High-pressure organic chemistry. 19. High-pressure-promoted, silica gel-catalyzed reaction of epoxides with nitrogen heterocycles

Journal of Organic Chemistry

Volumn 61, Issue 3, 1996, Pages 984-990

  Kotsuki, Hiyoshizo ^a   Hayashida, Katsunori ^a   Shimanouchi, Tomoyasu ^a   Nishizawa, Hitoshi ^a  

^a KOCHI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000397241     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951106t     Document Type: Article

References (52)

1. Part 18: Kotsuki, H.; Shimanouchi, T.; Teraguchi, M.; Kataoka, M.; Tatsukawa, A.; Nishizawa, H. Chem. Lett. 1994, 2159.
2. Parker, R. E.; Isaacs, N. S. Chem. Rev. 1959, 59, 737. Buchanan, J. G.; Sable, H. Z. In Selective Organic Transformations; Thyagarajan, B. S., Ed.; Wiley: New York, 1972; Vol. 2, p 1. Rao, A. S.; Paknikar, S. K.; Kirtane, J. G. Tetrahedron 1983, 39, 2323. Smith, J. G. Synthesis 1984, 629. Bonini, C.; Righi, G. Ibid. 1994, 225.
3. Parker, R. E.; Isaacs, N. S. Chem. Rev. 1959, 59, 737. Buchanan, J. G.; Sable, H. Z. In Selective Organic Transformations; Thyagarajan, B. S., Ed.; Wiley: New York, 1972; Vol. 2, p 1. Rao, A. S.; Paknikar, S. K.; Kirtane, J. G. Tetrahedron 1983, 39, 2323. Smith, J. G. Synthesis 1984, 629. Bonini, C.; Righi, G. Ibid. 1994, 225.
4. Parker, R. E.; Isaacs, N. S. Chem. Rev. 1959, 59, 737. Buchanan, J. G.; Sable, H. Z. In Selective Organic Transformations; Thyagarajan, B. S., Ed.; Wiley: New York, 1972; Vol. 2, p 1. Rao, A. S.; Paknikar, S. K.; Kirtane, J. G. Tetrahedron 1983, 39, 2323. Smith, J. G. Synthesis 1984, 629. Bonini, C.; Righi, G. Ibid. 1994, 225.
5. Parker, R. E.; Isaacs, N. S. Chem. Rev. 1959, 59, 737. Buchanan, J. G.; Sable, H. Z. In Selective Organic Transformations; Thyagarajan, B. S., Ed.; Wiley: New York, 1972; Vol. 2, p 1. Rao, A. S.; Paknikar, S. K.; Kirtane, J. G. Tetrahedron 1983, 39, 2323. Smith, J. G. Synthesis 1984, 629. Bonini, C.; Righi, G. Ibid. 1994, 225.
6. Parker, R. E.; Isaacs, N. S. Chem. Rev. 1959, 59, 737. Buchanan, J. G.; Sable, H. Z. In Selective Organic Transformations; Thyagarajan, B. S., Ed.; Wiley: New York, 1972; Vol. 2, p 1. Rao, A. S.; Paknikar, S. K.; Kirtane, J. G. Tetrahedron 1983, 39, 2323. Smith, J. G. Synthesis 1984, 629. Bonini, C.; Righi, G. Ibid. 1994, 225.
7. Pfenninger, A. Synthesis 1986, 89. Hanson, R. M. Chem. Rev. 1991, 91, 437. Schurig, V.; Betschinger, F. Chem. Rev. 1992, 92, 873. Besse, P.; Veschambre, H. Tetrahedron 1994, 50, 8885.
8. Pfenninger, A. Synthesis 1986, 89. Hanson, R. M. Chem. Rev. 1991, 91, 437. Schurig, V.; Betschinger, F. Chem. Rev. 1992, 92, 873. Besse, P.; Veschambre, H. Tetrahedron 1994, 50, 8885.
