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Volumn 65, Issue 5, 2000, Pages 1516-1524

An investigation of imidazole and oxazole syntheses using aryl- substituted TosMIC reagents

Author keywords

[No Author keywords available]

Indexed keywords

IMIDAZOLE DERIVATIVE; OXAZOLE DERIVATIVE;

EID: 0034629166     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991782l     Document Type: Article
Times cited : (171)

References (58)
  • 1
    • 85069412408 scopus 로고    scopus 로고
    • This paper is dedicated to the memory of our colleagues Ken Tubman and Lendon Pridgen, deceased August 1, 1999
    • This paper is dedicated to the memory of our colleagues Ken Tubman and Lendon Pridgen, deceased August 1, 1999.
  • 2
    • 77956796530 scopus 로고
    • For examples, see: Greenlee, W. J.; Siegl, P. K. S. Annu. Rep. Med. Chem. 1982, 27, 59. Hodges, J. C.; Hamby, J. M.; Blankley, C. J. Drugs Future 1992, 17, 575. Shilcrat, S. C.; Mokhallalati, M. K.; Fortunak, J. M. D.; Pridgen, L. N. J. Org. Chem. 1997, 62, 8449. Meanwell, N. A.; Romine, J. L.; Seiler, S. M. Drugs Future 1994, 19, 361. Rizzi, J. P.; Nagel, A. A.; Rosen, T.; McLEan, S.; Seeger, T. J. Med. Chem. 1990, 33, 2721. Shapiro, G.; Gomez-Lor, B. J. Org. Chem. 1994, 59, 5524. Adams, J. L.; Boehm, J. C.; Kassis, S.; Gorycki, P. D.; Webb, E. F.; Hall, R.; Sorenson, M.; Lee, J. C.; Ayrton, A.; Griswold, D. E.; Gallagher, T. F. Bioorg. Med. Chem. Lett. 1998, 8, 3111.
    • (1982) Annu. Rep. Med. Chem. , vol.27 , pp. 59
    • Greenlee, W.J.1    Siegl, P.K.S.2
  • 3
    • 0026688145 scopus 로고
    • For examples, see: Greenlee, W. J.; Siegl, P. K. S. Annu. Rep. Med. Chem. 1982, 27, 59. Hodges, J. C.; Hamby, J. M.; Blankley, C. J. Drugs Future 1992, 17, 575. Shilcrat, S. C.; Mokhallalati, M. K.; Fortunak, J. M. D.; Pridgen, L. N. J. Org. Chem. 1997, 62, 8449. Meanwell, N. A.; Romine, J. L.; Seiler, S. M. Drugs Future 1994, 19, 361. Rizzi, J. P.; Nagel, A. A.; Rosen, T.; McLEan, S.; Seeger, T. J. Med. Chem. 1990, 33, 2721. Shapiro, G.; Gomez-Lor, B. J. Org. Chem. 1994, 59, 5524. Adams, J. L.; Boehm, J. C.; Kassis, S.; Gorycki, P. D.; Webb, E. F.; Hall, R.; Sorenson, M.; Lee, J. C.; Ayrton, A.; Griswold, D. E.; Gallagher, T. F. Bioorg. Med. Chem. Lett. 1998, 8, 3111.
    • (1992) Drugs Future , vol.17 , pp. 575
    • Hodges, J.C.1    Hamby, J.M.2    Blankley, C.J.3
  • 4
    • 0001656259 scopus 로고    scopus 로고
    • For examples, see: Greenlee, W. J.; Siegl, P. K. S. Annu. Rep. Med. Chem. 1982, 27, 59. Hodges, J. C.; Hamby, J. M.; Blankley, C. J. Drugs Future 1992, 17, 575. Shilcrat, S. C.; Mokhallalati, M. K.; Fortunak, J. M. D.; Pridgen, L. N. J. Org. Chem. 1997, 62, 8449. Meanwell, N. A.; Romine, J. L.; Seiler, S. M. Drugs Future 1994, 19, 361. Rizzi, J. P.; Nagel, A. A.; Rosen, T.; McLEan, S.; Seeger, T. J. Med. Chem. 1990, 33, 2721. Shapiro, G.; Gomez-Lor, B. J. Org. Chem. 1994, 59, 5524. Adams, J. L.; Boehm, J. C.; Kassis, S.; Gorycki, P. D.; Webb, E. F.; Hall, R.; Sorenson, M.; Lee, J. C.; Ayrton, A.; Griswold, D. E.; Gallagher, T. F. Bioorg. Med. Chem. Lett. 1998, 8, 3111.
