.; Zhu, N.; Klein-Stevens, C.; Trudell, M. L. Org. Lett. 1999, 1, 1439.
24. (a) Olivo, H. F.; Hemenway, M. S. J. Org. Chem. 1999, 64, 8968.
25. (b) Avenoza, A.; Busto, J. H.; Cativiela, C.; Peregrina, J. M. Tetrahedron Lett. 1995, 36, 7123.
26. (c) Avenoza, A.; Busto, J. H.; Cativiela, C.; Peregrina, J. M. Synthesis 1998, 1335.
27. (d) Avenoza, A.; Cativiela, C.; Busto, J. H.; Fernández-Recio, M. A.; Peregrina, J. M. Tetrahedron 2001, 57, 545.
28. (a) Palmgren, A.; Larsson, A. L. E.; Bäckwall, J.-E. J. Org. Chem. 1999, 64, 836.
29. (b) Cabanal-Duvillard, I.; Berrein, J.-F.; Royer, J.; Husson, H.-P. Tetrahedron Lett. 1998, 39, 5181.
30. Tachihara, T.; Watanabe, H.; Kitahara, T. Heterocycles 2002, 57, 781.
31. (a) Gómez-Sánchez, E.; Marco-Contelles, J. Tetrahedron 2005, 61, 1207.
32. (b) Gómez-Sánchez, E.; Marco-Contelles, J. J. Heterocycl. Chem. 2006, 43, 1455.
33. (c) Gómez-Sánchez, E.; Marco-Contelles, J. Lett. Org. Chem. 2006, 3, 827.
34. Kapferer, P.; Vasella, A. Helv. Chim. Acta 2004, 87, 2764.
35. (a) Che, C.; Petit, G.; Kotzyba-Hibert, F.; Bertrand, S.; Bertrand, D.; Grutter, T.; Goeldner, M. Bioorg. Med. Chem. Lett. 2003, 13, 1001.
36. (b) Wei, Z.-L.; Petukhov, P. A.; Xiao, Y.; Tückmantel, W.; George, C.; Kellar, K. J.; Kozikowski, A. P. J. Med. Chem. 2003, 46, 921.
37. (c) Carroll, F. I.; Lee, J. R.; Navarro, H. A.; Ma, W.; Brieaddy, L. E.; Abraham, P.; Damaj, M. I.; Martin, B. R. J. Med. Chem. 2002, 45, 4755.
38. Dolci, L.; Dolle, F.; Valette, H.; Vaufrey, F.; Fuseau, C.; Bottlaender, M.; Crouzel, C. Bioorg. Med. Chem. 1999, 7, 467.
39. Corey, E. J.; Loh, T.-P.; AchyuthaRao, S.; Daley, D. C.; Sarshar S. J. Org. Chem. 1993, 58, 5600.
40. (a) Knapp, S.; Kukkola, P. J.; Sharma, S.; Dhar, T. G. M.; Naughton, A. B. J. J. Org. Chem. 1990, 55, 5700.
41. (c) Bayer, A.; Hansen, L. K.; Gautun, O. R. Tetrahedron: Asymmetry 2002, 13, 2407.
42. (d) Compound 22 has also been described as a key intermediate for the synthesis of epibatidine: Cabanal-Duvillard, I.; Berrien, J.-F.; Ghosez, L.; Husson H.-P.; Royer, J. Tetrahedron 2000, 56, 3763.
43. (a) Kimura, M.; Kure, S.; Yoshida, Z.; Tanaka, S.; Fugami, K.; Tamaru, Y. Tetrahedron Lett. 1990, 31, 4887.
44. (b) Tamara, Y.; Kimura, M.; Tanaka, S.; Kure, S.; Yoshida, Z. Bull. Chem. Soc. Jpn. 1994, 67, 2838.
45. (c) Ritter, S.; Horino, Y.; Lex, J.; Schmalz, H.-G. Synlett 2006, 3309.