9. Pfenninger, A. Synthesis 1986, 89. Hanson, R. M. Chem. Rev. 1991, 91, 437. Schurig, V.; Betschinger, F. Chem. Rev. 1992, 92, 873. Besse, P.; Veschambre, H. Tetrahedron 1994, 50, 8885.
10. Pfenninger, A. Synthesis 1986, 89. Hanson, R. M. Chem. Rev. 1991, 91, 437. Schurig, V.; Betschinger, F. Chem. Rev. 1992, 92, 873. Besse, P.; Veschambre, H. Tetrahedron 1994, 50, 8885.
11. March, J. Advanced Organic Chemistry, 4th ed.; Wiley: New York, 1992; p 376.
12. For a general review of our work in this area, see: Kotsuki, H. Kagaku to Kogyo (Osaka) 1994, 68, 265.
13. Kotsuki, H.; Nishiuchi, M.; Kobayashi, S.; Nishizawa, H. J. Org. Chem. 1990, 55, 2969.
14. Bennett, F.; Patel, N M.; Girijavallabhan, V. M.; Ganguly, A. K. Synlett 1993, 703. Raubo, P.; Wicha. J. Synlett 1993, 25.
15. Bennett, F.; Patel, N M.; Girijavallabhan, V. M.; Ganguly, A. K. Synlett 1993, 703. Raubo, P.; Wicha. J. Synlett 1993, 25.
16. McKillop, A.; Young, D. W. Synthesis 1979, 401, 481. Hojo, M. Yuki Gosei Kagaku Kyokaiski 1984, 42, 635. Cornelis, A.; Laszlo, P. Synthesis 1985, 909. Isobe, K.; Yagasaki, A. Acc. Chem. Res. 1993, 26, 524. Corma, A. Chem. Rev. 1995, 95, 559.
17. McKillop, A.; Young, D. W. Synthesis 1979, 401, 481. Hojo, M. Yuki Gosei Kagaku Kyokaiski 1984, 42, 635. Cornelis, A.; Laszlo, P. Synthesis 1985, 909. Isobe, K.; Yagasaki, A. Acc. Chem. Res. 1993, 26, 524. Corma, A. Chem. Rev. 1995, 95, 559.
18. McKillop, A.; Young, D. W. Synthesis 1979, 401, 481. Hojo, M. Yuki Gosei Kagaku Kyokaiski 1984, 42, 635. Cornelis, A.; Laszlo, P. Synthesis 1985, 909. Isobe, K.; Yagasaki, A. Acc. Chem. Res. 1993, 26, 524. Corma, A. Chem. Rev. 1995, 95, 559.
19. McKillop, A.; Young, D. W. Synthesis 1979, 401, 481. Hojo, M. Yuki Gosei Kagaku Kyokaiski 1984, 42, 635. Cornelis, A.; Laszlo, P. Synthesis 1985, 909. Isobe, K.; Yagasaki, A. Acc. Chem. Res. 1993, 26, 524. Corma, A. Chem. Rev. 1995, 95, 559.
20. McKillop, A.; Young, D. W. Synthesis 1979, 401, 481. Hojo, M. Yuki Gosei Kagaku Kyokaiski 1984, 42, 635. Cornelis, A.; Laszlo, P. Synthesis 1985, 909. Isobe, K.; Yagasaki, A. Acc. Chem. Res. 1993, 26, 524. Corma, A. Chem. Rev. 1995, 95, 559.
21. 2 as the solvent gave decreased yields.
22. Dauben, W. G.; Hendricks, R. T Tetrahedron Lett. 1992, 3, 603.
23. Jones, R. A.; Bean, G P. The Chemistry of Pyrroles; Academy Press: London, 1977. Lipshutz, B. H. Chem. Rev. 1986, 86, 795. For a general review see: Katritzky, A., Rees, C. W., Eds. Comprehensive Heterocyclic Chemistry; Pergamon Press: Oxford, 1984.
