Preparation of hexahydrobenzo[f]isoquinolines using a vinylogous Pictet-Spengler cyclization

Organic Letters

Volumn 2, Issue 23, 2000, Pages 3635-3638

  Cesati III, Richard R ^a   Katzenellenbogen, John A ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKYNE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; ISOQUINOLINE DERIVATIVE; KETONE; RADIOPHARMACEUTICAL AGENT;

ARTICLE; CHEMISTRY; CYCLIZATION; SYNTHESIS;

ALDEHYDES; ALKYNES; CYCLIZATION; INDICATORS AND REAGENTS; ISOQUINOLINES; KETONES; RADIOPHARMACEUTICALS;

EID: 0034676527     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006533u     Document Type: Article

References (42)

1. Pictet, A.; Spengler, T. Ber. Dtsch. Chem. Ges. 1911, 44, 2030.
2. (a) Bailey, P. D.; Morgan, K. M. Chem. Commun. 1996, 1479.
3. (b) Corey, E. J.; Gin, D. Y.; Kania, R. S. J. Am. Chem. Soc. 1996, 118, 9202.
4. (c) Hino, T.; Nakagawa, M. Heterocycles 1997, 46, 673.
5. (a) Dijkink, J.; Speckamp, W. N. Tetrahedron Lett. 1977, 935.
6. (b) Kano, S.; Yuasa, Y. Heterocycles 1983, 20, 857.
7. (c) Schleigh, W. R.; Catala, A.; Popp, F. D. J. Chem. Soc. 1965, 379.
8. (d) Zunnebeld, W. A.; Speckamp, W. N. Tetrahedron 1975, 31, 1717.
9. Douglas, J. L.; Meunier, J. Can. J. Chem. 1975, 53, 3681.
10. (a) Czarnocke, A.; Arazby, Z. Heterocycles 1999, 44, 2871.
11. (b) Rozwadowska, M. D. Heterocycles 1994, 39, 903.
12. (a) Cox, E. D.; Cook, J. M. Chem. Rev. 1995, 95, 1797.
13. (b) Soe, T.; Kawate, T.; Fukui, N.; Hino, T.; Nakagawa, M. Heterocycles 1996, 50, 1033.
14. (c) Waldmann, H.; Schmidt, G. Tetrahedron 1994, 50, 11865.
15. (a) Cox, E. D.; Hamaker, L. K.; Li, J.; Yu, P.; Czerwinski, K. M.; Deng, L.; Bennet, D. W.; Cook, J. M. J. Org. Chem. 1997, 62, 44.
16. (b) Ungemach, F.; DiPierro, M.; Weber, R.; Cook, J. M. J. Org. Chem. 1981, 46, 164.
17. (c) Soerens, D.; Sandrin, J.; Ungemach, F.; Mokry, P.; Wu, G. S.; Yamanaka, E.; Hutchins, L.; Dipierro, M.; Cook, J. M. J. Org. Chem. 1979, 44, 535.
18. (d) Jackson, A. H.; Smith, A. E. Tetrahedron 1968, 24, 403.
19. (e) Jackson, A. H.; Naidoo, B.; Smith, P. Tetrahedron 1968, 24, 6119.
20. (f) Kawate, T.; Nakagawa, M.; Ogata, K.; Hino, T. Heterocycles 1992, 33, 801.
21. (g) Ungemach, F.; Cook, J. M. Heterocycles 1978, 9, 1089 and references cited therein.
22. (a) Chi, D. Y.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1993, 115, 7045.
23. (b) Chi, D. Y.; O'Neil, J. P.; Anderson, C. J.; Welch, M. J.; Katzenellenbogen, J. A. J. Med. Chem. 1994, 37, 928.
24. (c) Hom, R. K.; Katzenellenbogen, J. A. Nucl. Med. Biol. 1997, 24, 485.
25. (d) Skaddan, M. B.; Katzenellenbogen, J. A. Bioconjugate Chem. 1999, 10, 119.
26. (e) Skaddan, M. B.; Wust, F. R.; Katzenellenbogen, J. A. J. Org. Chem. 1999, 64, 8108.
