Convenient Approach to 3,4-Diarylisoxazoles Based on the Suzuki Cross-Coupling Reaction

Advanced Synthesis and Catalysis

Volumn 344, Issue 10, 2002, Pages 1146-1151

  Dileep Kumar, J S ^a,b   Ho, ManKit M ^a   Leung, Jennifer M ^a   Toyokuni, Tatsushi ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b NEW YORK STATE PSYCHIATRIC INSTITUTE   (United States)

Author keywords

3,4 diarylisoxazoles; COX 2 inhibitors; Cross coupling; Heterocycles; Suzuki reaction

Indexed keywords

EID: 0347268362     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/1615-4169(200212)344:10<1146::AID-ADSC1146>3.0.CO;2-1     Document Type: Article

References (38)

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15. [8]) started from the 1,2-diarylethanone and 3,4-diaryl-3-buten-2-one derivatives, respectively. Most of these starting compounds are not commercially available and thereby need to be synthesized.
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22. Combinatorial approaches to isoxazoles have been reported. However, these methods are not suitable for the selective and rapid synthesis of 3,4-diarylsioxazoles. See: a) A. L. Marzinzik, E. R. Felder, Molecules 1997, 2, 17-30; b) B. B. Shankar, D. Y. Yang, S. Girton, A. K. Ganguly, Tetrahedron Lett. 1998, 39, 2447-2448; c) D.-M. Shen, M. Shu, K. T. Chapman, Org. Lett. 2000, 2, 2789-2792.
23. Combinatorial approaches to isoxazoles have been reported. However, these methods are not suitable for the selective and rapid synthesis of 3,4-diarylsioxazoles. See: a) A. L. Marzinzik, E. R. Felder, Molecules 1997, 2, 17-30; b) B. B. Shankar, D. Y. Yang, S. Girton, A. K. Ganguly, Tetrahedron Lett. 1998, 39, 2447-2448; c) D.-M. Shen, M. Shu, K. T. Chapman, Org. Lett. 2000, 2, 2789-2792.
24. Combinatorial approaches to isoxazoles have been reported. However, these methods are not suitable for the selective and rapid synthesis of 3,4-diarylsioxazoles. See: a) A. L. Marzinzik, E. R. Felder, Molecules 1997, 2, 17-30; b) B. B. Shankar, D. Y. Yang, S. Girton, A. K. Ganguly, Tetrahedron Lett. 1998, 39, 2447-2448; c) D.-M. Shen, M. Shu, K. T. Chapman, Org. Lett. 2000, 2, 2789-2792.
25. The compound 5 has been synthesized by different methods. For example, see: a) M. Yokoyama, K. Tsuji, M. Kushida, J. Chem. Soc. Perkin Trans. 1 1986, 67-72; b) O. Moriya, Y. Urata, T. Endo, J. Chem. Soc. Chem. Commun. 1991, 884-885; c) W. H. Bunnelle, P. R. Singam, B. A. Narayanan, C. W. Bradshaw, J. S. Liou, Synthesis 1997, 439-442.
26. The compound 5 has been synthesized by different methods. For example, see: a) M. Yokoyama, K. Tsuji, M. Kushida, J. Chem. Soc. Perkin Trans. 1 1986, 67-72; b) O. Moriya, Y. Urata, T. Endo, J. Chem. Soc. Chem. Commun. 1991, 884-885; c) W. H. Bunnelle, P. R. Singam, B. A. Narayanan, C. W. Bradshaw, J. S. Liou, Synthesis 1997, 439-442.
27. The compound 5 has been synthesized by different methods. For example, see: a) M. Yokoyama, K. Tsuji, M. Kushida, J. Chem. Soc. Perkin Trans. 1 1986, 67-72; b) O. Moriya, Y. Urata, T. Endo, J. Chem. Soc. Chem. Commun. 1991, 884-885; c) W. H. Bunnelle, P. R. Singam, B. A. Narayanan, C. W. Bradshaw, J. S. Liou, Synthesis 1997, 439-442.
28. The oximes 3 and 4 were prepared from acetophenone and 4′-fluoroacetophenone, respectively, see: B. J. Gregory, R. B. Moodie, K. Schofield, J. Chem. Soc. B 1970, 338-346.
29. [9] pp. 337-340.
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32. The boronic acid 13 was prepared from 18 by 4,4′-dimethoxytritylation, followed by a sequence of metallation and boration, and used without extensive characterization (see Experimental Section).
33. It is reported that arylboronic acids bearing electron-withdrawing groups are prone to deboronation with base, see: S. Saito, S. Oh-tani, N. Miyaura, J. Org. Chem. 1997, 62, 8024-8030, and references cited therein.
34. The aryl bromides 17 and 20 are commercially available. Other aryl bromides are known; for 18, see: D. Cheshire, M. Stocks (Astra Pharmaceuticals Ltd.), WO 0018730, 2000; Chem. Abstr. 2000, 132, 265088; for 19, see: D. F. Hayman, V. Petrow, O. Stephenson, J. Pharm. Pharmacol. 1962, 14, 522-533.
35. The aryl bromides 17 and 20 are commercially available. Other aryl bromides are known; for 18, see: D. Cheshire, M. Stocks (Astra Pharmaceuticals Ltd.), WO 0018730, 2000; Chem. Abstr. 2000, 132, 265088; for 19, see: D. F. Hayman, V. Petrow, O. Stephenson, J. Pharm. Pharmacol. 1962, 14, 522-533.
36. Aryl halides bearing an electron-withdrawing group are generally more reactive in cross-coupling reactions than the corresponding unsubstituted aryl halides. For discussions, see: V. V. Grushin, H. Alper, Chem. Rev. 1994, 94, 1047-1062.
37. [19] and references cited therein.
38. 19F NMR spectra are available upon request.