Intramolecular nucleophilic substitution at the C-4 position of functionalized oxetanes: A ring expansion for the construction of various heterocycles

Journal of Organic Chemistry

Volumn 61, Issue 22, 1996, Pages 7642-7643

  Bach, Thorsten ^a   Kather, Kristian ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

FURAN DERIVATIVE; HETEROCYCLIC COMPOUND; PYRAN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0029847587     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961436t     Document Type: Article

References (27)

1. Some selected examples of an exo ring opening by heteroatom nucleophiles follow. (a) N-Nucleophiles: Kozikowski, A. P.; Schmiesing, R. J. Chem. Soc., Chem. Commun. 1979, 106. Tanner, D.; Somfai, P. Tetrahedron Lett. 1985, 26, 3883. McIntosh, J. M.; Matassa, L. C. J. Org. Chem. 1988, 53, 4452. Pearson, W. H.; Bergmeier, S. C. ibid. 1991, 56, 1976. (b) O-Nucleophiles: Kitamura, M.; Isobe, M.; Ichikawa, Y.; Goto, T. J. Am. Chem. Soc. 1984, 106, 3252. Corey, E. J.; Ha, D.-C. Tetrahedron Lett. 1988, 29, 3171. Paterson, I.; Craw, P. A. Ibid. 1989, 30, 5799.
2. Some selected examples of an exo ring opening by heteroatom nucleophiles follow. (a) N-Nucleophiles: Kozikowski, A. P.; Schmiesing, R. J. Chem. Soc., Chem. Commun. 1979, 106. Tanner, D.; Somfai, P. Tetrahedron Lett. 1985, 26, 3883. McIntosh, J. M.; Matassa, L. C. J. Org. Chem. 1988, 53, 4452. Pearson, W. H.; Bergmeier, S. C. ibid. 1991, 56, 1976. (b) O-Nucleophiles: Kitamura, M.; Isobe, M.; Ichikawa, Y.; Goto, T. J. Am. Chem. Soc. 1984, 106, 3252. Corey, E. J.; Ha, D.-C. Tetrahedron Lett. 1988, 29, 3171. Paterson, I.; Craw, P. A. Ibid. 1989, 30, 5799.
3. Some selected examples of an exo ring opening by heteroatom nucleophiles follow. (a) N-Nucleophiles: Kozikowski, A. P.; Schmiesing, R. J. Chem. Soc., Chem. Commun. 1979, 106. Tanner, D.; Somfai, P. Tetrahedron Lett. 1985, 26, 3883. McIntosh, J. M.; Matassa, L. C. J. Org. Chem. 1988, 53, 4452. Pearson, W. H.; Bergmeier, S. C. ibid. 1991, 56, 1976. (b) O-Nucleophiles: Kitamura, M.; Isobe, M.; Ichikawa, Y.; Goto, T. J. Am. Chem. Soc. 1984, 106, 3252. Corey, E. J.; Ha, D.-C. Tetrahedron Lett. 1988, 29, 3171. Paterson, I.; Craw, P. A. Ibid. 1989, 30, 5799.
4. Some selected examples of an exo ring opening by heteroatom nucleophiles follow. (a) N-Nucleophiles: Kozikowski, A. P.; Schmiesing, R. J. Chem. Soc., Chem. Commun. 1979, 106. Tanner, D.; Somfai, P. Tetrahedron Lett. 1985, 26, 3883. McIntosh, J. M.; Matassa, L. C. J. Org. Chem. 1988, 53, 4452. Pearson, W. H.; Bergmeier, S. C. ibid. 1991, 56, 1976. (b) O-Nucleophiles: Kitamura, M.; Isobe, M.; Ichikawa, Y.; Goto, T. J. Am. Chem. Soc. 1984, 106, 3252. Corey, E. J.; Ha, D.-C. Tetrahedron Lett. 1988, 29, 3171. Paterson, I.; Craw, P. A. Ibid. 1989, 30, 5799.
5. Some selected examples of an exo ring opening by heteroatom nucleophiles follow. (a) N-Nucleophiles: Kozikowski, A. P.; Schmiesing, R. J. Chem. Soc., Chem. Commun. 1979, 106. Tanner, D.; Somfai, P. Tetrahedron Lett. 1985, 26, 3883. McIntosh, J. M.; Matassa, L. C. J. Org. Chem. 1988, 53, 4452. Pearson, W. H.; Bergmeier, S. C. ibid. 1991, 56, 1976. (b) O-Nucleophiles: Kitamura, M.; Isobe, M.; Ichikawa, Y.; Goto, T. J. Am. Chem. Soc. 1984, 106, 3252. Corey, E. J.; Ha, D.-C. Tetrahedron Lett. 1988, 29, 3171. Paterson, I.; Craw, P. A. Ibid. 1989, 30, 5799.
6. Some selected examples of an exo ring opening by heteroatom nucleophiles follow. (a) N-Nucleophiles: Kozikowski, A. P.; Schmiesing, R. J. Chem. Soc., Chem. Commun. 1979, 106. Tanner, D.; Somfai, P. Tetrahedron Lett. 1985, 26, 3883. McIntosh, J. M.; Matassa, L. C. J. Org. Chem. 1988, 53, 4452. Pearson, W. H.; Bergmeier, S. C. ibid. 1991, 56, 1976. (b) O-Nucleophiles: Kitamura, M.; Isobe, M.; Ichikawa, Y.; Goto, T. J. Am. Chem. Soc. 1984, 106, 3252. Corey, E. J.; Ha, D.-C. Tetrahedron Lett. 1988, 29, 3171. Paterson, I.; Craw, P. A. Ibid. 1989, 30, 5799.
