F. Jovic et al. / Tetrahedron Letters46 (2005) 6809–6814
6813
O
O
NPht
P
N
N
(7)
Ph
Et3N, MgSO4
THF
N
67%
O
P
N
NPht
N
Ph
NH2
(18)
(8)
Scheme 7. Imine formation.
12. Pollack, S. J.;Jacobs, J. W.;Schultz, P. G. Science 1986,
234, 1570–1573.
13. Schultz, P. G.;Yin, J.;Lerner, R. A. Angew. Chem., Int.
Ed. 2002, 41, 4427–4437.
14. Hasserodt, J. Synlett 1999, 12, 2007–2022.
15. Reymond, J.-L. Top. Curr. Chem. 1999, 200, 59–93.
16. Vayron, P.;Renard, P. Y.;Valleix, A.;Mioskowski, C.
Chem. Eur. J. 2000, 6, 1050–1063.
highly proteic media, and thus with the immunization
process.
Current efforts are stressed upon the formation of a new
hapten with the C–N double bond stabilized within an
oxazole or thiazole ring. Synthesis and results of the
immunization process will be reported in due time.
´
17. Dias, S.;Jovic, F.;Renard, P. Y.;Taran, F.;Cre
minon,
C.;Mioskowski, C.;Grassi, J. J. Immun. Methods 2002,
269, 81–98.
Acknowledgements
18. Ersoy, O.;Fleck, R.;Blanco, M.-J.;Masamune, S. Bioorg.
Med. Chem. 1999, 7, 279–286.
This work was financially supported by French ministry
19. Ersoy, O.;Fleck, R.;Sinskey, A.;Masamune, S.
J. Am.
´ ´
´ ´
of defence procurement agency (ÔDelegation Generale
pour lÕArmementÕ), through two Ph.D. fellowships
to F.J. and L.L. and the contract DGA/DSP/STTC/
DT-SH # 00-34-031.
Chem. Soc. 1998, 120, 817–818.
20. Mahy, J. P.;Desfosses, B.;de Lauzon, S.;Quilez, R.;
Desfosses, B.;Lion, L.;Mansuy, D.
Appl. Biochem.
Biotechnol. 1998, 75, 103–127.
21. Pollack, S. J.;Nakayama, G. R.;Schultz, P. G. Science
1988, 242, 1038–1040.
22. Pollack, S. J.;Schultz, P. G. J. Am. Chem. Soc. 1989, 111,
1929–1931.
References and notes
1. Taylor, P. In Goodman and GilmanÕsthe Pharmacological
Basis of Therapeutics, 10th ed.;Hardman, J. G., Limbird,
L. E., Goodman, A. G., Eds.;McGraw-Hill: New York,
2001;pp 175–192.
2. Langford, R. E. Introduction to Weaponsof Mass
Destruction, Radiological, Chemical and Biological;John
Wiley and Sons: Chichester, 2004.
3. Convention on the Prohibition of the Development, Produc-
tion, Stockpiling and Use of Chemical Weapons and on their
Destruction; The Technical Secretariat of the Organization
for the Prohibition of Chemical Weapons;Den Hague,
Netherlands, 1993.
23. Um, I. H.;Buncel, E. N. J. Org. Chem. 2000, 65, 577–582.
24. Um, I. K.;Hong, J.-Y.;Buncel, E. Chem. Commun. 2001,
27–28.
25. Hay, R. W.;Govan, N. Chem. Commun. 1990, 714–715.
26. Oh, S. J.;Yoon, C. W.;Park, J. W. J. Chem. Soc., Perkin
Trans. 2 1996, 329–331.
27. Hay, R. W.;Govan, N. Polyhedron 1998, 17, 2079–2085.
28. Kazankov, G. M.;Seergeva, V. S.;Efremenko, E. N.;
Alexandrova, L.;Varfolomeev, S. D.;Ryabov, A. D.
Angew. Chem., Int. Ed. 2000, 39, 3117–3119.
29. Epstein, J.;Callahan, J. J.;Bauer, V. E. Phosphorus 1974,
4, 157–163.
4. Yang, Y. C.;Baker, J. A.;Ward, J. R. Chem. Rev. 1992,
92, 1729–1743.
30. Boulet, C. A.;Hansen, A. S. Phosphorus, Sulfur Silicon
1991, 57, 147–161.
5. Yang, Y. C. Acc. Chem. Res. 1999, 32, 109–115.
6. Crabb, D.;DeFrank, J.;Penet, C. Chem. Ind. 2004, 14,
15.
7. Yang, Y. C.;Berg, F. J.;Szafraniec, L. L.;Beaudry, W. T.;
Bunton, C. A.;Kumar, A. J. Chem. Soc., Perkin Trans. 2
1997, 607–613.
8. Yang, Y. C.;Szafraniec, L. L.;Beaudry, W. T.;Rohr-
baugh, D. K.;Procell, L. R.;Samuel, J. B. J. Org. Chem.
1996, 61, 8407–8413.
9. Renard, P. Y.;Schwebel, H.;Vayron, P.;Josien, L.;
Valleix, A.;Mioskowski, C. Chem. Eur. J. 2002, 8, 2910–
2916.
31. Lundy, P. M.;Hansen, A. S.;Hand, B. T.;Boulet, C. A.
Toxicology 1992, 72, 99–105.
32. Dawson, R. M. J. Appl. Toxicol. 1994, 14, 317–331.
33. Leikin, J. B.;Thomas, R. G.;Walter, F. G.;Klein, R.;
Meislin, H. W. Crit. Care Med. 2002, 10, 2346–2354.
34. Cassagne, T.;Cristau, H. J.;Delmas, G.;Desgranges, M.;
Lion, C.;Magnaud, G.;Torreilles, E.;Virieux, D.
Heteroatom Chem. 2001, 12, 485–490.
35. Wagner, G. W.;Yang, Y. C. Ind. Eng. Chem. Res. 2002,
41, 1925–1928.
36. Morales-Rojas, H.;Moss, R. A. Chem. Rev. 2002, 102,
2497–2521.
´
10. Vayron, P.;Renard, P. Y.;Taran, F.;Cre
minon, C.;
37. Terrier, F.;MacCormack, P.;Kizilian, E.;Halle, J.-C.;
Demersemen, P.;Guir, F.;Lion, C. J. Chem. Soc., Perkin
Trans. 2 1991, 153–158, and references cited therein.
38. Koplovitz, I.;Stewart, J. R. Toxicol. Lett. 1994, 70, 269–
279.
Frobert, Y.;Grassi, J.;Mioskowski, C. Proc. Natl. Acad.
Sci. U.S.A. 2000, 97, 7058–7063.
11. Tramontano, A.;Janda, K. D.;Lerner, R. A.
Science
1986, 234, 1566–1570.