Intramolecular Diels-Alder Reaction of 2-Cyano-1-aza-1,3-butadienes

Journal of Organic Chemistry

Volumn 62, Issue 7, 1997, Pages 2093-2097

  Sisti, Nicholas J ^c   Zeller, Emmanuel ^c   Grierson, David S ^b   Fowler, Frank W ^a  

^a STONY BROOK UNIVERSITY   (United States)

^b CNRS   (France)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0345890132     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961403d     Document Type: Article

References (45)

1. (a) Michel, J. P. Nat. Prod. Rep. 1994, 11, 17.
2. (b) Howard, A. S.; Michael, J. P. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1986; Vol. 28, p 183.
3. 4
4. (a) Elbein, A. D.; Molyneux, R. J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Springer Verlag: New York, 1986; Vol. 4, p 1.
5. (b) Fleet, G. W. J.; Fellows, L. E.; Winchester, B. Bioactive Compounds from Plants; Ciba Foundation Symposium 154; Wiley: Chichester, 1990; p 112.
6. Daly, J. W.; Spande, T. F. In Alkaloids: Chemical and Biological Perspectives, Pelletier, S., W., Ed.; Springer Verlag: New York, 1987; Vol. 5, p 1.
7. Weinreb and co-workers have applied the intramolecular Diels-Alder reaction of N-acyl imines to the preparation of piperidine, indolizidine, and quinolizidine alkaloids. For some examples, see Chapter 2 in ref 6.
8. Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, 1987.
9. For some selective reviews on the intramolecular Diels-Alder reaction, see: (a) Roush, W. R. In Comprehensive Organic Synthesis; Paquette, L. A., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 513. (b) Craig, D. J. Chem. Soc. Rev. 1987, 16, 187. (c) Fallis, A. G. Can. J. Chem. 1984, 62, 183. (d) Ciganek, E. Org. React. 1984, 32, 1.
10. For some selective reviews on the intramolecular Diels-Alder reaction, see: (a) Roush, W. R. In Comprehensive Organic Synthesis; Paquette, L. A., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 513. (b) Craig, D. J. Chem. Soc. Rev. 1987, 16, 187. (c) Fallis, A. G. Can. J. Chem. 1984, 62, 183. (d) Ciganek, E. Org. React. 1984, 32, 1.
11. For some selective reviews on the intramolecular Diels-Alder reaction, see: (a) Roush, W. R. In Comprehensive Organic Synthesis; Paquette, L. A., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 513. (b) Craig, D. J. Chem. Soc. Rev. 1987, 16, 187. (c) Fallis, A. G. Can. J. Chem. 1984, 62, 183. (d) Ciganek, E. Org. React. 1984, 32, 1.
12. For some selective reviews on the intramolecular Diels-Alder reaction, see: (a) Roush, W. R. In Comprehensive Organic Synthesis; Paquette, L. A., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 513. (b) Craig, D. J. Chem. Soc. Rev. 1987, 16, 187. (c) Fallis, A. G. Can. J. Chem. 1984, 62, 183. (d) Ciganek, E. Org. React. 1984, 32, 1.
13. For an efficient method for the preparation of the quinolizidine alkaloid deoxynupharidine using the intramolecular Diels-Alder reaction of an N-acyl-1-azadiene, see: Hwang, Y. C.; Fowler, F. W. J. Org. Chem. 1985, 50, 2719.
14. For successful intramolecular Diels-Alder reactions of 1-azadienes, see: (a) Teng, M.; Fowler, F. W. J. Org. Chem. 1990, 55, 5646 and work cited therein. (b) Jun, M. E.; Choi, Y. M. J. Org. Chem. 1991, 56, 6729. (c) Uyehara, T.; Suzuki, I.; Yamamoto, Y. Tetrahedron Lett. 1990, 31, 3753. (d) Whitesell, M. A.; Kyba, E. P. Tetrahedron Lett. 1984, 25, 2119. (e) See also ref 6, Chapter 9, and ref 10c.
