Synthesis of celecoxib via 1,3-dipolar cycloaddition

Tetrahedron Letters

Volumn 47, Issue 45, 2006, Pages 7943-7946

  Oh, Lynette M ^a  

^a GLAXOSMITHKLINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENESULFONIC ACID DERIVATIVE; CELECOXIB; ENAMINE; IMINE;

ARTICLE; CHEMICAL REACTION; CYCLOADDITION; DRUG SYNTHESIS;

EID: 33749253109     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.08.138     Document Type: Article

References (28)

1. Letendre, L.; McGhee, W. D.; Snoddy, C.; Klemm, G.; Gaud, H. T. WO 03/09974 A1.
2. Reddy, M.; Ramana, V.; Bell, S. C. WO 03/024400 A2.
3. Bianchi G., DeMicheli C., and Gandolfi R. 1,3-Dipolar Cycloadditions Involving X = Y Groups. In: Patai S. (Ed). The Chemistry of Double Bonded Functional Groups (1977), Interscience, London 369-532
4. Carruthers W. Cycloaddition Reactions in Organic Synthesis (1990), Pergamon Press, New York
5. Rai K.M.L., and Hassner A. Synth. Commun. 19 (1989) 2799
6. Rai K.M.L., and Linganna N. Synth. Commun. 27 (1997) 3737
7. Chen D.W., and Chen Z.C. Synth. Commun. 25 (1995) 1617
8. Bishop J.E., Flaxman K.A., Orlek B.S., Sammes P.G., and Weller D.J. J. Chem. Soc., Perkin Trans. 1 (1995) 2551
9. Gladstone W.A.F., Aylward J.B., and Norman K.O.C. J. Chem. Soc. (1969) 2587
10. Clovis H.S., Eckell A., Huisgen R., and Sustmann R. Chem. Ber. 100 (1967) 60
11. Huisgen R. Angew. Chem. 72 (1960) 359
12. Butler R.N. Adv. Heterocycl. Chem. 21 (1977) 323
13. Sauer J., and Mayer K.K. Tetrahedron Lett. 9 (1968) 325
14. Marky M., Meier J., Wunderli A., Heimgartner H., Schmid H., and Hansen H.J. Helv. Chim. Acta 61 (1978) 1477
15. Ollis W.D., and Ramsden C.A. Adv. Heterocycl. Chem. 19 (1976) 1
16. Gotthard H., and Reiter F. Tetrahedron Lett. 12 (1971) 2749
17. Pfoetner K.H., and Foricher J. Helv. Chim. Acta 63 (1980) 653
18. Tanaka K., Maeno S., and Mitsuhashi K. J. Heterocyl. Chem. 22 (1985) 565
19. Tanaka K., Maeno S., and Mitsuhashi K. Chem. Lett. 4 (1982) 543
20. Shawali A.S., and Párkányi C. J. Heterocyl. Chem. 17 (1980) 833
21. Sharp J.T. Nitrile Ylides and Nitrile Imines. In: Padwa A., and Pearson W.H. (Eds). 1,3-Dipolar Cycloadditions (2002), Interscience, New York 376-378
22. Zhou, J.; Oh, L. M.; Confalone, P.; Li, H. Y.; Ma, P. U.S. Patent 6,329,527 B1.
23. Zhou, J.; Oh, L. M.; Ma, P.; Li, H. Y. WO 03/049681.
24. Enamines have been used previously with nitrile imines to enhance the reactivity. See:. Nomura Y., Takeuchi Y., Tomoda S., and Ito M. Bull. Chem. Soc. Jpn. 54 (1981) 261
25. Meilahn M., Cox B., and Munk M. J. Org. Chem. 40 (1975) 819
26. For studies on the relative reactivity of olefins as dipolarophiles, including the effects of 1,1- versus 1,2-substitution, see:. Jäger V., and Colinas P.A. Nitrile Oxides. In: Padwa A., and Pearson W.H. (Eds). 1,3-Dipolar Cycloadditions (2002), Interscience, New York 376-378
27. 2, 0 °C; (ii) morpholine 5 equiv, THF, 20 °C. {A figure is presented}
28. Modified procedure of. Carlson R., Nilsson Å., and Strömquist M. Acta Chem. Scand. B37 (1983) 7