24. Jones, R. A.; Bean, G P. The Chemistry of Pyrroles; Academy Press: London, 1977. Lipshutz, B. H. Chem. Rev. 1986, 86, 795. For a general review see: Katritzky, A., Rees, C. W., Eds. Comprehensive Heterocyclic Chemistry; Pergamon Press: Oxford, 1984.
25. Jones, R. A.; Bean, G P. The Chemistry of Pyrroles; Academy Press: London, 1977. Lipshutz, B. H. Chem. Rev. 1986, 86, 795. For a general review see: Katritzky, A., Rees, C. W., Eds. Comprehensive Heterocyclic Chemistry; Pergamon Press: Oxford, 1984.
26. For example, see: Tanis, S. P.; Raggon, J. W. J. Org. Chem. 1987, 52, 819.
27. Due to the instability of pyrrole adducts, separation by TLC was best achieved at 0 °C.
28. For example, see: Hummer, W.; Gracza, T.; Jager, V. Tetrahedron Lett. 1989, 30, 1517. Murabayashi, A.; Makisumi, Y. Heterocycles 1990, 31, 537. Gala, D.; DiBenedetto, D. J. Tetrahedron Lett. 1994, 35, 8299. Bartroli, J.; Turmo, E.; Belloc, J.; Forn, J. J. Org. Chem. 1995, 60, 3000.
29. For example, see: Hummer, W.; Gracza, T.; Jager, V. Tetrahedron Lett. 1989, 30, 1517. Murabayashi, A.; Makisumi, Y. Heterocycles 1990, 31, 537. Gala, D.; DiBenedetto, D. J. Tetrahedron Lett. 1994, 35, 8299. Bartroli, J.; Turmo, E.; Belloc, J.; Forn, J. J. Org. Chem. 1995, 60, 3000.
30. For example, see: Hummer, W.; Gracza, T.; Jager, V. Tetrahedron Lett. 1989, 30, 1517. Murabayashi, A.; Makisumi, Y. Heterocycles 1990, 31, 537. Gala, D.; DiBenedetto, D. J. Tetrahedron Lett. 1994, 35, 8299. Bartroli, J.; Turmo, E.; Belloc, J.; Forn, J. J. Org. Chem. 1995, 60, 3000.
31. For example, see: Hummer, W.; Gracza, T.; Jager, V. Tetrahedron Lett. 1989, 30, 1517. Murabayashi, A.; Makisumi, Y. Heterocycles 1990, 31, 537. Gala, D.; DiBenedetto, D. J. Tetrahedron Lett. 1994, 35, 8299. Bartroli, J.; Turmo, E.; Belloc, J.; Forn, J. J. Org. Chem. 1995, 60, 3000.
32. Harris, C. E.; Fisher, G. B.; Beardsley, D.; Lee, L.; Goralski, C T.; Nicholson, L. W.; Singaram, B. J. Org. Chem. 1994, 59, 7746 and references cited therein.
33. 2 as the solvent for high-pressure reactions gave generally complex mixtures of products.
34. The benzene analogs such as benzimidazole were unreactive under these conditions.
35. le Noble, W. J. Prog. Phys. Org. Chem. 1967, 5, 207. Asano, T., le Noble, W. J. Chem. Rev. 1978, 78, 407. le Noble, W. J., Asano, T.; van Eldik, R. Ibid. 1989, 89, 549
36. le Noble, W. J. Prog. Phys. Org. Chem. 1967, 5, 207. Asano, T., le Noble, W. J. Chem. Rev. 1978, 78, 407. le Noble, W. J., Asano, T.; van Eldik, R. Ibid. 1989, 89, 549
37. le Noble, W. J. Prog. Phys. Org. Chem. 1967, 5, 207. Asano, T., le Noble, W. J. Chem. Rev. 1978, 78, 407. le Noble, W. J., Asano, T.; van Eldik, R. Ibid. 1989, 89, 549
38. 3). Prepared from diol 40 according to the literature procedure: Kim, S.; Chang, H. Bull. Chem. Soc. Jpn. 1985, 58, 3669. Mai, K.; Patil, G. J. Org. Chem. 1986, 51, 3545. Yamamoto, K.; Takemae, M. Bull. Chem. Soc. Jpn. 1989, 62, 2111. Leigh, D. A.; Martin, R. P.; Smart, J. P.; Truscello, A. M. J. Chem. Soc., Chem. Commun. 1994, 1373.
