A new pathway to substituted 6-chloro-2-pyridinecarboxylic acid derivatives from the reaction of 4,6-dichloro-2-oxa-5-azabicyclo[2.2.2]oct-5-en-3-ones with nucleophiles

Tetrahedron

Volumn 52, Issue 20, 1996, Pages 6997-7002

  Dubois, Kristof J ^a   Hoornaert, Georges J ^a  

^a UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

PYRIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0029918044     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00304-3     Document Type: Article

References (21)

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2. Ogino, H.; Iwamatsu, K.; Katano, K.; Nakabayashi, S.; Yoshida, T.; Tsuruoka, T.; Inouye, S.; Kondo, S. J. Antibiotics 1990, 43, 2, 174-188; Rao, K.V.; Venkateswarlu, P. J. Heterocycl. Chem. 1975, 731-735; Blank, B.; Ditullio, N.W.; Miao, C.K.; Owings, F.F.; Gleason, J.G.; Ross, S.T.; Berkoff, C.E.; Saunders, H.L. J. Med Chem. 1974, 17, 10, 1065-1071; Kiener, A. Angew. Chem. 1992, 104, 748-749.
3. Ogino, H.; Iwamatsu, K.; Katano, K.; Nakabayashi, S.; Yoshida, T.; Tsuruoka, T.; Inouye, S.; Kondo, S. J. Antibiotics 1990, 43, 2, 174-188; Rao, K.V.; Venkateswarlu, P. J. Heterocycl. Chem. 1975, 731-735; Blank, B.; Ditullio, N.W.; Miao, C.K.; Owings, F.F.; Gleason, J.G.; Ross, S.T.; Berkoff, C.E.; Saunders, H.L. J. Med Chem. 1974, 17, 10, 1065-1071; Kiener, A. Angew. Chem. 1992, 104, 748-749.
4. Ogino, H.; Iwamatsu, K.; Katano, K.; Nakabayashi, S.; Yoshida, T.; Tsuruoka, T.; Inouye, S.; Kondo, S. J. Antibiotics 1990, 43, 2, 174-188; Rao, K.V.; Venkateswarlu, P. J. Heterocycl. Chem. 1975, 731-735; Blank, B.; Ditullio, N.W.; Miao, C.K.; Owings, F.F.; Gleason, J.G.; Ross, S.T.; Berkoff, C.E.; Saunders, H.L. J. Med Chem. 1974, 17, 10, 1065-1071; Kiener, A. Angew. Chem. 1992, 104, 748-749.
5. See, for recent examples: Makino, E.; Iwasaki, N.; Yagi, N.; Ohashi, T.; Kato, H.; Ito, Y.; Azuma, H. Chem. Pharm. Bull. 1990, 38, 201-207. Foster, C.J.; Gilkerson, T.; Stocker, R. European Patent # 447,004 (Chem. Abstr. 1992, 116, 128668e). Finkelstein, B.L., US Patent # 794,554 (Chem. Abstr. 1993, 119, 160130w). Takasugi, H.; Kuno, A.; Sakai, H. European Patent # 387,070 (Chem. Abstr. 1991, 114, P101743x). Takabe, F.; Saito, Y.; Tamaru, M.; Tachikawa, S.; Yoshida, R. Japanese Patent # 06,316,574 (Chem. Abstr. 1995, 122, 160668e). Kleemann, A.; Graef, H. British Patent # 2,277,930 (Chem. Abstr. 1995, 122, 105924).
6. See, for recent examples: Makino, E.; Iwasaki, N.; Yagi, N.; Ohashi, T.; Kato, H.; Ito, Y.; Azuma, H. Chem. Pharm. Bull. 1990, 38, 201-207. Foster, C.J.; Gilkerson, T.; Stocker, R. European Patent # 447,004 (Chem. Abstr. 1992, 116, 128668e). Finkelstein, B.L., US Patent # 794,554 (Chem. Abstr. 1993, 119, 160130w). Takasugi, H.; Kuno, A.; Sakai, H. European Patent # 387,070 (Chem. Abstr. 1991, 114, P101743x). Takabe, F.; Saito, Y.; Tamaru, M.; Tachikawa, S.; Yoshida, R. Japanese Patent # 06,316,574 (Chem. Abstr. 1995, 122, 160668e). Kleemann, A.; Graef, H. British Patent # 2,277,930 (Chem. Abstr. 1995, 122, 105924).