15. For successful intramolecular Diels-Alder reactions of 1-azadienes, see: (a) Teng, M.; Fowler, F. W. J. Org. Chem. 1990, 55, 5646 and work cited therein. (b) Jun, M. E.; Choi, Y. M. J. Org. Chem. 1991, 56, 6729. (c) Uyehara, T.; Suzuki, I.; Yamamoto, Y. Tetrahedron Lett. 1990, 31, 3753. (d) Whitesell, M. A.; Kyba, E. P. Tetrahedron Lett. 1984, 25, 2119. (e) See also ref 6, Chapter 9, and ref 10c.
16. For successful intramolecular Diels-Alder reactions of 1-azadienes, see: (a) Teng, M.; Fowler, F. W. J. Org. Chem. 1990, 55, 5646 and work cited therein. (b) Jun, M. E.; Choi, Y. M. J. Org. Chem. 1991, 56, 6729. (c) Uyehara, T.; Suzuki, I.; Yamamoto, Y. Tetrahedron Lett. 1990, 31, 3753. (d) Whitesell, M. A.; Kyba, E. P. Tetrahedron Lett. 1984, 25, 2119. (e) See also ref 6, Chapter 9, and ref 10c.
17. For successful intramolecular Diels-Alder reactions of 1-azadienes, see: (a) Teng, M.; Fowler, F. W. J. Org. Chem. 1990, 55, 5646 and work cited therein. (b) Jun, M. E.; Choi, Y. M. J. Org. Chem. 1991, 56, 6729. (c) Uyehara, T.; Suzuki, I.; Yamamoto, Y. Tetrahedron Lett. 1990, 31, 3753. (d) Whitesell, M. A.; Kyba, E. P. Tetrahedron Lett. 1984, 25, 2119. (e) See also ref 6, Chapter 9, and ref 10c.
18. For successful intramolecular Diels-Alder reactions of 1-azadienes, see: (a) Teng, M.; Fowler, F. W. J. Org. Chem. 1990, 55, 5646 and work cited therein. (b) Jun, M. E.; Choi, Y. M. J. Org. Chem. 1991, 56, 6729. (c) Uyehara, T.; Suzuki, I.; Yamamoto, Y. Tetrahedron Lett. 1990, 31, 3753. (d) Whitesell, M. A.; Kyba, E. P. Tetrahedron Lett. 1984, 25, 2119. (e) See also ref 6, Chapter 9, and ref 10c.
19. Other nitrogen substituents, such as N,N-dimethylamino and sulfonyl groups are known to activate azadienes with respect to the Diels-Alder reaction but are not directly produce indolizidines and quinolizidines. (a) See ref 6, Chapter 9. (b) Ghosez, L. J. Heterocycl. Chem. 1985, 22 (Suppl. Issue Lect. Heterocycl. Chem. 8), 69. (e) Boger, D. L.; Corbett, W. L. J. Org. Chem. 1993, 58, 2068 and work cited therein.
20. Other nitrogen substituents, such as N,N-dimethylamino and sulfonyl groups are known to activate azadienes with respect to the Diels-Alder reaction but are not directly produce indolizidines and quinolizidines. (a) See ref 6, Chapter 9. (b) Ghosez, L. J. Heterocycl. Chem. 1985, 22 (Suppl. Issue Lect. Heterocycl. Chem. 8), 69. (e) Boger, D. L.; Corbett, W. L. J. Org. Chem. 1993, 58, 2068 and work cited therein.
21. Other nitrogen substituents, such as N,N-dimethylamino and sulfonyl groups are known to activate azadienes with respect to the Diels-Alder reaction but are not directly produce indolizidines and quinolizidines. (a) See ref 6, Chapter 9. (b) Ghosez, L. J. Heterocycl. Chem. 1985, 22 (Suppl. Issue Lect. Heterocycl. Chem. 8), 69. (e) Boger, D. L.; Corbett, W. L. J. Org. Chem. 1993, 58, 2068 and work cited therein.
22. (a) Sisti, N. J.; Fowler, F. W.; Grierson, D. S. Synlett 1991, 816.
23. (b) For a comparison of nitrogen activating substituents, see: Trione, C.; Toledo, L. M.; Kuduk, S. D.; Fowler, F. W.; Grierson, D. S. J. Org. Chem. 1993, 58, 2075.
24. (c) Sisti, N. J.; Motorina, I. A.; Tran Huu Dau, M.-E.; Riche, C.; Fowler, F. W.; Grierson, D. J. Org. Chem. 1996, 61, 3715.
25. (a) Grierson, D. S.; Harris, M.; Husson, H.-P. J. Am. Chem. Soc. 1980, 102, 1064.
26. (b) Albright, J. D. Tetrahedron 1983, 39, 3207.
27. (c) Shafran, Y. M.; Bakulev, B. A.; Mokrushin, V. S. Russ. Chem. Rev. 1989, 58, 148.
28. (d) Viehe, H. G.; Merenyi, R.; Stella, L.; Janousek, Z. Angew. Chem., Ind. Ed. Engl. 1979, 18, 917.