    • (1997) J. Org. Chem. , vol.62 , pp. 8449
    • Shilcrat, S.C.1    Mokhallalati, M.K.2    Fortunak, J.M.D.3    Pridgen, L.N.4
  • 5
    • 0028306705 scopus 로고
    • For examples, see: Greenlee, W. J.; Siegl, P. K. S. Annu. Rep. Med. Chem. 1982, 27, 59. Hodges, J. C.; Hamby, J. M.; Blankley, C. J. Drugs Future 1992, 17, 575. Shilcrat, S. C.; Mokhallalati, M. K.; Fortunak, J. M. D.; Pridgen, L. N. J. Org. Chem. 1997, 62, 8449. Meanwell, N. A.; Romine, J. L.; Seiler, S. M. Drugs Future 1994, 19, 361. Rizzi, J. P.; Nagel, A. A.; Rosen, T.; McLEan, S.; Seeger, T. J. Med. Chem. 1990, 33, 2721. Shapiro, G.; Gomez-Lor, B. J. Org. Chem. 1994, 59, 5524. Adams, J. L.; Boehm, J. C.; Kassis, S.; Gorycki, P. D.; Webb, E. F.; Hall, R.; Sorenson, M.; Lee, J. C.; Ayrton, A.; Griswold, D. E.; Gallagher, T. F. Bioorg. Med. Chem. Lett. 1998, 8, 3111.
    • (1994) Drugs Future , vol.19 , pp. 361
    • Meanwell, N.A.1    Romine, J.L.2    Seiler, S.M.3
  • 6
    • 0025102718 scopus 로고
    • For examples, see: Greenlee, W. J.; Siegl, P. K. S. Annu. Rep. Med. Chem. 1982, 27, 59. Hodges, J. C.; Hamby, J. M.; Blankley, C. J. Drugs Future 1992, 17, 575. Shilcrat, S. C.; Mokhallalati, M. K.; Fortunak, J. M. D.; Pridgen, L. N. J. Org. Chem. 1997, 62, 8449. Meanwell, N. A.; Romine, J. L.; Seiler, S. M. Drugs Future 1994, 19, 361. Rizzi, J. P.; Nagel, A. A.; Rosen, T.; McLEan, S.; Seeger, T. J. Med. Chem. 1990, 33, 2721. Shapiro, G.; Gomez-Lor, B. J. Org. Chem. 1994, 59, 5524. Adams, J. L.; Boehm, J. C.; Kassis, S.; Gorycki, P. D.; Webb, E. F.; Hall, R.; Sorenson, M.; Lee, J. C.; Ayrton, A.; Griswold, D. E.; Gallagher, T. F. Bioorg. Med. Chem. Lett. 1998, 8, 3111.
    • (1990) J. Med. Chem. , vol.33 , pp. 2721
    • Rizzi, J.P.1    Nagel, A.A.2    Rosen, T.3    McLean, S.4    Seeger, T.5
  • 7
    • 0027992835 scopus 로고
    • For examples, see: Greenlee, W. J.; Siegl, P. K. S. Annu. Rep. Med. Chem. 1982, 27, 59. Hodges, J. C.; Hamby, J. M.; Blankley, C. J. Drugs Future 1992, 17, 575. Shilcrat, S. C.; Mokhallalati, M. K.; Fortunak, J. M. D.; Pridgen, L. N. J. Org. Chem. 1997, 62, 8449. Meanwell, N. A.; Romine, J. L.; Seiler, S. M. Drugs Future 1994, 19, 361. Rizzi, J. P.; Nagel, A. A.; Rosen, T.; McLEan, S.; Seeger, T. J. Med. Chem. 1990, 33, 2721. Shapiro, G.; Gomez-Lor, B. J. Org. Chem. 1994, 59, 5524. Adams, J. L.; Boehm, J. C.; Kassis, S.; Gorycki, P. D.; Webb, E. F.; Hall, R.; Sorenson, M.; Lee, J. C.; Ayrton, A.; Griswold, D. E.; Gallagher, T. F. Bioorg. Med. Chem. Lett. 1998, 8, 3111.
