Synthesis and Chemistry of Substituted 1-Azabicyclo[1.1.0]butanes

Synlett

Volumn 1997, Issue 9, 1997, Pages 1029-1039

  Bartnik, Romuald ^a,c   Marchand, Alan P ^b,d,e,f  

^a UNIVERSITY OF LODZ   (Poland)

^b UNIVERSITY OF NORTH TEXAS   (United States)

^c UNIVERSITÉ DE LYON   (France)

^d CASE WESTERN RESERVE UNIVERSITY   (United States)

^e UNIVERSITY OF CHICAGO   (United States)

^f University of Olklahoma   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0542387374     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1520     Document Type: Article

References (70)

1. Castellucci, N. C.; Kato, M.; Zenda, H.; Masamune, S. J. Chem. Soc., Chem. Commun. 1967, 473.
2. Labows, J. N., Jr.; Swern, D. Tetrahedron Lett. 1971, 4523.
3. Anderson, A. G.; Faberburg, D. R.; Lok, R. J. Heterocyclic Chem. 1974, 11, 431.
4. Bartnik, R.; Gebicki, K. Unpublished results.
5. (a) Hassner, A.; Currie, J. O.; Steinfeld, A. S.; Atkinson, R. F. Angew. Chem., Int. Ed. Eng. 1970, 9, 731.
6. (b) Hassner, A.; Currie, J. O.; Steinfeld, A. S.; Atkinson, R. F. J. Am. Chem. Soc. 1973, 95, 2982.
7. (a) Deyrup, J. A.; Clough, S. C. J. Am. Chem. Soc. 1969, 91, 4590.
8. (b) Deyrup, J. A.; Clough, S. C. J. Org. Chem. 1974, 39, 902.
9. Deyrup, J. A.; Moyer, C. L.; Dreifus, P. C.J. Org. Chem. 1970, 35, 3428.
10. Higgins, R. H.; Faircloth, W. J.; Baughman, R. G.; Eaton, Q. L. J. Org. Chem. 1994, 59, 2172.
11. Gaertner, V. R. Tetrahedron Lett. 1968, 5919.
12. (b) Gaertner, V. R. J. Org. Chem. 1970, 35, 3952.
13. Higgins, R. H.; Cromwell, N. H. J. Am. Chem. Soc. 1973, 95, 120 and references cited therein.
14. Okutani, T.; Masuda, K. Chem. Pharm. Bull. 1974, 22, 1498.
15. (a) Hortmann, A. G.; Robertson, D. A. J. Am. Chem. Soc. 1967, 89, 5974.
16. (b) Hortmann, A. G.; Robertson, D. A. J. Am. Chem. Soc. 1972, 94, 2758.
17. (a) Funke, W. Angew. Chem., Int. Ed. Eng. 1969, 8, 70.
18. (b) Funke, W. Chem. Ber. 1969, 102, 3148.
19. Archibald, T. G.; Gilardi, R.; Baum, K.; George, C. J. J. Org. Chem. 1990, 55, 2920.
20. Bartnik, R.; Cebulska, Z.; Faure, R. J. Chem. Soc., Chem. Commun. 1993, 148.
21. Gassman, P. G.; Greenlee, M. L.; Dixon, D. A.; Richtsmeier, S.; Gougoutas, J. Z. J. Am. Chem. Soc. 1983, 105, 5865.
22. (a) Vogel, E. Angew. Chem. 1960, 72, 4.
23. (b) Randic, M.; Maksic, Z. Theor. Chim. Acta 1965, 3, 59.
24. (c) Weigert, F. J..; Roberts, J. D. J. Am. Chem. Soc. 1967, 89, 5962.
25. Wiberg, K. B. Angew. Chem., Int. Ed. Eng. 1986, 25, 312.
26. Alvernhe, G.; Laurent, A.; Touhami, K.; Bartnik, R.; Mloston, G. J. Fluorine Chem. 1985, 29, 363.
27. (a) Alder, R. W.; Chem. Rev. 1989, 89, 1215.
