Resin-bound 4H-1,3-oxazine-masked β-diketones for functionalizing cleavage strategy

Journal of Combinatorial Chemistry

Volumn 6, Issue 5, 2004, Pages 846-850

  Vanier, Cécile ^a   Wagner, Alain ^a   Mioskowski, Charles ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; ALKYNE DERIVATIVE; AMIDE; DIKETONE; HYDRAZINE DERIVATIVE; OXAZINE DERIVATIVE; PYRAZOLE DERIVATIVE; RESIN;

ARTICLE; CHEMICAL BINDING; POLYMERIZATION; SOLID; SYNTHESIS;

EID: 4944240186     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc030109d     Document Type: Article

References (30)

1. (a) Krchnák, V.; Holladay, M. W. Chem. Rev. 2002, 102, 61-91.
2. (b) Sammelson, R. B.; Kurth, M. J. Chem. Rev. 2001, 101, 137-202.
3. (a) Rana, S.; White, P.; Bradley, M. J. Comb. Chem. 2001, 3, 9-15.
4. (b) Rademan, J.; Smerda, J.; Jung, G.; Grosche, P.; Schmid, D. Angew. Chem., Int. Ed. 2001, 40, 381-385.
5. (c) Gennari, C.; Ceccarelli, S.; Piarulli, U.; Aboutayab, K.; Donghi, M.; Paterson, I. Tetrahedron 1998, 54, 14999-15016.
6. (a) Bräse, S.; Schroen, M. Angew. Chem. 1999, 111, 1139-1142; Angew. Chem., Int. Ed. 1999, 38, 1070-1071.
7. (a) Bräse, S.; Schroen, M. Angew. Chem. 1999, 111, 1139-1142; Angew. Chem., Int. Ed. 1999, 38, 1070-1071.
8. (b) Bräse, S.; Enders, D.; Köbberling, J.; Avemaria, F. Angew. Chem. 1998, 110, 3614-3616; Angew. Chem., Int. Ed. 1998, 37, 3513-3515.
9. (b) Bräse, S.; Enders, D.; Köbberling, J.; Avemaria, F. Angew. Chem. 1998, 110, 3614-3616; Angew. Chem., Int. Ed. 1998, 37, 3513-3515.
10. (c) Nicolaou, K. C.; Pastor, J.; Wissinger, N.; Murphy, F. J. Am. Chem. Soc. 1998, 120, 5132-5133.
11. (d) Vanier, C.; Lorgé, F.; Wagner, A.; Mioskowski, C. Angew. Chem., Int. Ed. 2000, 39, 1679-1683; Angew. Chem. 2000, 112, 1745-1748.
12. (d) Vanier, C.; Lorgé, F.; Wagner, A.; Mioskowski, C. Angew. Chem., Int. Ed. 2000, 39, 1679-1683; Angew. Chem. 2000, 112, 1745-1748.
13. (e) Spivey, A. C.; Diaper, C. M.; Adams, H. J. Org. Chem. 2000, 65, 5253-5263.
14. (a) Shen, D.-M.; Shu, M.; Chapman, K. T. Org. Lett. 2000, 2, 2789-2792.
15. (b) Marzinzik, A. L.; Felder, E. R. Tetrahedron Lett. 1996, 37, 1003-1006.
16. (c) Stauffer, S. R.; Katznellenbogen, J. A. J. Comb. Chem. 2000, 2, 318-329.
17. (d) Nicolaou, K. C.; Cao, G.-Q.; Pfefferkorn, J. A. Angew. Chem., Int. Ed. 2000, 39, 739-743.
18. (e) Srivastava, S. K.; Haq, W.; Chauban, P. M. S. Comb. Chem. High Throughput Screening 1999, 2, 33-37.
19. (f) Trautwein, A. W.; Süssmuth, R. D.; Jung, G. Bioorg Med. Chem. Lett. 1998, 8, 2381-2384.
20. (a) Wilson, R. D.; Watson, S. P.; Richards, S. A. Tetrahedron Lett. 1998, 39, 2827-2830.
21. (b) Shankar, B. B.; Yang, D. Y.; Giron, S.; Ganguly, A. K. Tetrahedron Lett. 1998, 39, 2447-2448.
22. (c) Haap, W. J.; Kaiser, D.; Walk, T. B.; Jung, G. Tetrahedron 1998, 54, 3705-3724.
23. (a) Schmidt, R. R. Synthesis 1972, 333-350.
24. (b) Yamamoto, Y.; Azuma, Y.; Ohnishi, S. Heterocycles 1981, 15, 851-856.
25. (a) Schmidt, R. R. Synthesis 1972, 333-350.
26. (b) Katritzky, A. R.; Pernak, J.; Fan, W.-Q. Synthesis 1994, 445-456.
27. (c) Giordano, C.; Abis, L. Gazz. Chim. Ital. 1974, 104, 1181-1193.
28. Vanier, C.; Wagner, A.; Mioskowski, C. Chem.-Eur. J. 2001, 7, 2313-2323.
29. Lorgé, F.; Wagner, A.; Mioskowski, C. J. Comb. Chem. 1999, 1, 25-27.
30. 2 bisbenzylic) ; 1681 (C=N) ; 1605 (Ar-C) ; 1510 ; 1493 ; 1452 ; 1373 (C-N) ; 1250; 1173 (symetrically para-disubstitued aromatic) ; 1029 (out of plane vibrations of C-C or C-H of benzenic rings) ; 842 ; 760 ; 699. Elemental analysis : Élement % calculated % found N 1,00 0,78 O 2,26 1,81 Br 2,78 2,19 Cl 0 0,05