    • (1994) J. Org. Chem. , vol.59 , pp. 5524
    • Shapiro, G.1    Gomez-Lor, B.2
  • 8
    • 0032541986 scopus 로고    scopus 로고
    • For examples, see: Greenlee, W. J.; Siegl, P. K. S. Annu. Rep. Med. Chem. 1982, 27, 59. Hodges, J. C.; Hamby, J. M.; Blankley, C. J. Drugs Future 1992, 17, 575. Shilcrat, S. C.; Mokhallalati, M. K.; Fortunak, J. M. D.; Pridgen, L. N. J. Org. Chem. 1997, 62, 8449. Meanwell, N. A.; Romine, J. L.; Seiler, S. M. Drugs Future 1994, 19, 361. Rizzi, J. P.; Nagel, A. A.; Rosen, T.; McLEan, S.; Seeger, T. J. Med. Chem. 1990, 33, 2721. Shapiro, G.; Gomez-Lor, B. J. Org. Chem. 1994, 59, 5524. Adams, J. L.; Boehm, J. C.; Kassis, S.; Gorycki, P. D.; Webb, E. F.; Hall, R.; Sorenson, M.; Lee, J. C.; Ayrton, A.; Griswold, D. E.; Gallagher, T. F. Bioorg. Med. Chem. Lett. 1998, 8, 3111.
    • (1998) Bioorg. Med. Chem. Lett. , vol.8 , pp. 3111
    • Adams, J.L.1    Boehm, J.C.2    Kassis, S.3    Gorycki, P.D.4    Webb, E.F.5    Hall, R.6    Sorenson, M.7    Lee, J.C.8    Ayrton, A.9    Griswold, D.E.10    Gallagher, T.F.11
  • 9
    • 0343417880 scopus 로고
    • Hetarene III/Teil 3; Schaumann, E., Ed.; Georg Thieme Verlag: Stuttgart
    • For imidazole syntheses, see: Ebel, K. In Methoden der Organischen Chemie (Houben-Weyl); Band E8c, Hetarene III/Teil 3; Schaumann, E., Ed.; Georg Thieme Verlag: Stuttgart, 1994; pp 1-215. Grimmett, M. R. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Boulton, A. J., Eds.; Academic: New York, 1980; Vol. 27, p 241. Grimmett, M. R. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Boulton, A. J., Eds.; Academic: New York, 1970; Vol. 12, p 103. See also, Reiter, L. A. J. Org. Chem. 1987, 52, 2714. Lantos, I.; Zhang, W. Y.; Shui, X.; Eggleston, D. S. J. Org. Chem. 1993, 58, 7092. Nunami, K.; Yamada, M.; Fukui, T.; Matsumoto, K. J. Org. Chem. 1994, 59, 7635. Hunt, J. T.; Bartlett, P. A. Synthesis 1978, 741.
    • (1994) Methoden der Organischen Chemie (Houben-Weyl) , vol.E8C , pp. 1-215
    • Ebel, K.1
  • 10
    • 0000045974 scopus 로고
    • Katritzky, A. R., Boulton, A. J., Eds.; Academic: New York
    • For imidazole syntheses, see: Ebel, K. In Methoden der Organischen Chemie (Houben-Weyl); Band E8c, Hetarene III/Teil 3; Schaumann, E., Ed.; Georg Thieme Verlag: Stuttgart, 1994; pp 1-215. Grimmett, M. R. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Boulton, A. J., Eds.; Academic: New York, 1980; Vol. 27, p 241. Grimmett, M. R. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Boulton, A. J., Eds.; Academic: New York, 1970; Vol. 12, p 103. See also, Reiter, L. A. J. Org. Chem. 1987, 52, 2714. Lantos, I.; Zhang, W. Y.; Shui, X.; Eggleston, D. S. J. Org. Chem. 1993, 58, 7092. Nunami, K.; Yamada, M.; Fukui, T.; Matsumoto, K. J. Org. Chem. 1994, 59, 7635. Hunt, J. T.; Bartlett, P. A. Synthesis 1978, 741.
