A new method for synthesis of unsymmetrical ureas using electrochemically prepared trifluoroethyl carbamates

Journal of Organic Chemistry

Volumn 65, Issue 5, 2000, Pages 1549-1551

  Matsumura, Yoshihiro ^a,b   Satoh, Yuki ^a   Onomura, Osamu ^b   Maki, Toshihide ^a,c  

^a KYUSHU UNIVERSITY   (Japan)

^b Faculty of Pharmaceutical Sciences   (Japan)

^c NAGASAKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAMIC ACID DERIVATIVE; UREA DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ELECTROCHEMISTRY; REACTION ANALYSIS; SYNTHESIS;

AMINES; CARBAMATES; ELECTROCHEMISTRY; FLUORIDES; FORMIC ACID ESTERS; MAGNETIC RESONANCE SPECTROSCOPY; UREA;

EID: 0034629295     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991076k     Document Type: Article

References (22)

1. (a) Vishnyakowa, T. P. ; Golubeva, I. A. ; Glebova, E. V. Russ. Chem. Rev. (Engl. Transi. ) 1985, 54, 249.
2. (b) Getman, D. P. ; DeCrescenzo, G. A. ; Heintz, R. M. ; Reed, K. L. ; Tally, J. J. ; Bryant, M. L. ; Clare, M. ; Houseman, K. A. ; Man-, J. J. ; Mueller, R. A. ; Vazquez, M. L. ; Shieh, H. -S. ; Stallings, W. C. ; Stegeman, R. A. J. Med. Chem. 1993, 36, 288.
3. Matsuda, K. Med. Res. Rev. 1994, 14, 271.
4. Peterson, U. In Methoden der Organischen Chemie, HoubenWeyl, E4; G. Thieme Verlag: New York, 1983; p 334.
5. (b) Majer, P. ; Randad, R. S. J. J. Org. Chem. 1994, 59, 1937.
6. Katritzky, A. R. ; Pleynet, D. P. M. ; Yahg, B. J. Org. Chem. 1997, 62, 4155.
7. Sonoda, N. ; Yasuhara, T. ; Kondo, K. ; Tsutsumi, S. J. Am. Chem. Soc. 1971, 93, 691.
8. (e) Yamazaki, N. ; Iguchi, T. ; Higashi, F. Tetrahedron 1975, 31, 3031.
9. (a) Ozaki, S. Chem. Rev. 1972, 72, 457-496.
10. (b) Reichen, W. Helv. Chim. Acta 1977, 60, 498-506.
11. Knölker, H. -J. ; Braxmeier, T. ; Schlechtingen, G. Synlett 1996, 503.
12. Batey, R. A. ; Santhakumar, V. ; Y. -Ishii, C. ; Taylor, S. D. Tetrahedron Lett. 1998, 39, 6267.
13. Basha, A. Tetrahedron Lett. 1988, 29, 2525.
14. (a) Adamiak, R. W. ; Stawinski, J. Tetrahedron Lett. 1977, 22, 1935.
15. (b) Thavonekham, B. Synthesis 1997, 1189.
16. Lamothe, M. ; Perez, M. ; C-Gotteland, V. ; Halazy, S. Synlett 1996, 507.
17. The kinetic study on the leaving ability of trifluoroethoxy group has already been reported; Aquirre, I. De; Collot, J. Bull. Soc. Chim. Belg. 1989, 98, 19.
18. (a) Matsumura, Y. ; Maki, T. ; Satoh, Y. Tetrahedron Lett. 1997, 38, 8879.
19. (b) Matsumura, Y. ; Maki, T. ; Satoh, Y. ; Onomura, O. Electrochim. Acta 2000, in press.
20. Riddick, J. A. ; Hunger, W. B. ; Sakano, T. K In Organic Solvents, 4th ed. ; John Wiley & Sons: New York, 1986; p 700.
21. Carbamate 8a was 2 times reactive than 7a in the reaction with piperidine in THF in the presence of NaH (reflux, 3 h).
22. Nee, R. Chem. Prum. 1979, 29, 589.