1,2,6-Trisubstituted Tetrahydroisoquinoline Derivatives by Solid-Phase Synthesis

Synlett

Volumn 1996, Issue 11, 1996, Pages 1036-1038

  Rolfing K ^a   Thiel, M ^a   Kunzer H ^a  

^a BAYER PHARMA AG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0342371152     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5680     Document Type: Article

References (19)

1. (a) Früchtel, J. S.; Jung, G. Angew. Chem. 1996, 108, 19; Angew. Chem., Int. Ed. Engl. 1996, 35, 17.
2. (a) Früchtel, J. S.; Jung, G. Angew. Chem. 1996, 108, 19; Angew. Chem., Int. Ed. Engl. 1996, 35, 17.
3. (b) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555.
4. (c) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527.
5. (a) Hobbs DeWitt, S.; Czarnik, A. W. Acc. Chem. Res. 1996, 29, 114.
6. (b) Dressman, B. A.; Spangle, L. A.; Kaldor, S. W. Tetrahedron Lett. 1996, 37, 937.
7. (c) Ellman, J. A. Acc. Chem. Res. 1996, 29, 132.
8. (d) Gordon, E. M.; Gallop, M. A.; Patel, D. V. Acc. Chem. Res. 1996, 29, 144.
9. For a comprehensive treatise on isoquinolines, consult: Isoquinolines, Part 3; Coppola, G. M., Schuster, H. F., Eds.; Vol. 38 in the series The Chemistry of Heterocyclic Compounds; Weissberger, A., Taylor, E. C., Eds.; Wiley-Interscience: New York, 1995. See also Part 1 and Part 2.
10. Recent examples of pharmacologically interesting tetrahydroisoquinolines include: (a) Kase, H.; Fujita, H.; Nakamura, J.; Hashizume, K.; Goto, J.; Kubo, K.; Shuto, K. J. Antibiot. 1986, 39, 354. (b) Vizi, E. S.; Toth, I.; Somogyi, G. T.; Szabo, L.; Harsing, L. G.; Szantay, C. J. Med. Chem. 1987, 30, 1355. (c) Minor, D. L.; Wyrick, S. D.; Charifson, P. S.; Watts, V. J.; Nichols, D. E.; Mailman, R. B. J. Med. Chem. 1994, 37, 4317.
11. Recent examples of pharmacologically interesting tetrahydroisoquinolines include: (a) Kase, H.; Fujita, H.; Nakamura, J.; Hashizume, K.; Goto, J.; Kubo, K.; Shuto, K. J. Antibiot. 1986, 39, 354. (b) Vizi, E. S.; Toth, I.; Somogyi, G. T.; Szabo, L.; Harsing, L. G.; Szantay, C. J. Med. Chem. 1987, 30, 1355. (c) Minor, D. L.; Wyrick, S. D.; Charifson, P. S.; Watts, V. J.; Nichols, D. E.; Mailman, R. B. J. Med. Chem. 1994, 37, 4317.
12. Recent examples of pharmacologically interesting tetrahydroisoquinolines include: (a) Kase, H.; Fujita, H.; Nakamura, J.; Hashizume, K.; Goto, J.; Kubo, K.; Shuto, K. J. Antibiot. 1986, 39, 354. (b) Vizi, E. S.; Toth, I.; Somogyi, G. T.; Szabo, L.; Harsing, L. G.; Szantay, C. J. Med. Chem. 1987, 30, 1355. (c) Minor, D. L.; Wyrick, S. D.; Charifson, P. S.; Watts, V. J.; Nichols, D. E.; Mailman, R. B. J. Med. Chem. 1994, 37, 4317.
13. For a recent polymer-supported synthesis of tetrahydroisoquinolines derived from (L)-3,4-dimethoxyphenylalanine, see: Meutermans, W. D. F.; Alewood, P. F. Tetrahedron Lett. 1995, 36, 7709. For a β-carboline synthesis on solid support, see: Kaljuste, K.; Undén, A. Tetrahedron Lett. 1995, 36, 9211.
14. For a recent polymer-supported synthesis of tetrahydroisoquinolines derived from (L)-3,4-dimethoxyphenylalanine, see: Meutermans, W. D. F.; Alewood, P. F. Tetrahedron Lett. 1995, 36, 7709. For a β-carboline synthesis on solid support, see: Kaljuste, K.; Undén, A. Tetrahedron Lett. 1995, 36, 9211.
15. Whaley, W. M.; Govindachari, T. R. In Organic Reactions, Vol. 6; Adams, R., Ed.; Wiley & Sons, Inc.: New York, 1951; Chapter 2.
16. (a) Basha, A.; Lipton, M.; Weinreb, S. M. Tetrahedron Lett. 1977, 18, 4171.
17. (b) Ley, S. V.; Mynett, D. M.; Koot, W.-J. Synlett 1995, 1017.
18. Darling, G. D.; Fréchet, J. M. J. J. Org. Chem. 1986, 51, 2270. 2-Hydroxyethyl polystyrene is commercially available from Rapp Polymere GmbH, Ernst Simon Str. 9, D-72072 Tübingen, Germany.
19. 3) δ 173.1, 157.0, 145.0, 136.1, 131.0, 129.9, 129.7, 127.9, 126.8, 113.2, 112.5, 69.0, 67.8, 62.6, 47.5, 46.8, 37.0, 29.5, 29.4, 29.3,28.5, 26.1, 26.0, 25.9, 21.0, 20.5, 20.1.