A practical synthesis of ureas from phenyl carbamates

Synthesis

Volumn , Issue 10, 1997, Pages 1189-1194

  Thavonekham, Bounkham ^a  

^a BOEHRINGER INGELHEIM CANADA LTD   (Canada)

Author keywords

DMSO as solvent; Mild conditions; Phenyl carbamates; Unsymmetrical ureas

Indexed keywords

CARBAMIC ACID DERIVATIVE; UREA DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STOICHIOMETRY;

EID: 0030780333     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1335     Document Type: Article

References (48)

1. Matsuda, K. Med. Res. Rev. 1994, 14, 271.
2. Sandler, S.R.; Karo, W. In Organic Functional Group Preparations; Academic: New York, 1971; Vol. II, pp 152-191.
3. Shriner, R.L.; Horne, W.H.; Cox, R.F. Org. Synth. 1943, 2, 453.
4. Nowick, J.S.; Powell, N.A.; Nguyen, T.M.; Noronha, G. J. Org. Chem. 1992, 57, 7364.
5. Kurita, K.; Matsumura, T.; Iwakura, Y. J. Org. Chem. 1976, 41, 2070.
6. Kurita, K.; Iwakura, Y. In Org. Synth. Coll. VI; Wiley: New, York, 1988; p 715.
7. Eckert, H.; Forster, B. Angew. Chem. 1987, 99, 992;
8. Angew. Chem., Int. Ed. Engl. 1987, 26, 894.
9. Randad, R.S.; Majer, P. J. Org. Chem. 1994, 59, 1937.
10. Cotarca, L.; Delogu, P.; Nardelli, A.; Šunjic, V. Synthesis 1996, 553.
11. Gante, J. Chem. Ber. 1965, 98, 3334.
12. Izdebski, J.; Pawlak, D. Synthesis 1989, 423.
13. Lipkowski, A.W.; Tam, S.W.; Portoghese, P.S. J. Med. Chem. 1986, 29, 1222.
14. Adamiak, R.W.; Stawinski, J. Tetrahedron Lett. 1977, 18, 1935.
15. Staab, H.A. Liebigs Ann. Chem. 1957, 609, 75.
16. Wang, X.C.; Kempf, D.J. 202nd ACS National Meeting New York, 25-30 August, 1991 (Abstract 106).
17. Ozaki, S. Chem. Rev. 1972, 72, 457.
18. Freer, R.; McKillop, A. Synth. Commun. 1996, 26, 331.
19. Leung, M.-K.; Lai, J.-J.; Lau, K.-H.; Yu, H.-H.; Hsiao, H.-J. J. Org. Chem. 1996, 61, 4175.
20. Basha, A. Tetrahedron Lett. 1988, 29, 2525.
21. Knölker, H.-J.; Braxmeier, T.; Schlechtingen, G. Synlett 1996, 502.
22. Knölker, H.-J.; Braxmeier, T.; Schlectingen, G. Angew. Chem. 1995, 107, 2746;
23. Angew. Chem., Int. Ed. Engl. 1995, 34, 2497.
24. Lamothe, M.; Perez, M.; Colovray-Gotteland, V.; Halazy, S. Synlett 1996, 507.
25. Henson, T.R.; Timberlake, J.F., U.S. Patent 4294774; Chem. Abstr. 1982, 96, 7220n.
26. Hassan, A.A.; Mourad, A.E. Indian J. Chem. 1992, 31B, 277.
27. Crosby, D.G.; Nieemann, C. J. Am. Chem. Soc. 1954, 76, 4458.
28. Forbes, I.T.; Jones, G.E.; Murphy, O.E.; Holland, V.; Baxter, G.S. J. Med. Chem. 1995, 38, 855.
29. Carceller, E.; Merlos, M.; Giral, M.; Almmansa, C.; Bertolli, J.; Garcia-Rafanel, J.; Forn, J. J. Med. Chem. 1993, 36, 2984.
30. Kimura, T.; Watanabe, N.; Matsui, M.; Hayashi, K.; Tanaka, H.; Ohtsuka, I.; Saeki, T.; Kogushi, M.; Kabayashi, H.; Akasaka, K.; Yamagishi, Y.; Saitou, I.; Yamatsu, I. J. Med. Chem. 1993, 36, 1641.
31. Lampe, J.W.; Hana, R.G.; Piscitelli, T.A.; Chou, Y-L.; Erhart, P.W.; Lumma, W.C., Jr.; Greenberg, S.G.; Ingebretsen, W.R.; Marshall, D.C.; Wiggins, J. J. Med. Chem. 1990, 33, 1688.
32. Glamkowski, J.E.; Chiang, Y. J. Heterocycl. Chem. 1987, 24, 733.
33. For a review on DMSO see: Martin, D.; Weise, A.; Niclas, H.-J. Angew. Chem. 1967, 79, 340;
34. Angew. Chem., Int. Ed. Engl. 1967, 6, 318.
35. Corey, E.J.; Suggs, W. J. Org. Chem. 1973, 38, 3223.
36. Gillard, J.; Abraham, A.; Anderson, P.C.; Beaulieu, P.L.; Bogri, T.; Bousquet, Y.; Grenier, L.; Guse, I.; Lavallée, P. J. Org. Chem. 1996, 61, 2226.
37. Menger, F.M.; Glass, L.E. J. Org. Chem. 1974, 39, 2459.
38. 4 (50 mM) in MeCN, 215 nm, 1 mL/min. - Chiral Pak AS (DAICEL 4.6 × 250 mm); 10% EtOH/hexane, 205 nm, 0.5 mL/min.
39. For example, see: Ellman, A.J. Acc. Chem. Res. 1996, 29, 132.
40. When two primary amines (butylamine and isoamylamine) and two secondary amines (dibutylamine and diisoamylamine) were used, a similar reactivity effect was observed. The combined yield (94 and 90 %) and a ratio of 1:1 mixture were obtained respectively.
41. Dibutylamine and butylamine were used under the same conditions.
42. Shawali, A.S.; Hrhash, A.; Sidky, M.M.; Hassaneen, H.M.; Elkaadi, S.S. J. Org. Chem. 1986, 51, 3498.
43. Gregory, W.A.; Brittelli, D.R.; Wang, C.-L.J.; Wuonola, M.A.; McRipley, R.J.; Eustice, D.C.; Eberly, V.S.; Bartholenew, P.T.; Slee, A.M.; Forbes, M. J. Med. Chem. 1989, 32, 1673.
44. Jones, G.H.; Venuti, M.C.; Alvarez, R.; Bruno, J.J.; Berks, A.H.; Prince, A. J. Med. Chem. 1987, 30, 295.
45. Carleton, P.S.; Farrissey, W.J., Jr. Tetrahedron Lett. 1969, 10, 3485.
46. Hegarty, A.F.; Frost, L.N. J. Chem. Soc., Chem. Commun. 1972, 500.
47. Bender, M.L.; Homer, R.B. J. Org. Chem. 1965, 30, 3975.
48. 24 +5.9° (c = 0.66, MeOH).