    • (1980) Advances in Heterocyclic Chemistry , vol.27 , pp. 241
    • Grimmett, M.R.1
  • 11
    • 33646821630 scopus 로고
    • Katritzky, A. R., Boulton, A. J., Eds.; Academic: New York
    • For imidazole syntheses, see: Ebel, K. In Methoden der Organischen Chemie (Houben-Weyl); Band E8c, Hetarene III/Teil 3; Schaumann, E., Ed.; Georg Thieme Verlag: Stuttgart, 1994; pp 1-215. Grimmett, M. R. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Boulton, A. J., Eds.; Academic: New York, 1980; Vol. 27, p 241. Grimmett, M. R. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Boulton, A. J., Eds.; Academic: New York, 1970; Vol. 12, p 103. See also, Reiter, L. A. J. Org. Chem. 1987, 52, 2714. Lantos, I.; Zhang, W. Y.; Shui, X.; Eggleston, D. S. J. Org. Chem. 1993, 58, 7092. Nunami, K.; Yamada, M.; Fukui, T.; Matsumoto, K. J. Org. Chem. 1994, 59, 7635. Hunt, J. T.; Bartlett, P. A. Synthesis 1978, 741.
    • (1970) Advances in Heterocyclic Chemistry , vol.12 , pp. 103
    • Grimmett, M.R.1
  • 12
    • 0001300081 scopus 로고
    • For imidazole syntheses, see: Ebel, K. In Methoden der Organischen Chemie (Houben-Weyl); Band E8c, Hetarene III/Teil 3; Schaumann, E., Ed.; Georg Thieme Verlag: Stuttgart, 1994; pp 1-215. Grimmett, M. R. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Boulton, A. J., Eds.; Academic: New York, 1980; Vol. 27, p 241. Grimmett, M. R. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Boulton, A. J., Eds.; Academic: New York, 1970; Vol. 12, p 103. See also, Reiter, L. A. J. Org. Chem. 1987, 52, 2714. Lantos, I.; Zhang, W. Y.; Shui, X.; Eggleston, D. S. J. Org. Chem. 1993, 58, 7092. Nunami, K.; Yamada, M.; Fukui, T.; Matsumoto, K. J. Org. Chem. 1994, 59, 7635. Hunt, J. T.; Bartlett, P. A. Synthesis 1978, 741.
    • (1987) J. Org. Chem. , vol.52 , pp. 2714
    • Reiter, L.A.1
  • 13
    • 0027716078 scopus 로고
    • For imidazole syntheses, see: Ebel, K. In Methoden der Organischen Chemie (Houben-Weyl); Band E8c, Hetarene III/Teil 3; Schaumann, E., Ed.; Georg Thieme Verlag: Stuttgart, 1994; pp 1-215. Grimmett, M. R. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Boulton, A. J., Eds.; Academic: New York, 1980; Vol. 27, p 241. Grimmett, M. R. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Boulton, A. J., Eds.; Academic: New York, 1970; Vol. 12, p 103. See also, Reiter, L. A. J. Org. Chem. 1987, 52, 2714. Lantos, I.; Zhang, W. Y.; Shui, X.; Eggleston, D. S. J. Org. Chem. 1993, 58, 7092. Nunami, K.; Yamada, M.; Fukui, T.; Matsumoto, K. J. Org. Chem. 1994, 59, 7635. Hunt, J. T.; Bartlett, P. A. Synthesis 1978, 741.
    • (1993) J. Org. Chem. , vol.58 , pp. 7092
    • Lantos, I.1    Zhang, W.Y.2    Shui, X.3    Eggleston, D.S.4
  • 14
    • 0028569130 scopus 로고
    • For imidazole syntheses, see: Ebel, K. In Methoden der Organischen Chemie (Houben-Weyl); Band E8c, Hetarene III/Teil 3; Schaumann, E., Ed.; Georg Thieme Verlag: Stuttgart, 1994; pp 1-215. Grimmett, M. R. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Boulton, A. J., Eds.; Academic: New York, 1980; Vol. 27, p 241. Grimmett, M. R. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Boulton, A. J., Eds.; Academic: New York, 1970; Vol. 12, p 103. See also, Reiter, L. A. J. Org. Chem. 1987, 52, 2714. Lantos, I.; Zhang, W. Y.; Shui, X.; Eggleston, D. S. J. Org. Chem. 1993, 58, 7092. Nunami, K.; Yamada, M.; Fukui, T.; Matsumoto, K. J. Org. Chem. 1994, 59, 7635. Hunt, J. T.; Bartlett, P. A. Synthesis 1978, 741.
