4,6-Dichloro-2-oxa-5-azabicyclo[2.2.2]oct-5-en-3-ones and their Use in the Synthesis of 1,6-Dihydro-6-Oxo-2-pyridine-and 6-Oxo-2-piperidinecarboxylates

Tetrahedron

Volumn 52, Issue 7, 1996, Pages 2591-2602

  Dubois, Kristof J ^a   Fannes, Christine C ^a   Compernolle, Frans ^a   Hoornaert, Georges J ^a  

^a UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

PYRIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030042070     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)01084-X     Document Type: Article

References (22)

1. See, for examples : Lesimple, P.; Bigg, D. Synthesis 1991, 306. Larchevêque, M.; Henrot, S. Tetrahedron, 1990, 46, 4277. Node, M.; Nishide, K.; Ochiai, M.; Fuji, K.; Fujita, E. J. Org. Chem., 1981, 46, 5163. Liotta, D.; Sunay, U.; Santiesteban, H.; Markiewicz, W. J. Org. Chem., 1981, 46, 2605. Basha, A.; Lipton, M.; Weinreb, S. M. Tetrahedron lett., 1977, 18, 4171.
2. See, for examples : Lesimple, P.; Bigg, D. Synthesis 1991, 306. Larchevêque, M.; Henrot, S. Tetrahedron, 1990, 46, 4277. Node, M.; Nishide, K.; Ochiai, M.; Fuji, K.; Fujita, E. J. Org. Chem., 1981, 46, 5163. Liotta, D.; Sunay, U.; Santiesteban, H.; Markiewicz, W. J. Org. Chem., 1981, 46, 2605. Basha, A.; Lipton, M.; Weinreb, S. M. Tetrahedron lett., 1977, 18, 4171.
3. See, for examples : Lesimple, P.; Bigg, D. Synthesis 1991, 306. Larchevêque, M.; Henrot, S. Tetrahedron, 1990, 46, 4277. Node, M.; Nishide, K.; Ochiai, M.; Fuji, K.; Fujita, E. J. Org. Chem., 1981, 46, 5163. Liotta, D.; Sunay, U.; Santiesteban, H.; Markiewicz, W. J. Org. Chem., 1981, 46, 2605. Basha, A.; Lipton, M.; Weinreb, S. M. Tetrahedron lett., 1977, 18, 4171.
4. See, for examples : Lesimple, P.; Bigg, D. Synthesis 1991, 306. Larchevêque, M.; Henrot, S. Tetrahedron, 1990, 46, 4277. Node, M.; Nishide, K.; Ochiai, M.; Fuji, K.; Fujita, E. J. Org. Chem., 1981, 46, 5163. Liotta, D.; Sunay, U.; Santiesteban, H.; Markiewicz, W. J. Org. Chem., 1981, 46, 2605. Basha, A.; Lipton, M.; Weinreb, S. M. Tetrahedron lett., 1977, 18, 4171.
5. See, for examples : Lesimple, P.; Bigg, D. Synthesis 1991, 306. Larchevêque, M.; Henrot, S. Tetrahedron, 1990, 46, 4277. Node, M.; Nishide, K.; Ochiai, M.; Fuji, K.; Fujita, E. J. Org. Chem., 1981, 46, 5163. Liotta, D.; Sunay, U.; Santiesteban, H.; Markiewicz, W. J. Org. Chem., 1981, 46, 2605. Basha, A.; Lipton, M.; Weinreb, S. M. Tetrahedron lett., 1977, 18, 4171.
6. Fannes, C.; Meerpoel, L.; Hoornaert, G. Synthesis, 1992, 705.
7. For the preparation of 1,6-dihydro-6-oxo-2-pyridinecarboxylic acid derivatives see, for examples: Katsuhiro, K.; Kimiko, H.; Harushisa, S.; Takeshi, M. Heterocycles 1986, 24, 2169-72; Van der Puy, M.; Nalewajek, D.; Wicks, G.E. Tetrahedron Lett. 1988, 29, 4389.
8. For the preparation of 1,6-dihydro-6-oxo-2-pyridinecarboxylic acid derivatives see, for examples: Katsuhiro, K.; Kimiko, H.; Harushisa, S.; Takeshi, M. Heterocycles 1986, 24, 2169-72; Van der Puy, M.; Nalewajek, D.; Wicks, G.E. Tetrahedron Lett. 1988, 29, 4389.
9. Yamano, K.; Shirahama, H. Chem. Lett. 1993, 21-24.
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14. Lee, D. L.; Rapoport, H. J. Org. Chem., 1975, 40, 3491. Boger, D. L.; Corbett, W. L.; Curran, T. T.; Kasper, A. M. J. Am. Chem. Soc., 1991, 113, 1713.
15. Jackman, L.M.; Sternhell, S. in: Applications of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry, International series of monographs in organic chemistry 1969, 5, Pergamon Press, Oxford, ISBN 0-08-012542-5.
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18. Mc Murry, J. J. Org. React. 1977, 24, 187. Zaugg, H.E. J. Org. React. 1954, 8, 305. Cavicchioli, S.; Savoia, D.; Trombini, C.; Umani-Ronchi, A. J. Org. Chem. 1984, 49, 1246-1251.
19. Mc Murry, J. J. Org. React. 1977, 24, 187. Zaugg, H.E. J. Org. React. 1954, 8, 305. Cavicchioli, S.; Savoia, D.; Trombini, C.; Umani-Ronchi, A. J. Org. Chem. 1984, 49, 1246-1251.
20. Articles of related interest: Boger, D.L.; Corbett, W.L.; Curran, T.T.; Kasper, A.M. J. Am. Chem. Soc. 1991, 773, 1713-1729; Gilchrist, T. L. Tetrahedron Lett. 1993, 34, 4097-4100.
21. Articles of related interest: Boger, D.L.; Corbett, W.L.; Curran, T.T.; Kasper, A.M. J. Am. Chem. Soc. 1991, 773, 1713-1729; Gilchrist, T. L. Tetrahedron Lett. 1993, 34, 4097-4100.
22. Bailey, P.D. ; Bryans, J. S. Tetrahedron Lett. 1988, 29, 2231-2234.