7. See, for recent examples: Makino, E.; Iwasaki, N.; Yagi, N.; Ohashi, T.; Kato, H.; Ito, Y.; Azuma, H. Chem. Pharm. Bull. 1990, 38, 201-207. Foster, C.J.; Gilkerson, T.; Stocker, R. European Patent # 447,004 (Chem. Abstr. 1992, 116, 128668e). Finkelstein, B.L., US Patent # 794,554 (Chem. Abstr. 1993, 119, 160130w). Takasugi, H.; Kuno, A.; Sakai, H. European Patent # 387,070 (Chem. Abstr. 1991, 114, P101743x). Takabe, F.; Saito, Y.; Tamaru, M.; Tachikawa, S.; Yoshida, R. Japanese Patent # 06,316,574 (Chem. Abstr. 1995, 122, 160668e). Kleemann, A.; Graef, H. British Patent # 2,277,930 (Chem. Abstr. 1995, 122, 105924).
8. See, for recent examples: Makino, E.; Iwasaki, N.; Yagi, N.; Ohashi, T.; Kato, H.; Ito, Y.; Azuma, H. Chem. Pharm. Bull. 1990, 38, 201-207. Foster, C.J.; Gilkerson, T.; Stocker, R. European Patent # 447,004 (Chem. Abstr. 1992, 116, 128668e). Finkelstein, B.L., US Patent # 794,554 (Chem. Abstr. 1993, 119, 160130w). Takasugi, H.; Kuno, A.; Sakai, H. European Patent # 387,070 (Chem. Abstr. 1991, 114, P101743x). Takabe, F.; Saito, Y.; Tamaru, M.; Tachikawa, S.; Yoshida, R. Japanese Patent # 06,316,574 (Chem. Abstr. 1995, 122, 160668e). Kleemann, A.; Graef, H. British Patent # 2,277,930 (Chem. Abstr. 1995, 122, 105924).
9. See, for recent examples: Makino, E.; Iwasaki, N.; Yagi, N.; Ohashi, T.; Kato, H.; Ito, Y.; Azuma, H. Chem. Pharm. Bull. 1990, 38, 201-207. Foster, C.J.; Gilkerson, T.; Stocker, R. European Patent # 447,004 (Chem. Abstr. 1992, 116, 128668e). Finkelstein, B.L., US Patent # 794,554 (Chem. Abstr. 1993, 119, 160130w). Takasugi, H.; Kuno, A.; Sakai, H. European Patent # 387,070 (Chem. Abstr. 1991, 114, P101743x). Takabe, F.; Saito, Y.; Tamaru, M.; Tachikawa, S.; Yoshida, R. Japanese Patent # 06,316,574 (Chem. Abstr. 1995, 122, 160668e). Kleemann, A.; Graef, H. British Patent # 2,277,930 (Chem. Abstr. 1995, 122, 105924).
10. See, for recent examples: Makino, E.; Iwasaki, N.; Yagi, N.; Ohashi, T.; Kato, H.; Ito, Y.; Azuma, H. Chem. Pharm. Bull. 1990, 38, 201-207. Foster, C.J.; Gilkerson, T.; Stocker, R. European Patent # 447,004 (Chem. Abstr. 1992, 116, 128668e). Finkelstein, B.L., US Patent # 794,554 (Chem. Abstr. 1993, 119, 160130w). Takasugi, H.; Kuno, A.; Sakai, H. European Patent # 387,070 (Chem. Abstr. 1991, 114, P101743x). Takabe, F.; Saito, Y.; Tamaru, M.; Tachikawa, S.; Yoshida, R. Japanese Patent # 06,316,574 (Chem. Abstr. 1995, 122, 160668e). Kleemann, A.; Graef, H. British Patent # 2,277,930 (Chem. Abstr. 1995, 122, 105924).
11. Dubois, K.; Fannes, C.; Compernolle, F.; Hoornaert, G. Tetrahedron 1996, in press.
12. Fannes, C.; Meerpoel, L.; Hoornaert, G. Synthesis, 1992, 705-709.
13. Meerpoel, L.; Hoornaert, G. Synthesis 1990, 905-908.
14. Cycloadducts 3 (except 3c,e) and their yields have been described in ref 4.