29. (e) Zeller, E.; Sajus, H.; Grierson, D. Synlett 1991, 44.
30. (f) Yue, C.; Royer, J.; Husson, H.-P. J. Org. Chem. 1992, 57, 4211.
31. Albrecht, H.; Vonderheid, C. Synthesis 1975, 512.
32. House, H. O.; Lee, L. F. J. Org. Chem. 1976, 41, 863.
33. Harding, K. E.; Burks, S. R. J. Org. Chem. 1981, 46, 3920.
34. Lin, Y.-T.; Houk, K. N. Tetrahedron Lett. 1985, 26, 2269. A Diels-Alder adduct was obtained in 85% yield when the nonatriene was heated for 35 h at 190 °C.
35. These conclusions are supported by MM2 calculations using MacroModel version 4.0 developed by C. Still, Columbia University. These calculations predict that the dihedral angle between the cis and trans C-H bonds of C-2 and C-3 for 4 are 32 and 153°, respectively. These same bonds for 5 are 39 and 91°.
36. In the all carbon intramolecular Diels-Alder reaction the endo reaction pathway leads to the cis-fused product whereas the exo reaction pathway leads to the trans-fused product. Although cis- and irons-fused transition states are also involved in the nitrogen analog of this reaction, nitrogen inversion precludes distinguishing their products.
37. Supporting this assumption, MM2 calculations predict that the conformation of 8 with an axial phenyl substituent at C-7 and an axial hydrogen at C-8a is 2.5 kcal/mol more stable than the conformation of 8 with an equatorial phenyl substituent at C-7 and an equatorial H at C-8a.
38. The nearly identical chemical shift indicates that the bridge-head hydrogen in both isomers is anti to the nitrogen lone pair of electrons (see ref 21a).
39. For references related to the structure and NMR spectroscopy of indolizidines and quinolizidines, see: (a) Crabb, T. A.; Newton, R. P. Chem. Rev. 1971, 71, 109. (b) Tourwe, D.; Binst, G. V. Heterocycles 1978, 9, 507. (c) Skvortsov, I. M. Russ. Chem. Rev. 1979, 48, 262. (d) Crabb, T. A. In Annual Reports in NMR Spectroscopy; Webb, G. A., Ed.; Academic Press: London, 1982; p 60.
40. For references related to the structure and NMR spectroscopy of indolizidines and quinolizidines, see: (a) Crabb, T. A.; Newton, R. P. Chem. Rev. 1971, 71, 109. (b) Tourwe, D.; Binst, G. V. Heterocycles 1978, 9, 507. (c) Skvortsov, I. M. Russ. Chem. Rev. 1979, 48, 262. (d) Crabb, T. A. In Annual Reports in NMR Spectroscopy; Webb, G. A., Ed.; Academic Press: London, 1982; p 60.
41. For references related to the structure and NMR spectroscopy of indolizidines and quinolizidines, see: (a) Crabb, T. A.; Newton, R. P. Chem. Rev. 1971, 71, 109. (b) Tourwe, D.; Binst, G. V. Heterocycles 1978, 9, 507. (c) Skvortsov, I. M. Russ. Chem. Rev. 1979, 48, 262. (d) Crabb, T. A. In Annual Reports in NMR Spectroscopy; Webb, G. A., Ed.; Academic Press: London, 1982; p 60.
42. For references related to the structure and NMR spectroscopy of indolizidines and quinolizidines, see: (a) Crabb, T. A.; Newton, R. P. Chem. Rev. 1971, 71, 109. (b) Tourwe, D.; Binst, G. V. Heterocycles 1978, 9, 507. (c) Skvortsov, I. M. Russ. Chem. Rev. 1979, 48, 262. (d) Crabb, T. A. In Annual Reports in NMR Spectroscopy; Webb, G. A., Ed.; Academic Press: London, 1982; p 60.
43. For example, an analogous N-acyl azadiene requires heating for 6 h at 110 °C, compared to 24 h at the same temperature for azadiene 3.
44. Sustman, R.; Korth, H.-G. Adv. Phys. Org. Chem. 1990, 26, 131.
45. Houk, K. N.; Li, Y.; Evanseck, J. D. Angew. Chem., Int. Ed. Engl. 1992, 31, 682.