Heterocycle annulation of enolizable vinyl quinone imides. Dihydroquinolines and quinolines from thermal 6π-electrocyclizations and indoles from photochemical cyclizations

Organic Letters

Volumn 4, Issue 24, 2002, Pages 4265-4268

  Parker, Kathlyn A ^a   Mindt, Thomas L ^b  

^a STONY BROOK UNIVERSITY   (United States)

^b BROWN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

IMIDE; INDOLE DERIVATIVE; QUINOLINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; ELECTROCHEMISTRY; PHOTOCHEMISTRY;

CYCLIZATION; ELECTROCHEMISTRY; IMIDES; INDOLES; MOLECULAR STRUCTURE; PHOTOCHEMISTRY; QUINOLINES;

EID: 0037191612     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026849x     Document Type: Article

References (23)

1. See, e.g.: Jones, G. In Chemistry of Heterocyclic Compounds "Quinolines"; John Wiley & Sons: New York, 1977 (part 1), 1982 (part 2), 1990 (part 3); Vol. 32.
2. Michael, J. P. Nat. Prod. Rep. 2001, 17, 603-620 and previous reviews in this series.
3. (a) Kouznetsov, V.; Palma, A.; Ewert, C.; Varlamov, A. J. Heterocycl. Chem. 1998, 35, 761-785.
4. (b) Evans, P. A.; Robinson, J. E.; Moffett, K. K. Org. Lett. 2001, 3, 3269-3271.
5. See, e.g.: Altamura, M.; Meini, S.; Quartara, L.; Maggi, C. A. Regul. Pept. 1999, 80, 13-26.
6. Parker, K. A., Mindt, T. L. Org. Lett. 2001, 24, 3875-3878.
7. Ortho quinone methide imines (from the thermolytic dehydration of o-(2-hydroxy-3-propenyl) anilines in refluxing xylene or o-dichlorobenzene for several hours) have been reported to undergo electrocyclization to 1,2-dihydroquinolines; see: Wiebe, J. M.; Caille, A. S.; Trimble, L.; Lau, C. K. Tetrahedron 1996, 52, 11705-11724.
8. Stille coupling is reported not to proceed with free arylamines; see: Falcou, A.; Marsacq, D.; Hourquebie, P.; Duchêne, A. Tetrahedron 2000, 56, 225-231. Our own experience confirms this.
9. The synthesis and physical and chemical properties of quinone di-and monoimides are described in the pioneering papers of Roger Adams. See, e.g.: Adams, R.; Reifschneider, W. Bull. Soc. Chim. Fr. 1958, 23-65.
10. Tidwell, J. H.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 11797-11810.
11. Collins, P. W.; Kramer, S. W.; Gasiecki, A. F.; Weier, R. M.; Jones, P. H.; Gullikson, G. W.; Bianchi, R. G. J. Med. Chem. 1987, 30, 193-197.
12. SES = trimethylsilylethanesulfonyl (Weinreb, S. M.; Demko, D. M.; Lessen, T. A. Tetrahedron Lett. 1986, 27, 2099-2102).
13. With the diimides, the rate of reaction accelerated with the amount of HMPA added up to approximately 5 vol %.
14. Basic reaction conditions (NaOMe, MeOH) left dihydroquinoline 9a unchanged, whereas acidic conditions (AcOH or up to 37% HCl) resulted in the formation of decomposition products.
15. Total syntheses of each of these targets have been reported. For quinine, see: Stork, G.; Niu, D.; Fujimoto, A.; Koft, E. R.; Balkovec, J. M.; Tata, J. R.; Dake, G. R. J. Am. Chem. Soc. 2001, 123, 3239-3242. For streptonigrin, see: Boger, D. L.; Panek, J. S.; Duff, S. R. J. Am. Chem. Soc. 1985, 107, 5745-54. For luzopeptins, see: Boger, D. L.; Ledeboer, M. W.; Kume, M.; Searcey, M.; Jin, Q. J. Am. Chm. Soc. 1999, 121, 11375-11383. Valognes, D.; Belmont, P.; Xi, N.; Ciufolini, M. A. Tetrahedron Lett. 2001, 42, 1907-1909.
16. Total syntheses of each of these targets have been reported. For quinine, see: Stork, G.; Niu, D.; Fujimoto, A.; Koft, E. R.; Balkovec, J. M.; Tata, J. R.; Dake, G. R. J. Am. Chem. Soc. 2001, 123, 3239-3242. For streptonigrin, see: Boger, D. L.; Panek, J. S.; Duff, S. R. J. Am. Chem. Soc. 1985, 107, 5745-54. For luzopeptins, see: Boger, D. L.; Ledeboer, M. W.; Kume, M.; Searcey, M.; Jin, Q. J. Am. Chm. Soc. 1999, 121, 11375-11383. Valognes, D.; Belmont, P.; Xi, N.; Ciufolini, M. A. Tetrahedron Lett. 2001, 42, 1907-1909.
17. Total syntheses of each of these targets have been reported. For quinine, see: Stork, G.; Niu, D.; Fujimoto, A.; Koft, E. R.; Balkovec, J. M.; Tata, J. R.; Dake, G. R. J. Am. Chem. Soc. 2001, 123, 3239-3242. For streptonigrin, see: Boger, D. L.; Panek, J. S.; Duff, S. R. J. Am. Chem. Soc. 1985, 107, 5745-54. For luzopeptins, see: Boger, D. L.; Ledeboer, M. W.; Kume, M.; Searcey, M.; Jin, Q. J. Am. Chm. Soc. 1999, 121, 11375-11383. Valognes, D.; Belmont, P.; Xi, N.; Ciufolini, M. A. Tetrahedron Lett. 2001, 42, 1907-1909.
18. Total syntheses of each of these targets have been reported. For quinine, see: Stork, G.; Niu, D.; Fujimoto, A.; Koft, E. R.; Balkovec, J. M.; Tata, J. R.; Dake, G. R. J. Am. Chem. Soc. 2001, 123, 3239-3242. For streptonigrin, see: Boger, D. L.; Panek, J. S.; Duff, S. R. J. Am. Chem. Soc. 1985, 107, 5745-54. For luzopeptins, see: Boger, D. L.; Ledeboer, M. W.; Kume, M.; Searcey, M.; Jin, Q. J. Am. Chm. Soc. 1999, 121, 11375-11383. Valognes, D.; Belmont, P.; Xi, N.; Ciufolini, M. A. Tetrahedron Lett. 2001, 42, 1907-1909.
19. For the preparation of protected amino phenols 12a and 12b, see Supporting Information.
20. Employment of higher concentrations of HMPA resulted in the formation of mixtures of dihydroquinoline and indole products.
21. The formation of indole products from diimide substrates 8a and 8b was not observed even after prolonged exposure to light or upon irradiation in a photochemical reactor in toluene containing HMPA.
22. Related indoles have been used in nonpeptidic neurotensin mimetics; see: Dodd, D. S.; Kozikowski, A. P.; Cusack, B.; Richelson, E. Bioorg. Med. Chem. Lett. 1994, 4, 1241-1246.
23. Iwamoto, H.; Takuwa, A.; Hamada, K.; Fujiwara, R. J. Chem. Soc., Perkin Trans. 1 1999, 575-581.