46. (a) Seerden, J.-P. G.; Tulp, M. Th. M.; Scheeren, H. W.; Kruse, C. G. Bioorg. Med. Chem. 1998, 6, 2103 and references cited therein.
47. (b) Altenbach, H.-J.; Constant, D.; Martin, H.-D.; Mayer, B.; Müller M.; Vogel, E. Chem. Ber. 1991, 124, 791.
48. In view of the reactivity observed with 3-trans,4-cis-dibromocarbamates 11 and 13, similar analysis was not further investigated in related derivatives 15, 17, 19, and 21.
49. Baginski, M.; Claudi, F.; Giorgioni, G.; Fontenla, J. A.; Rosa, E.; Cardellini, M. Bioorg. Chem. 1996, 24, 358.
50. Maier, M. E.; Lapeva, T. Synlett 1998, 891.
51. Ryan, R. J.; Julia, S. Tetrahedron 1973, 29, 3649.
52. (a) Crossley, M. J.; Davies, S. R.; Hambley, T. W. Aust. J. Chem. 1994, 47, 2221.
53. (b) Orlek, B. S.; Borrett, G. T.; Smith, D. M. J. Chem. Soc., Perkin Trans. 1 1993, 1299.
54. (c) Miyamoto, M.; Aoi, K.; Morimoto, M.; Chujo, Y.; Saegusa, T. Macromolecules 1992, 25, 5878.
55. For the sake of brevity, the theoretical study on related processes (formation of 35 and 38 from 13, and 47 from 43) is shown in the Supporting Information.
56. -] was performed (see Figure 1, Supporting Information), and the results reveal a double-well energy profile and a barrierless pathway for the formation of A1.
57. The gas-phase results for the reactions evaluated are summarized in the Supporting Information.
58. Agami, C.; Couty, F. Tetrahedron 2002, 58, 2701.
59. (a) Suárez-Castillo, O. R.; Montiel-Ortega, L. A.; Meléndez-Rodríguez, M.; Sánchez-Zavala, M. Tetrahedron Lett. 2007, 48, 17.
60. (b) Mohapatra, D. K.; Durugkar, K. A. Arkivoc 2005, xiv, 20.
61. Jung, M. E.; Davidov, P. Org. Lett. 2001, 3, 3025.
62. For some DFT studies of intramolecular retro-ene reactions, see: (a) Jabbari, A.; Sorensen, E. J.; Houk, K. N. Org. Lett. 2006, 8, 3105.
63. (b) Yu, Z. X.; Houk, K. N. J. Am. Chem. Soc. 2003, 125, 13825.
64. (c) Loncharich, R. J.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 6947.
65. Moriarty, R. M.; Chany, C. J., II; Vaid, R. K.; Prakash, O.; Tuladhar, S. M. J. Org. Chem. 1993, 58, 2478.
66. (a) Frisch, M. J. et al. Gaussian98, Revision A.11; Gaussian, Inc., Pittsburgh, PA, 2001.
67. (b) Frisch, M. J. et al. Gaussian03, Revision B.03; Gaussian, Inc., Pittsburgh PA, 2003. (See the Supporting Information.)
68. Adamo, C.; Barone, V. J. Chem. Phys. 1998, 108, 664.
69. Kormos, B. L.; Cramer, C. J. J. Phys. Org. Chem. 2002, 15, 712.
70. (a) Clark, T.; Chandrasekhar, J.; Spitznagel, G. W.; Schleyer, P .v. R. J. Comput. Chem. 1983, 4, 294.
71. (b) Lynch, B. J.; Zhao, Y.; Truhlar, D. G. J. Phys. Chem. A 2003, 107, 1384.
72. (a) Buncel, E.; Menon, B. J. Am. Chem. Soc. 1977, 99, 4457.
73. (b) Buncel, E.; Menon, B. J. Organomet. Chem. 1977, 141, 1.
74. Barone, V.; Cossi, M. J. Phys. Chem. A 1998, 102, 1995.