15. Kiener, A.; Glöckler, R.; Heinzmann, K. J. Chem. Soc. Perkin Trans 1 1993, 1201-1202. Yamamoto, Y.; Azuma, Y.; Mitoh, H. Synthesis 1986, 564-565. Yamamoto, Y.; Yamagi, A. Chem. Pharm. Bull. 1982, 30, 1731-1737; Yamamoto, Y.; Yamagi, A. Chem. Pharm. Bull. 1982, 30, 2003-2010; Kutsher, B.; Dieter, H.R.; Trömer, H.-G.; Bartz, B.; Engel, J.; Kleeman, A. Liebigs Ann. 1995, 591-592; Trécourt, F.; Mallet, M.; Mongin, O.; Quéguiner, G. J. Org. Chem. 1994, 59, 6173-6178.
16. Kiener, A.; Glöckler, R.; Heinzmann, K. J. Chem. Soc. Perkin Trans 1 1993, 1201-1202. Yamamoto, Y.; Azuma, Y.; Mitoh, H. Synthesis 1986, 564-565. Yamamoto, Y.; Yamagi, A. Chem. Pharm. Bull. 1982, 30, 1731-1737; Yamamoto, Y.; Yamagi, A. Chem. Pharm. Bull. 1982, 30, 2003-2010; Kutsher, B.; Dieter, H.R.; Trömer, H.-G.; Bartz, B.; Engel, J.; Kleeman, A. Liebigs Ann. 1995, 591-592; Trécourt, F.; Mallet, M.; Mongin, O.; Quéguiner, G. J. Org. Chem. 1994, 59, 6173-6178.
17. Kiener, A.; Glöckler, R.; Heinzmann, K. J. Chem. Soc. Perkin Trans 1 1993, 1201-1202. Yamamoto, Y.; Azuma, Y.; Mitoh, H. Synthesis 1986, 564-565. Yamamoto, Y.; Yamagi, A. Chem. Pharm. Bull. 1982, 30, 1731-1737; Yamamoto, Y.; Yamagi, A. Chem. Pharm. Bull. 1982, 30, 2003-2010; Kutsher, B.; Dieter, H.R.; Trömer, H.-G.; Bartz, B.; Engel, J.; Kleeman, A. Liebigs Ann. 1995, 591-592; Trécourt, F.; Mallet, M.; Mongin, O.; Quéguiner, G. J. Org. Chem. 1994, 59, 6173-6178.
18. Kiener, A.; Glöckler, R.; Heinzmann, K. J. Chem. Soc. Perkin Trans 1 1993, 1201-1202. Yamamoto, Y.; Azuma, Y.; Mitoh, H. Synthesis 1986, 564-565. Yamamoto, Y.; Yamagi, A. Chem. Pharm. Bull. 1982, 30, 1731-1737; Yamamoto, Y.; Yamagi, A. Chem. Pharm. Bull. 1982, 30, 2003-2010; Kutsher, B.; Dieter, H.R.; Trömer, H.-G.; Bartz, B.; Engel, J.; Kleeman, A. Liebigs Ann. 1995, 591-592; Trécourt, F.; Mallet, M.; Mongin, O.; Quéguiner, G. J. Org. Chem. 1994, 59, 6173-6178.
19. Kiener, A.; Glöckler, R.; Heinzmann, K. J. Chem. Soc. Perkin Trans 1 1993, 1201-1202. Yamamoto, Y.; Azuma, Y.; Mitoh, H. Synthesis 1986, 564-565. Yamamoto, Y.; Yamagi, A. Chem. Pharm. Bull. 1982, 30, 1731-1737; Yamamoto, Y.; Yamagi, A. Chem. Pharm. Bull. 1982, 30, 2003-2010; Kutsher, B.; Dieter, H.R.; Trömer, H.-G.; Bartz, B.; Engel, J.; Kleeman, A. Liebigs Ann. 1995, 591-592; Trécourt, F.; Mallet, M.; Mongin, O.; Quéguiner, G. J. Org. Chem. 1994, 59, 6173-6178.
20. Kiener, A.; Glöckler, R.; Heinzmann, K. J. Chem. Soc. Perkin Trans 1 1993, 1201-1202. Yamamoto, Y.; Azuma, Y.; Mitoh, H. Synthesis 1986, 564-565. Yamamoto, Y.; Yamagi, A. Chem. Pharm. Bull. 1982, 30, 1731-1737; Yamamoto, Y.; Yamagi, A. Chem. Pharm. Bull. 1982, 30, 2003-2010; Kutsher, B.; Dieter, H.R.; Trömer, H.-G.; Bartz, B.; Engel, J.; Kleeman, A. Liebigs Ann. 1995, 591-592; Trécourt, F.; Mallet, M.; Mongin, O.; Quéguiner, G. J. Org. Chem. 1994, 59, 6173-6178.
21. Kalinowski, H.; Berger, S.; Braun, S. In Carbon-13 NMR Spectroscopy, John Wiley and Sons: New York, 1988; p 526.