    • (1994) J. Org. Chem. , vol.59 , pp. 7635
    • Nunami, K.1    Yamada, M.2    Fukui, T.3    Matsumoto, K.4
  • 15
    • 0041867480 scopus 로고
    • For imidazole syntheses, see: Ebel, K. In Methoden der Organischen Chemie (Houben-Weyl); Band E8c, Hetarene III/Teil 3; Schaumann, E., Ed.; Georg Thieme Verlag: Stuttgart, 1994; pp 1-215. Grimmett, M. R. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Boulton, A. J., Eds.; Academic: New York, 1980; Vol. 27, p 241. Grimmett, M. R. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Boulton, A. J., Eds.; Academic: New York, 1970; Vol. 12, p 103. See also, Reiter, L. A. J. Org. Chem. 1987, 52, 2714. Lantos, I.; Zhang, W. Y.; Shui, X.; Eggleston, D. S. J. Org. Chem. 1993, 58, 7092. Nunami, K.; Yamada, M.; Fukui, T.; Matsumoto, K. J. Org. Chem. 1994, 59, 7635. Hunt, J. T.; Bartlett, P. A. Synthesis 1978, 741.
    • (1978) Synthesis , pp. 741
    • Hunt, J.T.1    Bartlett, P.A.2
  • 17
    • 0000894948 scopus 로고
    • van Leusen, A. M.; Wildeman, J.; Oldenziel, O. H. J. Org. Chem. 1977, 42, 1153. van Leusen, A. M. Lect. Heterocycl. Chem. 1980, 5, S-111.
    • (1980) Lect. Heterocycl. Chem. , vol.5
    • Van Leusen, A.M.1
  • 24
    • 85069416839 scopus 로고    scopus 로고
    • note
    • 3 in MeOH). However, fairly subtle stereoelectronic effects seem to govern the outcome of these reactions. For example, C,N-diaryl- and C,N-dialykylimines react with TosMIC to give the corresponding imidazoles in good to excellent yields while C-aryl,N-alkylimines react poorly with TosMIC to give low yields of imidazole product (0-37%). In the only example of its kind reported, the methyl-substituted TosMIC reagent combines with a C,N-diarylimine to give the imidazole in 75% yield, but required the action of NaH in an aprotic solvent (DME).
  • 25
    • 0025830922 scopus 로고
    • Frannowski, A.; Seliga, C.; Bur, D.; Streith, J. Helv. Chim. Acta 1991, 74, 934. Nishi, T.; Higashi, K.; Soga, T.; Takemura, M.; Sato, M. J. Antibiot. 1994, 47, 357. Browne, L. J.; Gude, C.; Rodriguez, H.; Steele, R. E. J. Med. Chem. 1991, 34, 725. See also: Aldabbagh, F.; Bowman, W. R.; Mann, E. Tetrahedron Lett. 1997, 38, 7937.
    • (1991) Chim. Acta , vol.74 , pp. 934
    • Frannowski, A.1    Seliga, C.2    Bur, D.3    Helv, S.J.4
  • 26
    • 0028197643 scopus 로고
    • Frannowski, A.; Seliga, C.; Bur, D.; Streith, J. Helv. Chim. Acta 1991, 74, 934. Nishi, T.; Higashi, K.; Soga, T.; Takemura, M.; Sato, M. J. Antibiot. 1994, 47, 357. Browne, L. J.; Gude, C.; Rodriguez, H.; Steele, R. E. J. Med. Chem. 1991, 34, 725. See also: Aldabbagh, F.; Bowman, W. R.; Mann, E. Tetrahedron Lett. 1997, 38, 7937.
    • (1994) J. Antibiot. , vol.47 , pp. 357
    • Nishi, T.1    Higashi, K.2    Soga, T.3    Takemura, M.4    Sato, M.5
  • 27
    • 0025970208 scopus 로고
    • Frannowski, A.; Seliga, C.; Bur, D.; Streith, J. Helv. Chim. Acta 1991, 74, 934. Nishi, T.; Higashi, K.; Soga, T.; Takemura, M.; Sato, M. J. Antibiot. 1994, 47, 357. Browne, L. J.; Gude, C.; Rodriguez, H.; Steele, R. E. J. Med. Chem. 1991, 34, 725. See also: Aldabbagh, F.; Bowman, W. R.; Mann, E. Tetrahedron Lett. 1997, 38, 7937.