39. 3). Prepared from diol 40 according to the literature procedure: Kim, S.; Chang, H. Bull. Chem. Soc. Jpn. 1985, 58, 3669. Mai, K.; Patil, G. J. Org. Chem. 1986, 51, 3545. Yamamoto, K.; Takemae, M. Bull. Chem. Soc. Jpn. 1989, 62, 2111. Leigh, D. A.; Martin, R. P.; Smart, J. P.; Truscello, A. M. J. Chem. Soc., Chem. Commun. 1994, 1373.
40. 3). Prepared from diol 40 according to the literature procedure: Kim, S.; Chang, H. Bull. Chem. Soc. Jpn. 1985, 58, 3669. Mai, K.; Patil, G. J. Org. Chem. 1986, 51, 3545. Yamamoto, K.; Takemae, M. Bull. Chem. Soc. Jpn. 1989, 62, 2111. Leigh, D. A.; Martin, R. P.; Smart, J. P.; Truscello, A. M. J. Chem. Soc., Chem. Commun. 1994, 1373.
41. 3). Prepared from diol 40 according to the literature procedure: Kim, S.; Chang, H. Bull. Chem. Soc. Jpn. 1985, 58, 3669. Mai, K.; Patil, G. J. Org. Chem. 1986, 51, 3545. Yamamoto, K.; Takemae, M. Bull. Chem. Soc. Jpn. 1989, 62, 2111. Leigh, D. A.; Martin, R. P.; Smart, J. P.; Truscello, A. M. J. Chem. Soc., Chem. Commun. 1994, 1373.
42. Heath-Brown, B.; Philpott, P. G. J. Chem. Soc. 1965, 7165.
43. For a similar discussion, see: Biggs, J.; Chapman, N. B.; Wray, V. J. Chem. Soc. B 1971, 71. Lin, B.; Whalen, D. L. J. Org. Chem. 1994, 59, 1638. Boaz, N. W. Tetrahedron: Asymmetry 1995, 6, 15.
44. For a similar discussion, see: Biggs, J.; Chapman, N. B.; Wray, V. J. Chem. Soc. B 1971, 71. Lin, B.; Whalen, D. L. J. Org. Chem. 1994, 59, 1638. Boaz, N. W. Tetrahedron: Asymmetry 1995, 6, 15.
45. For a similar discussion, see: Biggs, J.; Chapman, N. B.; Wray, V. J. Chem. Soc. B 1971, 71. Lin, B.; Whalen, D. L. J. Org. Chem. 1994, 59, 1638. Boaz, N. W. Tetrahedron: Asymmetry 1995, 6, 15.
46. For a successful application to catalytic asymmetric synthesis, see: Kotsuki, H.; Hayakawa, H.; Wakao, M.; Shimanouchi, T.; Ochi, M. Tetrahedron: Asymmetry 1995, 6, 2665.
47. Kotsuki, H.; Nishikawa, H.; Mori, Y.; Ochi, M. J. Org. Chem. 1992, 57, 5036.
48. Cooper, G.; Irwin, W. J. J. Chem. Soc., Perkin Trans. 1 1976, 545.
49. Manley, P. W.; Lai, M. F. Eur. Pat. Appl. EP 105,575, 1984; Chem. Abstr. 1984, 101, 72725s.
50. Murabayashi, A.; Makisumi, Y. Heterocycles 1990, 31, 537.
51. Banfi, A.; Benedini, F.; Sala, A. J. Heterocycl. Chem. 1991, 28, 401.
52. Butler, D. E.; Alexander, S. M. J. Org. Chem. 1972, 37, 215.