28. (b) See also: Aue, D. H.; Webb, H. M.; Bowers, M. T. J. Am. Chem. Soc. 1975, 97, 4137.
29. Furlong, J. J. P.; Lewkowicz, E. S.; Nudelman, N. S. J. Chem. Soc., Perkin Trans. 2 1990, 1461.
30. Wiberg, K. B.; Lampman, G. M.; Ciula, R. P.; Connor, D. S.; Schertler, P.; Lavanish, J. Tetrahedron 1965. 21, 2749 and references cited therein.
31. (a) Wiberg, K. B.; Ciula, R. P. J. Am. Chem. Soc. 1959, 81, 5261.
32. (b) Wiberg, K. B.; Ciula, R. P.; J. Am. Chem. Soc. 1963, 85, 4045.
33. (c) Wüthrich, K.; Meiboom, S.; Snyder, L. C. J. Chem. Phys. 1970, 52, 230.
34. (a) Bartnik, R.; Cebulska, Z.; Laurent, A. Tetrahedron Lett. 1983, 24, 4197.
35. (b) Bartnik, R., Cebulska, Z.; Laurent, A.; Orlowska, B. J. Chem. Research (S) 1986, 5.
36. Bartnik, R. Unpublished results.
37. Guillemin, J. C.; Denis, J. M. Tetrahedron 1988, 44, 4431.
38. Marchand, A. P.; Rajagopal, D.; Bott, S. G.; Archibald, T. G. J. Org. Chem. 1994, 59, 1608.
39. Bartnik, R.; Cebulska, Z.; Galindo, A.; Porwanski, S. Unpublished results.
40. Calet, S.; Alper, H. Tetrahedron Lett. 1986, 27, 2739.
41. Mauze, R. Tetrahedron Lett. 1984, 25, 843.
42. Marchand, A. P.; Rajagopal, D.; Bott, S. G.; Archibald, T. G. J. Org. Chem. 1995, 60, 4943.
43. Anderson, A. G.; Lok, R. J. Org. Chem. 1972, 37, 3953.
44. Dave, P. R. J. Org. Chem. 1996, 61, 5453.
45. Bartnik, R.; Laurent, A. Tetrahedron Lett. 1974, 3869.
46. (b) Bartnik, R.; Diab, Y.; Laurent, A. Tetrahedron 1977, 33, 1279.
47. Hortmann, A. G.; Martinelli, J. E. Tetrahedron Lett. 1968, 6205.
48. Kurz, J. L.; Gillard, B. K.; Robertson, D. A.; Hortmann, A. G. J. Am. Chem. Soc. 1970, 92, 5008.
49. Gillard, B. K.; Kurz, J. L. J. Am. Chem. Soc. 1972, 94, 7199.
50. Marchand, A. P.; Sharma, G. V. M.; Rajagopal, D.; Shukla, R.; Mloston, G.; Bartnik, R. J. Heterocyclic Chem. 1996, 33, 837.
51. Bartnik, R.; Lesniak, S.; Mloston, G.; Romanski, J. Polish J. Chem. 1994, 68, 1347.
52. Bartnik, R.; Lesniak, S.; Galindo, A. Polish J. Chem. 1994, 68, 719.
53. Marchand, A. P.; Rajagopal, D.; Bott, S. G.; Archibald, T. G. J. Org. Chem. 1994, 59, 5499.
54. Axenrod, T.; Watnick, C.; Yazdehkasti, H.; Dave, P. R. Tetrahedron Lett. 1993, 34, 6677.
55. Hiskey, M. A.; Coburn, M. D.; Mitchell, M. A.; Benicewicz, B. C. J. Heterocyclic Chem. 1992, 29, 1855;
56. (b) Hiskey, M. H.; Coburn, M. D. U. S. Patent 5,336.784; see: Chem. Abstr. 1994, 121, 300750s.
57. Katritzky, A. R.; Cundy, D. J.; Chen, J. J. Heterocyclic Chem. 1994, 31, 271.
58. Hall, H. K.; Smith, C. D.; Blanchard, E. P.; Cherkovsky, E. P. J. Am. Chem. Soc. 1971, 93, 121.
59. Mock, G. B.; Jones, M. Tetrahedron Lett. 1981, 22, 3819.
60. Moltschanov, A. P.; Kopletov, J. B.; Kostikov, R. R. J. Org. Chem. USSR 1988, 24, 390.