    • (1991) J. Med. Chem. , vol.34 , pp. 725
    • Browne, L.J.1    Gude, C.2    Rodriguez, H.3    Steele, R.E.4
  • 28
    • 0030840135 scopus 로고    scopus 로고
    • Frannowski, A.; Seliga, C.; Bur, D.; Streith, J. Helv. Chim. Acta 1991, 74, 934. Nishi, T.; Higashi, K.; Soga, T.; Takemura, M.; Sato, M. J. Antibiot. 1994, 47, 357. Browne, L. J.; Gude, C.; Rodriguez, H.; Steele, R. E. J. Med. Chem. 1991, 34, 725. See also: Aldabbagh, F.; Bowman, W. R.; Mann, E. Tetrahedron Lett. 1997, 38, 7937.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 7937
    • Aldabbagh, F.1    Bowman, W.R.2    Mann, E.3
  • 31
    • 85069412573 scopus 로고    scopus 로고
    • See ref 5 and references therein
    • See ref 5 and references therein.
  • 33
    • 0028948019 scopus 로고
    • Palkowitz, A. D.; Steinberg, M. I.; Thrasher, K. J.; Reel, J. K.; Hauser, K. L.; Zimmerman, K. M.; Wiest, S. A.; Whitesitt, C. A.; Simon, R. L.; Pfeifer, W.; Lifer, S. L.; Boyd, D. B.; Barnett, C. J.; Wilson, T. M.; Deeter, J. B.; Takeuchi, K.; Riley, R. E.; Miller, W. D.; Marshall, W. S. J. Med. Chem. 1994, 37, 4508. Zaderenko, P.; Lopez, P.; Ballesteros, P.; Takumi, H.; Toda, F. Tetrahedron: Asymmetry 1995, 6, 381. Zaderenko, P.; Lopez, M. C.; Ballesteros, P. J. Org. Chem. 1996, 61, 6825. Birkett, P. R.; King, H.; Chapleo, C. B.; Ewing, D. F.; Mackenzie, G. Tetrahedron 1993, 49, 11029. Messina, F.; Botta, M.; Corelli, F.; Schneider, M. P.; Fazio, F. J. Org. Chem. 1999, 64, 3767.
    • (1995) Tetrahedron: Asymmetry , vol.6 , pp. 381
    • Zaderenko, P.1    Lopez, P.2    Ballesteros, P.3    Takumi, H.4    Toda, F.5
  • 34
    • 0001095726 scopus 로고    scopus 로고
    • Palkowitz, A. D.; Steinberg, M. I.; Thrasher, K. J.; Reel, J. K.; Hauser, K. L.; Zimmerman, K. M.; Wiest, S. A.; Whitesitt, C. A.; Simon, R. L.; Pfeifer, W.; Lifer, S. L.; Boyd, D. B.; Barnett, C. J.; Wilson, T. M.; Deeter, J. B.; Takeuchi, K.; Riley, R. E.; Miller, W. D.; Marshall, W. S. J. Med. Chem. 1994, 37, 4508. Zaderenko, P.; Lopez, P.; Ballesteros, P.; Takumi, H.; Toda, F. Tetrahedron: Asymmetry 1995, 6, 381. Zaderenko, P.; Lopez, M. C.; Ballesteros, P. J. Org. Chem. 1996, 61, 6825. Birkett, P. R.; King, H.; Chapleo, C. B.; Ewing, D. F.; Mackenzie, G. Tetrahedron 1993, 49, 11029. Messina, F.; Botta, M.; Corelli, F.; Schneider, M. P.; Fazio, F. J. Org. Chem. 1999, 64, 3767.
