Synthesis of 4-Ethyloctahydroindolo[2,3-a]quinolizine-2-carbaldehydes

Tetrahedron

Volumn 53, Issue 27, 1997, Pages 9407-9414

  Bonjoch, Josep ^a   Fernàndez, Joan Carles ^a   Terricabras, Dolors ^a   Valls, Nativitat ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE ALKALOID;

ARTICLE; CHEMICAL REACTION; CONFORMATION; CYCLIZATION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; STEREOISOMERISM;

EID: 0343051976     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00593-0     Document Type: Article

References (28)

1. Fernàndez, J.-C.; Valls, N.; Bosch, J.; Bonjoch, J. J. Chem. Soc., Chem. Commun. 1995, 2317-2318.
2. (a) Lounasmaa, M.; Tolvanen, A. "The Corynantheine-Heteroyohimbine Group" in Monoterpenoid Indole Alkaloids, Supplement to Part 4, Saxton J. E. ed., in The Chemistry of Heterocyclic Compounds, Taylor, E. C., ed., chapter 3, John Wiley, Chichester, 1994;
3. (b) Szántay, C.; Nemes, A. "The Eburnamine-Vincamine Group" in Monoterpenoid Indole Alkaloids, Supplement to Part 4, Saxton J. E. ed., in The Chemistry of Heterocyclic Compounds, Taylor, E. C., ed., chapter 9, John Wiley, Chichester, 1994.
4. There are no precedents for the synthesis of 2,4-dialkylsubstituted octahydroindolo[2,3-a]quinolizines. The preparation of 2-oxo-4-alkyl derivatives in this series using an imino Diels-Alder process has been recently reported: Waldmann, H.; Braun, M.; Weymann, M.; Gewehr, M. Tetrahedron 1993, 49, 397-414; Lock, R.; Waldmann, H. Chem. Eur. J. 1997, 3, 143-151.
5. There are no precedents for the synthesis of 2,4-dialkylsubstituted octahydroindolo[2,3-a]quinolizines. The preparation of 2-oxo-4-alkyl derivatives in this series using an imino Diels-Alder process has been recently reported: Waldmann, H.; Braun, M.; Weymann, M.; Gewehr, M. Tetrahedron 1993, 49, 397-414; Lock, R.; Waldmann, H. Chem. Eur. J. 1997, 3, 143-151.
6. For the synthesis of 2-cyanotetrahydropyridines from pyridinium salts, see: a) Fry, E. M. J. Org. Chem. 1964, 29, 1647-1650;
7. b) Feliz, M.; Bosch, J; Mauleón, D.; Amat, M.; Domingo, A. J. Org. Chem. 1982, 47, 2435-2440.
8. c) Lounasmaa, M.; Jokela, R. Heterocycles 1990, 31, 1351-1358.
9. For some examples of Grignard reagents upon α-aminonitriles, see: (a) Bosch, J.; Alvarez, M.; Llobera, R.; Feliz, M. An. Quím 1979, 75, 712-717.
10. (b) Bonin, M.; Romero, J. R.; Grierson, D. S.; Husson, H.-P. J. Org. Chem. 1984, 49, 2392-2400.
11. (c) Polniaszek, R. P.; Belmont, S. E. J. Org. Chem. 1990, 55, 4688-4693.
12. (d) Yue, C.; Gauthier, I.; Royer, J.; Husson, H.-P. J. Org. Chem. 1996, 61, 4949-4954.
13. For some examples of organolithium reagents upon α-aminonitriles, see: McElroy, A. B.; Bays, D. E.; Scopes, D. I. C.; Hayes, A. G.; Sheehan, M. J. J. Chem. Soc., Perkin Trans 1, 1990, 1563-1571; Bennasar, M.-L.; Zulaica, E.; Bonjoch, J.; Bosch, J. Tetrahedron 1991, 47, 5507-5512. See also ref 5a.
14. For some examples of organolithium reagents upon α-aminonitriles, see: McElroy, A. B.; Bays, D. E.; Scopes, D. I. C.; Hayes, A. G.; Sheehan, M. J. J. Chem. Soc., Perkin Trans 1, 1990, 1563-1571; Bennasar, M.-L.; Zulaica, E.; Bonjoch, J.; Bosch, J. Tetrahedron 1991, 47, 5507-5512. See also ref 5a.
15. 2N), 60.0 (C-2), 105.1 (OCHO), 111.1 (C-7), 114.5 (C-3′), 118.8 (C-4′), 119.1 (C-5′), 121.6 (C-2′), 122.0 (C-2), 127.5 (C-3a), 128.0 (C-3), 133.5 (C-4), 136.2 (C-7a).
16. For the synthesis of octahydroindolo[2,3-a]quinolizines by means of acid isomerization of tetrahydropyridine derivatives with an electron-withdrawing substituent at C-4, see: (a) Allen, M. S.; Gaskell, A. J.; Joule, J. A. J. Chem. Soc. 1971, 736-43.
17. (b) Massiot, G.; Cherif, A. Bull. Soc. Chim. Fr. 1990, 648-55.
18. 1,8b this competitive pathway was not observed, suggesting that the α-ethyl substituent in the iminium salt intermediate slows down the cyclization process.
19. Huet, F. Lechevallier, A.; Pellet, M. Conia, J.-M. Synthesis 1976, 63-65
20. (a) Lounasmaa, M.; Karvinen, E. Tetrahedron 1991, 47, 6371-6380.
21. (b) Amann, R.; Arnold, K.; Spitzner, D.; Majer, Z.; Snatzke, G. Liebigs Ann. 1996, 349-355.
22. (a) Tourwé, D.; Van Binst, G. Heterocycles 1978, 9, 507-533.
23. (b) Lounasmaa, M.; Jokela, R.; Hanhinen, P.; Miettinen, J.; Salo, J. Tetrahedron 1994, 50, 9207-9222 and references therein.
24. Gribble, G. W.; Nelson, R. B.; Johnson, J. L.; Levy, G. C. J. Org. Chem. 1975, 40, 3720-3725. Lounasmaa, M.; Jokela, R. Tetrahedron 1989, 45, 3975-3991.
25. Gribble, G. W.; Nelson, R. B.; Johnson, J. L.; Levy, G. C. J. Org. Chem. 1975, 40, 3720-3725. Lounasmaa, M.; Jokela, R. Tetrahedron 1989, 45, 3975-3991.
26. Uskokovic, M.; Bruderer, H.; von Planta, C.; Williams, T.; Brossi, A. J. Am. Chem. Soc. 1964, 86, 3364-3367.
27. Prepared by a extension of a method developed: Bodor, N.; Shek, E.; Higuchi, T. J. Med. Chem. 1976, 19, 102-107
28. 2, 0 °C).