61. (a) Moss, R. A.; Maksimovic, L.; Marchand, A. P.; Ramanaiah, K. C. V. Tetrahedron Lett. 1996, 37, 5849.
62. A referee called attention to the fact that bicyclobutanes fail to undergo axial attack by electrophiles. Thus, it seems unlikely that electrophiles would adopt this trajectory when approaching 1-azabicyclo[1.1.0]butanes; see: (a) Hoz, S. In The Chemistry of the Cyclopropyl Group, Rappoport, Z., Ed.; Wiley: New York, 1987; Chapter 19, pp 1146-1148. (b) Razin, V. V.; Eremenko, M. V. Zh. Org. Khim. 1978, 14, 1475; Chem. Abstr. 1979, 90. 103493a. (c) Mazur, S.; Schroder, A. H.; Weiss, M. C. J. Chem. Soc., Chem. Commun. 1977, 262.
63. A referee called attention to the fact that bicyclobutanes fail to undergo axial attack by electrophiles. Thus, it seems unlikely that electrophiles would adopt this trajectory when approaching 1-azabicyclo[1.1.0]butanes; see: (a) Hoz, S. In The Chemistry of the Cyclopropyl Group, Rappoport, Z., Ed.; Wiley: New York, 1987; Chapter 19, pp 1146-1148. (b) Razin, V. V.; Eremenko, M. V. Zh. Org. Khim. 1978, 14, 1475; Chem. Abstr. 1979, 90. 103493a. (c) Mazur, S.; Schroder, A. H.; Weiss, M. C. J. Chem. Soc., Chem. Commun. 1977, 262.
64. A referee called attention to the fact that bicyclobutanes fail to undergo axial attack by electrophiles. Thus, it seems unlikely that electrophiles would adopt this trajectory when approaching 1-azabicyclo[1.1.0]butanes; see: (a) Hoz, S. In The Chemistry of the Cyclopropyl Group, Rappoport, Z., Ed.; Wiley: New York, 1987; Chapter 19, pp 1146-1148. (b) Razin, V. V.; Eremenko, M. V. Zh. Org. Khim. 1978, 14, 1475; Chem. Abstr. 1979, 90. 103493a. (c) Mazur, S.; Schroder, A. H.; Weiss, M. C. J. Chem. Soc., Chem. Commun. 1977, 262.
65. A referee called attention to the fact that bicyclobutanes fail to undergo axial attack by electrophiles. Thus, it seems unlikely that electrophiles would adopt this trajectory when approaching 1-azabicyclo[1.1.0]butanes; see: (a) Hoz, S. In The Chemistry of the Cyclopropyl Group, Rappoport, Z., Ed.; Wiley: New York, 1987; Chapter 19, pp 1146-1148. (b) Razin, V. V.; Eremenko, M. V. Zh. Org. Khim. 1978, 14, 1475; Chem. Abstr. 1979, 90. 103493a. (c) Mazur, S.; Schroder, A. H.; Weiss, M. C. J. Chem. Soc., Chem. Commun. 1977, 262.
66. Mloston, G.; Galindo, A.; Bartnik, R.; Marchand, A. P.; Rajagopal, D. J. Heterocyclic Chem. 1996, 33, 93.
67. Cal, D. Unpublished results.
68. Galindo, A. Ph. D. Dissertation, University of Lodz, 1990.
69. Hortmann, A. G.; Koo, J. J. Org. Chem. 1971, 39, 3781.
70. Bartnik, R.; Kryczka, B.; Libiszowski, J.; Penczek, S. Manuscript in preparation.