    • (1996) J. Org. Chem. , vol.61 , pp. 6825
    • Zaderenko, P.1    Lopez, M.C.2    Ballesteros, P.3
  • 35
    • 0027519745 scopus 로고
    • Palkowitz, A. D.; Steinberg, M. I.; Thrasher, K. J.; Reel, J. K.; Hauser, K. L.; Zimmerman, K. M.; Wiest, S. A.; Whitesitt, C. A.; Simon, R. L.; Pfeifer, W.; Lifer, S. L.; Boyd, D. B.; Barnett, C. J.; Wilson, T. M.; Deeter, J. B.; Takeuchi, K.; Riley, R. E.; Miller, W. D.; Marshall, W. S. J. Med. Chem. 1994, 37, 4508. Zaderenko, P.; Lopez, P.; Ballesteros, P.; Takumi, H.; Toda, F. Tetrahedron: Asymmetry 1995, 6, 381. Zaderenko, P.; Lopez, M. C.; Ballesteros, P. J. Org. Chem. 1996, 61, 6825. Birkett, P. R.; King, H.; Chapleo, C. B.; Ewing, D. F.; Mackenzie, G. Tetrahedron 1993, 49, 11029. Messina, F.; Botta, M.; Corelli, F.; Schneider, M. P.; Fazio, F. J. Org. Chem. 1999, 64, 3767.
    • (1993) Tetrahedron , vol.49 , pp. 11029
    • Birkett, P.R.1    King, H.2    Chapleo, C.B.3    Ewing, D.F.4    Mackenzie, G.5
  • 36
    • 0032955888 scopus 로고    scopus 로고
    • Palkowitz, A. D.; Steinberg, M. I.; Thrasher, K. J.; Reel, J. K.; Hauser, K. L.; Zimmerman, K. M.; Wiest, S. A.; Whitesitt, C. A.; Simon, R. L.; Pfeifer, W.; Lifer, S. L.; Boyd, D. B.; Barnett, C. J.; Wilson, T. M.; Deeter, J. B.; Takeuchi, K.; Riley, R. E.; Miller, W. D.; Marshall, W. S. J. Med. Chem. 1994, 37, 4508. Zaderenko, P.; Lopez, P.; Ballesteros, P.; Takumi, H.; Toda, F. Tetrahedron: Asymmetry 1995, 6, 381. Zaderenko, P.; Lopez, M. C.; Ballesteros, P. J. Org. Chem. 1996, 61, 6825. Birkett, P. R.; King, H.; Chapleo, C. B.; Ewing, D. F.; Mackenzie, G. Tetrahedron 1993, 49, 11029. Messina, F.; Botta, M.; Corelli, F.; Schneider, M. P.; Fazio, F. J. Org. Chem. 1999, 64, 3767.
    • (1999) J. Org. Chem. , vol.64 , pp. 3767
    • Messina, F.1    Botta, M.2    Corelli, F.3    Schneider, M.P.4    Fazio, F.5
  • 38
    • 0037768402 scopus 로고
    • For the preparation of chiral amino aldehydes, see: Jurczak, J.; Golebiowski, A. Chem. Rev. 1989, 89, 149. McNulty, J.; Still, I. W. Synth. Commun. 1992, 22, 979. Fehrentz, J.-A.; Castro, B. Synthesis 1983, 676.
    • (1989) Chem. Rev. , vol.89 , pp. 149
    • Jurczak, J.1    Golebiowski, A.2
  • 39
    • 0026535065 scopus 로고
    • For the preparation of chiral amino aldehydes, see: Jurczak, J.; Golebiowski, A. Chem. Rev. 1989, 89, 149. McNulty, J.; Still, I. W. Synth. Commun. 1992, 22, 979. Fehrentz, J.-A.; Castro, B. Synthesis 1983, 676.
    • (1992) Synth. Commun. , vol.22 , pp. 979
    • McNulty, J.1    Still, I.W.2
  • 40
    • 85004872164 scopus 로고
    • For the preparation of chiral amino aldehydes, see: Jurczak, J.; Golebiowski, A. Chem. Rev. 1989, 89, 149. McNulty, J.; Still, I. W. Synth. Commun. 1992, 22, 979. Fehrentz, J.-A.; Castro, B. Synthesis 1983, 676.
    • (1983) Synthesis , pp. 676
    • Fehrentz, J.-A.1    Castro, B.2
  • 41
    • 84980270929 scopus 로고
    • Pyruvaldehyde is known to decompose under certain conditions to give formaldehyde, see: Tyndall, G. S.; Staffelbach, T. A.; Orlando, J. J.; Calvert, J. G. Int. J. Chem. Kinet. 1995, 27, 1009. An alternative explanation would involve deacylation of imine 39 to give formaldimine 42 directly.
