Intramolecular electrophilic aromatic substitution reactions of 2-amidoacroleins: A new method for the preparation of tetrahydroisoquinolines, tetrahydro-3-benzazepines, and hexahydro-3-benzazocines

Organic Letters

Volumn 3, Issue 21, 2001, Pages 3349-3351

  Fuchs, James R ^a   Funk, Raymond L ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,3,4-TETRAHYDROISOQUINOLINE; ACROLEIN; AZOCINE DERIVATIVE; BENZAZEPINE DERIVATIVE; DRUG DERIVATIVE; ISOQUINOLINE DERIVATIVE; MORPHINE DERIVATIVE; TETRAHYDROISOQUINOLINE; TETRAHYDROISOQUINOLINE DERIVATIVE;

ARTICLE; CHEMISTRY; SYNTHESIS;

ACROLEIN; AZOCINES; BENZAZEPINES; ISOQUINOLINES; MORPHINE DERIVATIVES; TETRAHYDROISOQUINOLINES;

EID: 0035909641     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016592n     Document Type: Article

References (29)

1. (a) Bentley, K. W. Nat. Prod. Rep. 2001, 18, 148 and previous reviews therein.
2. (b) The Merck Index, 12th ed.; Budavari, S., Ed.; Merck & Co., Inc.: Whitehouse Station, NJ, 1996.
3. (a) Maeng, J.-H.; Funk, R. L. Org. Lett. 2000, 3, 1125.
4. (b) Funk, R. L.; Greshock, T. J., submitted for publication.
5. For selected examples of Lewis acid mediated intramolecular electrophilic aromatic substitution reactions using unsaturated carbonyl compounds, see: endo carbonyl (a) Smith, L. I.; Prichard, W. W. J. Am. Chem. Soc. 1940, 62, 778.
6. (b) Colonge, J.; Chambard, R. Bull. Soc. Chem. Fr. 1953, 982.
7. (c) Parham, W. E.; Wheeler, E. L.; Dodson, R. M. J. Am. Chem. Soc. 1955, 77, 1166.
8. (d) Pandey, R. C.; Dev, S. Tetrahedron 1968, 24, 3829.
9. (e) Dawson, M. I.; Hobbs, P. D.; Derdzinski, K.; Chan, R. L.; Gruber J.; Chao, W.; Smith, S.; Thies, R. W.; Schiff, L. J. J. Med. Chem. 1984, 27, 1516.
10. (f) Janusz, J. M.; Young, P. A.; Scherz, M. W.; Enzweiler, K.; Wu, L. I.; Gan, L.; Pikul, S.; McDow-Dunham, K. L.; Johnson, C. R.; Senanayake, C. B.; Kellstein, D. E.; Green, S. A.; Tulich, J. L.; Rosario-Jansen, T.; Magrisso, I. J.; Wehmeyer, K. R.; Kuhlenbeck, D. L.; Eichold, T. H.; Dobson, R. L. M. J. Med. Chem. 1998, 41, 1124.
11. (g) Bergman, J.; Venemalm, L.; Gogoll, A. Tetrahedron 1990, 46, 6067.
12. (h) Nagao, Y.; Lee, W. S.; Komaki, Y.; Sano, S.; Shiro, M. Chem. Lett. 1994, 597.
13. (i) Ho, T.-L.; Yang, P.-F. Tetrahedron 1995, 51, 181. exo carbonyl
14. (j) Stork, G.; Burgstahler, A. J. Am. Chem. Soc. 1951, 73, 3544.
15. (k) Murphy, W. S.; Watanasin, S. J. Chem. Soc., Perkin Trans, 1 1980, 1555.
16. (l) Jung, M. E.; Lam, P. Y.-S.; Mansuri, M. M.; Speltz, L. M. J. Org. Chem. 1985, 50, 1087.
17. (m) Kashihara, H.; Shinoki, H.; Suemune, H.; Sakai, K. Chem. Pharm. Bull. 1986, 11, 4527.
18. (n) Hauser, F. M.; Caringal, Y. J. Org. Chem. 1990, 55, 555.
19. For the photocyclization of a 2-(benzamido)acrylates, see: (a) Schultz, A. G.; Sha, C.-K. Tetrahedron 1980, 36, 1757.
20. (b) Naito, T.; Ninomiya, I. Heterocycles 1988, 27, 1325.
21. (c) Pyne, S. G.; Schafer, K. Tetrahedron 1998, 54, 5709. For the intramolecular Heck reactions of 2-{N-[(iodoaryl)alkyl]-N-(tert-butoxycarbonyl)-amino}acrylates, see:
22. (d) Gibson, S. E.; Guillo, N.; Middleton, R. J.; Thuilliez, A.; Tozer, M. J. J. Chem. Soc., Perkin Trans. 1 1997, 447.
23. Prepared in two steps from tris(hydroxymethyl)aminomethane hydrochloride. Hoppe, D.; Schmincke, H.; Kleemann, H.-W. Tetrahedron 1989, 45, 687.
24. Hendrickson, J. B.; Bergeron, R.; Sternbach, D. D. Tetrahedron 1975, 31, 2517.
25. (b) Hendrickson, J. B.; Bair, K. W.; Bergeron, R.; Giga, A.; Skipper, P. L.; Sternbach, D. D.; Wareing, J. A. Org. Prep. Proced. Int. 1977, 9, 173.
26. 3-Benzazocine analogues of morphine similar to 16 but lacking the dihydrofuran ring have been previously reported; see: (a) Pecherer, B.; Stumpf, J.; Brossi, A. Helv. Chim. Acta 1970, 53, 763.
27. (b) Hori, M.; Kataoka, T.; Shimizu, H.; Imai, E.; Koide, T.; Iwata, N.; Kurono, M. Chem. Pharm. Bull. 1990, 38, 8.
28. (c) Lai, B.; Bhedi, D. N.; Gidwani, R. M.; Sankar, C. Tetrahedron 1994, 50, 9167 and ref 1 therein. Moreover, molecular mechanics calculations suggest that the dihydrofuran ring as well as the hydroxymethyl substituent of 14 contribute to the significant population of the morphine-like conformer shown (0.75 kcal/mol above global minimum, 8% of a Boltzmann distribution of all conformers at 300 °K).
29. Benzazocines 14 and 16 have been submitted for biological evaluation. These studies will be reported separately.