Aromatic N-N exchange reactions of N,N-dimethylamino gem-difluorinated heterocycles. A convenient synthesis of new 5-imidazol-1-yl α,α- difluoroketones

Tetrahedron Letters

Volumn 37, Issue 29, 1996, Pages 5119-5122

  Médebielle, Maurice ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BENZIMIDAZOLE; FLUORINATED HYDROCARBON; HETEROCYCLIC KETONE; IMIDAZOLE; IMIDAZOLE DERIVATIVE;

ARTICLE; CYCLIZATION; ELECTROLYSIS; FLUORINATION; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0030586141     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01064-7     Document Type: Article

References (15)

1. 1. (a) Burger, K.; Wucherpfennig, U.; Brunner, E. Adv. Heterocycl. Chem. 1994, 60, 1.
2. (b) "Biomedicinal Aspects of Fluorine Chemistry", Filler, R.; Kobayashi, Y.; Eds.; Kodensha: Tokyo, 1982.
3. 2. Welch, J. T, Eswarakrishnan, S. "Fluorine in Bioorganic Chemistry", John Wiley & Sons, Inc., New York, 1991.
4. 3. (a). Halliman, E. A.; Fried, J. Tetrahedron Lett. 1984, 25, 2301-2302.
5. (b). Kitagawa, O.; Taguchi, T.; Kobayashi, Y. Tetrahedron Lett. 1988, 29, 1803-1806.
6. (c). Hertel, L. W.; Kroin, J. S.; Misner, J. W.; Tustin, J. M. J. Org. Chem. 1988, 53, 2406-2409.
7. (d). Kitagawa, O.; Taguchi, T.; Kobayashi, Y. Chem. Lett. 1990, 1307-1310.
8. 4. Middleton, W. J. J. Org. Chem. 1975, 40, 574-578.
9. 5. Some new gem-difluorocyclic compounds have been synthesized recently in view of their potential biological activity. (a). Barth, F.; O-Yang, C. Tetrahedron. Lett. 1991, 42, 5873-5876.
10. (b). Taguchi, T.; Kodama, Y.; Kanazawa, M. Carbohydr. Res. 1993, 249, 243-252.
11. (c). Buttle, L. A.; Motherwell, W. B. Tetrahedron. Lett. 1994, 35, 3995-3998.
12. 6. Médebielle, M. Tetrahedron. Lett. 1995, 36, 2071-2074.
13. 7. Some interesting syntheses of fluorine heterocycles were achieved by various aromatic nucleophilic N-N, N-S and N-O exchange reactions followed by cyclizations using N,N-dimethyl-2,4-bis(trifluoroacetyi)-1-napthylamine as substrate: Okada, E.; Masuda, R.; Hojo, M.; Imazaki, N. Heterocycles. 1995, 40, 905-911 and references cited therein.
14. +), Analysis: Calcd. C 67.06, H 4.11, N 8.23. Found. C 67.28, H 4.24, N 8.32.
15. 9. Kumar, V.; McCloskey, P.; Bell, M. R, Tetrahedron. Lett. 1994, 35, 833-834.