    • (1995) Int. J. Chem. Kinet. , vol.27 , pp. 1009
    • Tyndall, G.S.1    Staffelbach, T.A.2    Orlando, J.J.3    Calvert, J.G.4
  • 42
    • 43949157356 scopus 로고
    • A similar sequence has been proposed by Buchi et al., to account for the formation of imidazoles from the reaction of amines with tosyloxazolines similar to 43. However, they apparently were unable to isolate intermediates similar to 44. See: Horne, D. A.; Yakushijin, K.; Büchi, G. Heterocycles 1994, 39, 139.
    • (1994) Heterocycles , vol.39 , pp. 139
    • Horne, D.A.1    Yakushijin, K.2    Büchi, G.3
  • 44
    • 0030749151 scopus 로고    scopus 로고
    • ten Have, R.; Huisman, M.; Meetsma, A.; van Leusen, A. M. Tetrahederon 1997, 53, 11355. For another possible alternative method, see: van Leusen, A. M.; Schaart, F. J.; van Leusen, D. Rec. Trav. Chim. Pays-Bas 1979, 98, 258.
    • (1997) Tetrahederon , vol.53 , pp. 11355
    • Ten Have, R.1    Huisman, M.2    Meetsma, A.3    Van Leusen, A.M.4
  • 50
    • 0032474876 scopus 로고    scopus 로고
    • Larter, M. L.; Phillips, M.; Ortega, F.; Aguirre, G.; Somanathan, R.; Walsh, P. J. Tetrahedron Lett. 1998, 39, 4785. Hunter, D. H.; Kim, S. K. Can. J. Chem. 1972, 50, 669.
    • (1972) Can. J. Chem. , vol.50 , pp. 669
    • Hunter, D.H.1    Kim, S.K.2
  • 53
    • 0002565141 scopus 로고
    • Possel, O.; van Leusen, A. M. Heterocycles 1977, 7, 77. Saikachi, H.; Kitagawa, T.; Sasaki, H.; van Leusen, A. M. Chem. Pharm. Bull. 1979, 27, 793. Hiemstra, H.; Houwing, H. A.; Possel, O., van Leusen, A. M. Can. J. Chem. 1979, 57, 3168.
    • (1977) Heterocycles , vol.7 , pp. 77
    • Possel, O.1    Van Leusen, A.M.2
  • 54
    • 0018419770 scopus 로고
    • Possel, O.; van Leusen, A. M. Heterocycles 1977, 7, 77. Saikachi, H.; Kitagawa, T.; Sasaki, H.; van Leusen, A. M. Chem. Pharm. Bull. 1979, 27, 793. Hiemstra, H.; Houwing, H. A.; Possel, O., van Leusen, A. M. Can. J. Chem. 1979, 57, 3168.
    • (1979) Chem. Pharm. Bull. , vol.27 , pp. 793
    • Saikachi, H.1    Kitagawa, T.2    Sasaki, H.3    Van Leusen, A.M.4
  • 55
    • 0242709133 scopus 로고
    • Possel, O.; van Leusen, A. M. Heterocycles 1977, 7, 77. Saikachi, H.; Kitagawa, T.; Sasaki, H.; van Leusen, A. M. Chem. Pharm. Bull. 1979, 27, 793. Hiemstra, H.; Houwing, H. A.; Possel, O., van Leusen, A. M. Can. J. Chem. 1979, 57, 3168.
    • (1979) Can. J. Chem. , vol.57 , pp. 3168
    • Hiemstra, H.1    Houwing, H.A.2    Possel, O.3    Van Leusen, A.M.4
  • 57
    • 84986764181 scopus 로고
    • See Eicher, T.; Hauptmann, S. The Chemistry of Heterocycles; Thieme: Stuttgart, 1995; p. 167. Papadopoulos, E. P.; Hollstein, U. Org. Magn. Reson. 1982, 19, 188.
    • (1982) Org. Magn. Reson. , vol.19 , pp. 188
    • Papadopoulos, E.P.1    Hollstein, U.2


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