Synthesis of C5-substituted imidazolines

Tetrahedron Letters

Volumn 44, Issue 51, 2003, Pages 9111-9114

  Defacqz, Nathalie ^a   Tran Trieu, Van ^a   Cordi, Alex ^b   Marchand Brynaert, Jacqueline ^a  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

^b INSTITUT DE RECHERCHES SERVIER   (France)

Author keywords

Imidazoline; Mitsunobu reaction

Indexed keywords

2,3 DIAMINOPROPIONIC ACID; 5 (HYDROXYMETHYL) 3 (TERT BUTYLCARBONYL)IMIDAZOLINE; ACETAMIDE DERIVATIVE; IMIDAZOLINE DERIVATIVE; N BENZYLTRIFLUOROACETAMIDE; PHENOL DERIVATIVE; PHTHALIMIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; MITSUNOBU REACTION; SUBSTITUTION REACTION;

EID: 0344413541     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.10.044     Document Type: Article

References (37)

1. Bousquet P., Feldman J. Drugs. 58:1999;799-812.
2. Gentili F., Bousquet P., Brasili L., Dontenwill M., Feldman J., Ghelfi F., Giannella M., Piergentili A., Quaglia W., Pigini M. J. Med. Chem. 46:2003;2169-2176.
3. Hodson S.J., Bishop M.J., Speake J.D., Navas F. III, Garrison D.T., Bigham E.C., Saussy D.L. Jr., Liacos J.A., Irving P.E., Gobel M.J., Sherman B.W. J. Med. Chem. 45:2002;2229-2239.
4. Anastassiadou M., Danoun S., Crane L., Baziard-Mouysset G., Payard M., Caignard D.-H., Rettori M.-C., Renard P. Bioorg. Med. Chem. 9:2001;585-592.
5. Dardonville C., Rozas I., Callado L.F., Meana J. J. Bioorg. Med. Chem. 10:2002;1525-1533.
6. Bousquet P. J. Cardiovasc. Pharm. 35:2002;S21-S25.
7. Touzeau F., Arrault A., Guillaumet G., Scalbert E., Pfeiffer B., Rettori M.-C., Renard P., Mérour J.-Y. J. Med. Chem. 46:2003;1962-1979.
8. Cordi A.A., Berque-Bestel I., Persigand T., Lacoste J.-M., Newman-Tancredi A., Audinot V., Milan M.J. J. Med. Chem. 44:2001;787-805.
9. Garcia-Sevilla J.A., Escriba P.V., Walzer C., Bouras C., Guimon J. Neurosci. Lett. 247:1998;95-98.
10. Gargalidis-Moudanos C., Pizzinat N., Javoy-Agid F., Remaury A., Parini A. Neurochem. Int. 30:1997;31-36.
11. Cordi A.A., Lacoste J.-M., Descombes J.-J., Courcahy C., Vanhoutte P.M., Laubie M., Verbeuren T.J. J. Med. Chem. 38:1995;4056-4069.
12. Chan S.L.F., Brown C.A., Morgan N.G. Eur. J. Pharmoacol. 230:1993;375-378.
13. Martin P.K., Matthews H., Rapoport H., Thyagarajan G. J. Org. Chem. 33:1968;3759-3761.
14. Taylor E.C., Ehrhart W.A. J. Org. Chem. 28:1962;1108-1112.
15. Ronan B., Hegedus L.S. Tetrahedron. 49:1993;5549-5563.
16. 3); δ 27.9, 45.6, 52.3, 68.7, 82.4, 149.5, 150.2, 170.8. MS m/z (EI) 228, 169, 155, 127, 69.
17. 3: C, 53. 08; H, 8.05; N, 13.99; found: C, 53.22; H, 7.99; N, 13.67.
18. Knochel P., Singer R.D. Chem. Rev. 93:1993;2117-2188.
19. Knochel P., Perea J.J.A., Jones P. Tetrahedron. 54:1998;8275-8319.
20. Hanessian S., Ponpipom M.M., Lavallée P. Carbohydr. Res. 24:1972;45-56.
21. Jäger V., Häfele B. Synthesis. 1987;801-806.
22. Mitsunobu O. Synthesis. 1981;1-28.
23. Simon C., Sandor H., Dor M. J. Heterocycl. Chem. 34:1997;349-357.
24. Hughes D.L. Org. React. 42:1992;335-656.
25. 2/i-PrOH, 98/2).
26. -1) 3054, 1719, 1617, 1594, 1385, 1344.
27. Landini D., Penso M. Synth. Commun. 18:1988;791-800.
28. Boland N.A., Casey M., Hynes S.J., Matthews J.W., Smyth M.P. J. Org. Chem. 67:2002;3919-3922.
29. Cordi A.A., Lacoste J.-M., Le Borgne F., Herve Y., Vaysse-Ludot L., Descombes J.-J., Courchay C., Laubie M., Verbeuren T.J. J. Med. Chem. 40:1997;2931-2935.
30. Hsiao Y., Hegedus L.S. J. Org. Chem. 62:1997;3586-3591.
31. Moehrle H., Kamper C. Pharmazie. 39:1984;673-681.
32. Martin P.K., Matthews H.R., Rapoport H., Thyagarajan G. J. Org. Chem. 33:1968;3758-3761.
33. Hayashi T., Kishi E., Soloshonok V.A., Uozumi Y. Tetrahedron Lett. 37:1996;4969-4972.
34. Zhou X.-T., Lin Y.-R., Dai L.-X., Sun J., Xia L.-J., Tang M.-H. J. Org. Chem. 64:1999;1331-1334.
35. Jung S.-H., Kohn H. Tetrahedron Lett. 25:1984;399-402.
36. Meyer R., Schöllkopf U., Böhme P. Liebigs Ann. Chem. 1977;1183-1193.
37. 5: C, 57.53; H, 5.52; N, 9.58; found: C, 57.33; H, 5. 52; N, 9.57.