27. If one considers that a p-methoxystyrene is a trienol system and that reactions of enols with imines are termed Mannich reactions, then the reaction described in this report could be considered a vinylogous Mannich reaction. However, this term is currently employed by Martin to illustrate the nucleophilic addition of 2-trialkylsiloxy furans to cyclic iminium ions; cf. Martin, S. F. et al. J. Am. Chem. Soc. 1996, 118, 3299 and Martin, S. F. et al. J. Am. Chem. Soc. 1999, 121, 6990. It should also be noted that Overman has described a related intramolecular Mannich reaction; cf. Loegers, M. et al. J. Am. Chem. Soc. 1995, 117, 9139 and references cited therein.
28. If one considers that a p-methoxystyrene is a trienol system and that reactions of enols with imines are termed Mannich reactions, then the reaction described in this report could be considered a vinylogous Mannich reaction. However, this term is currently employed by Martin to illustrate the nucleophilic addition of 2-trialkylsiloxy furans to cyclic iminium ions; cf. Martin, S. F. et al. J. Am. Chem. Soc. 1996, 118, 3299 and Martin, S. F. et al. J. Am. Chem. Soc. 1999, 121, 6990. It should also be noted that Overman has described a related intramolecular Mannich reaction; cf. Loegers, M. et al. J. Am. Chem. Soc. 1995, 117, 9139 and references cited therein.
29. If one considers that a p-methoxystyrene is a trienol system and that reactions of enols with imines are termed Mannich reactions, then the reaction described in this report could be considered a vinylogous Mannich reaction. However, this term is currently employed by Martin to illustrate the nucleophilic addition of 2-trialkylsiloxy furans to cyclic iminium ions; cf. Martin, S. F. et al. J. Am. Chem. Soc. 1996, 118, 3299 and Martin, S. F. et al. J. Am. Chem. Soc. 1999, 121, 6990. It should also be noted that Overman has described a related intramolecular Mannich reaction; cf. Loegers, M. et al. J. Am. Chem. Soc. 1995, 117, 9139 and references cited therein.
30. Refer to ref 3b-d.
31. Refer to ref 4.
32. Geier, M.; Hesse, M. Synthesis 1990, 56.
33. Similar temperature affects have been observed in the Pictet - Spengler reaction of tryptamines carried out in nonacidic, aprotic media; cf. ref 7c.
34. Luettrinhaus, A. Justus. Liebigs Ann. Chem. 1963, 661, 84.
35. Kirkpatrick, A.; Maclaren, J. A. Aust. J. Chem. 1983, 36, 833.
36. (a) Barillier, D.; Strobel, M. P.; Morin, L.; Paquer, D. Tetrahedron 1983, 39, 767.
37. (b) Kozerski, L.; Kawecki, R.; Hansen, P. E. Magn. Reson. Chem. 1994, 32, 517.
38. D'Angelo, J.; Gomez-Pardo, D. Tetrahedron Lett. 1991, 32, 3063.
39. TFA is known to cause C(1)-N(2) bond cleavage in methoxysubstituted tetrahydro-β-carbolines through a carbocation-mediated mechanism; cf. ref 7a and Reedy, S. M.; Cook, J. M. Tetrahedron Lett. 1994, 35, 5413.
40. Henin, J.; Vercauteren, J.; Mangenot, C.; Henin, B.; Nuzillard, J. M.; Guilhem, J. Tetrahedron 1999, 55, 9817.
41. (a) Bailey, P. D.; Hollinshead, S. P.; Dauter, Z. J. Chem. Soc., Chem. Commun. 1985, 21, 1507.
42. (b) Vercauteren, J.; Lavaud, C.; Levy, J.; Massiot, G.; Fac. Pharm, R. F. J. Org. Chem. 1984, 49, 2278.