7. Some selected examples of an exo ring opening by heteroatom nucleophiles follow. (a) N-Nucleophiles: Kozikowski, A. P.; Schmiesing, R. J. Chem. Soc., Chem. Commun. 1979, 106. Tanner, D.; Somfai, P. Tetrahedron Lett. 1985, 26, 3883. McIntosh, J. M.; Matassa, L. C. J. Org. Chem. 1988, 53, 4452. Pearson, W. H.; Bergmeier, S. C. ibid. 1991, 56, 1976. (b) O-Nucleophiles: Kitamura, M.; Isobe, M.; Ichikawa, Y.; Goto, T. J. Am. Chem. Soc. 1984, 106, 3252. Corey, E. J.; Ha, D.-C. Tetrahedron Lett. 1988, 29, 3171. Paterson, I.; Craw, P. A. Ibid. 1989, 30, 5799.
8. Some selected examples of an endo ring opening by heteroatom nucleophiles follow. (a) N-Nucleophiles: Setoi, H.; Takeno, H.; Hashimoto, M. Tetrahedron Lett. 1985, 26, 4617. Ratovelomanana, V.; Vidal, L.; Royer, J.; Husson, H.-P. Heterocycles 1991, 32, 879. (b) O-Nucleophiles: Chmielewski, M.; Guzik, P. Heterocycles 1984, 22, 7. Nicolaou, K. C.; Prasad, C. V. C.; Somers, P. K.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 5330.
9. Some selected examples of an endo ring opening by heteroatom nucleophiles follow. (a) N-Nucleophiles: Setoi, H.; Takeno, H.; Hashimoto, M. Tetrahedron Lett. 1985, 26, 4617. Ratovelomanana, V.; Vidal, L.; Royer, J.; Husson, H.-P. Heterocycles 1991, 32, 879. (b) O-Nucleophiles: Chmielewski, M.; Guzik, P. Heterocycles 1984, 22, 7. Nicolaou, K. C.; Prasad, C. V. C.; Somers, P. K.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 5330.
10. Some selected examples of an endo ring opening by heteroatom nucleophiles follow. (a) N-Nucleophiles: Setoi, H.; Takeno, H.; Hashimoto, M. Tetrahedron Lett. 1985, 26, 4617. Ratovelomanana, V.; Vidal, L.; Royer, J.; Husson, H.-P. Heterocycles 1991, 32, 879. (b) O-Nucleophiles: Chmielewski, M.; Guzik, P. Heterocycles 1984, 22, 7. Nicolaou, K. C.; Prasad, C. V. C.; Somers, P. K.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 5330.
11. Some selected examples of an endo ring opening by heteroatom nucleophiles follow. (a) N-Nucleophiles: Setoi, H.; Takeno, H.; Hashimoto, M. Tetrahedron Lett. 1985, 26, 4617. Ratovelomanana, V.; Vidal, L.; Royer, J.; Husson, H.-P. Heterocycles 1991, 32, 879. (b) O-Nucleophiles: Chmielewski, M.; Guzik, P. Heterocycles 1984, 22, 7. Nicolaou, K. C.; Prasad, C. V. C.; Somers, P. K.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 5330.
12. Yamaguchi, M.; Hirao, I. Tetrahedron Lett. 1984, 25, 4549.
13. Itoh, A.; Hirose, Y.; Kashiwagi, H.; Masaki, Y. Heterocycles 1994, 38, 2165.
14. Danishefsky, S. J.; Masters, J. J.; Young, W. B.; Link, J. T.; Snyder, L. B.; Magee, T. V.; Jung, D. K.; Isaacs, R. C. A.; Bornmann, W. G.; Alaimo, C. A.; Coburn, C. A.; Di Grandi, M. J. J. Am. Chem. Soc. 1996, 118, 2843.
15. Khan, N.; Morris, T. H.; Smith, E. H.; Walsh, R. J. Chem. Soc., Perkin Trans. 1 1991, 865.
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17. (b) Mead, K. T.; Lu, J. Tetrahedron Lett. 1994, 35, 8947.
18. (a) Bach, T.; Jödicke, K. Chem. Ber. 1993, 126, 2457.
19. (b) Bach, T. Liebigs Ann. 1995, 855 and references cited therein.
20. Kather, K. Ph.D. thesis, University of Münster, 1996. Starting from ethyl 5-oxohexanoate the procedure is identical to the one employed for the construction of oxetane 1a (cf. ref 8b).
21. Volante, R. P. Tetrahedron Lett. 1981, 22, 3119.
22. Henry, J. R.; Marcin, L. R.; McIntosh, M. C.; Scola, P. M.; Harris, G. D., Jr.; Weinreb, S. M. Tetrahedron Lett. 1989, 30, 5709.
23. Rawal, V. H.; Jones, R. J.; Cava, M. P. J. Org. Chem. 1987, 52, 19.
24. The amide 4 was prepared from TsNCO and 9-fluorenylmethanol (solvent: toluene; 93% yield) in full analogy to a previously described procedure (cf. ref 11).
25. 2O was used. If no silylated product was detected by TLC and NMR the desilylation procedure was omitted.
26. For the biological relevance of closely related compounds, see: Hite, G.; Lokhandwala, M.; Patel, D. B.; Patel, H.; Merker, P. C.; Shafi'ee, A. J. Pharm. Sci. 1971, 60, 685.
27. Hurst, D. T.; McInnes, A. G. Can. J. Chem. 1965, 43, 2004.