A novel two-step preparation of enaminoketones by amination of α,β- unsaturated ketones with methoxyamine

Tetrahedron Letters

Volumn 39, Issue 44, 1998, Pages 8117-8120

  Seko, Shinzo ^a   Tani, Nobuhiro ^a  

^a SUMITOMO CHEMICAL CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ENAMINOKETONE; ENONE; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; SYNTHESIS;

EID: 0032578895     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01801-2     Document Type: Article

References (25)

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7. 3. Kashima, C.; Tobe, S.; Sugiyama, N.; Yamamoto, M. Bull. Chem. Soc. Jpn. 1973, 46, 310-313.; Honma, T.; Tada, Y. Heterocycles 1977, 6, 1985-1991.; Iimori, T.; Nii, Y.; Izawa, T.; Kobayashi, S.; Ohno, M. Tetrahedron Lett. 1979, 2525-2528.; Bartoli, G.; Cimarelli, C.; Palmieri, G.; Bosco, M.; Dalpozzo, R. Synthesis 1990, 895-897.; Braibante, M. E. F.; Braibante, H. S.; Missio, L.; Andricopulo, A. Synthesis 1994, 898-900.
8. 3. Kashima, C.; Tobe, S.; Sugiyama, N.; Yamamoto, M. Bull. Chem. Soc. Jpn. 1973, 46, 310-313.; Honma, T.; Tada, Y. Heterocycles 1977, 6, 1985-1991.; Iimori, T.; Nii, Y.; Izawa, T.; Kobayashi, S.; Ohno, M. Tetrahedron Lett. 1979, 2525-2528.; Bartoli, G.; Cimarelli, C.; Palmieri, G.; Bosco, M.; Dalpozzo, R. Synthesis 1990, 895-897.; Braibante, M. E. F.; Braibante, H. S.; Missio, L.; Andricopulo, A. Synthesis 1994, 898-900.
9. 3. Kashima, C.; Tobe, S.; Sugiyama, N.; Yamamoto, M. Bull. Chem. Soc. Jpn. 1973, 46, 310-313.; Honma, T.; Tada, Y. Heterocycles 1977, 6, 1985-1991.; Iimori, T.; Nii, Y.; Izawa, T.; Kobayashi, S.; Ohno, M. Tetrahedron Lett. 1979, 2525-2528.; Bartoli, G.; Cimarelli, C.; Palmieri, G.; Bosco, M.; Dalpozzo, R. Synthesis 1990, 895-897.; Braibante, M. E. F.; Braibante, H. S.; Missio, L.; Andricopulo, A. Synthesis 1994, 898-900.
10. 3. Kashima, C.; Tobe, S.; Sugiyama, N.; Yamamoto, M. Bull. Chem. Soc. Jpn. 1973, 46, 310-313.; Honma, T.; Tada, Y. Heterocycles 1977, 6, 1985-1991.; Iimori, T.; Nii, Y.; Izawa, T.; Kobayashi, S.; Ohno, M. Tetrahedron Lett. 1979, 2525-2528.; Bartoli, G.; Cimarelli, C.; Palmieri, G.; Bosco, M.; Dalpozzo, R. Synthesis 1990, 895-897.; Braibante, M. E. F.; Braibante, H. S.; Missio, L.; Andricopulo, A. Synthesis 1994, 898-900.
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18. (c) Reichel, L.; Pritze, P.Liebigs Ann. Chem. 1974, 120-123.
19. 8. CAUTION Dried methoxyamine has deflagration potential. Bissot, T. C.; Parry, R. W.; Campbell, D. H. J. Am. Chem. Soc. 1957, 79, 796-800.
20. +), 222, 146, 117, 103, 91, 77, 65, 51, 39.
21. 10. CAMEO is an interactive computer program capable of predicting pKa values for organic compounds, developed by Jorgensen. See: Gushurst, A. J.; Jorgensen, W. L.J. Org. Chem. 1986, 51, 3513-3522.
22. 11. The pKa values of α-and β-positions of the substrates in DMSO predicted by CAMEO are depicted as follows. (formula presented)
23. 12. Probable reaction pathway is illustrated as follows. (formula presented)
24. +).
25. 2. Silica gel thin layer chromatography gave pure enaminoketone 7.