Pd(II)-catalyzed synthesis of benzisoxazolones from benzohydroxamic acids via C-H activation

Journal of Organic Chemistry

Volumn 77, Issue 17, 2012, Pages 7700-7705

  Gao, Xi Ai ^a   Yan, Ru Long ^a   Wang, Xian Xue ^a   Yan, Hao ^a   Li, Jian ^a   Guo, Han ^a   Huang, Guo Sheng ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOHYDROXAMIC ACID; C-H ACTIVATION; CATALYZED SYNTHESIS; ONE-POT PROCEDURES;

ACTIVATION ANALYSIS; CATALYSIS;

PALLADIUM COMPOUNDS;

1 (3,5 DIMETHYLBENZOYL) 5,7 DIMETHYLBENZO[C]ISOXAZOL 3(1H) ONE; 1 [(1,1' BIPHENYL) 4 CARBONYL] 6 PHENYLBENZO[C]ISOXAZOL 3(1H) ONE; 1 BENZOYLBENZO[C]ISOXAZOL 3(1H) ONE; 3 (1 NAPHTHOYL)NAPHTHO[2,1 C]ISOXAZOL 1(3H) ONE; 4 CHLORO 1 (2 CHLORO 4 FLUOROBENZOYL) 6 FLUOROBENZO[C]ISOXAZOL 3(1H) ONE; 4 CHLORO 1 (2 CHLOROBENZOYL)BENZO[C]ISOXAZOL 3(1H) ONE; 5 CHLORO 1 (3 CHLOROBENZOYL)BENZO[C]ISOXAZOL 3(1H) ONE; 5 METHYL 1 (3 METHYLBENZOYL)BENZO[C]ISOXAZOL 3(1H) ONE; 6 (BENZYLOXY) 1 [4 (BENZYLOXY)BENZOYL]BENZO[C]ISOXAZOL 3(1H) ONE; 6 BENZOYL 1 (4 BENZOYLBENZOYL)BENZO[C]ISOXAZOL 3(1H) ONE; 6 CHLORO 1 (4 CHLOROBENZOYL)BENZO[C]ISOXAZOL 3(1H) ONE; 6 ETHYL 1 (4 ETHYLBENZOYL)BENZO[C]ISOXAZOL 3(1H) ONE; 6 FLUORO 1 (3 FLUOROBENZOYL)BENZO[C]ISOXAZOL 3(1H) ONE; 6 FLUORO 1 (4 FLUORO 2 METHYLBENZOYL) 4 METHYLBENZO[C]ISOXAZOL 3(1H) ONE; 6 FLUORO 1 (4 FLUOROBENZOYL)BENZO[C]ISOXAZOL 3(1H) ONE; 6 ISOPROPYL 1 (4 ISOPROPYLBENZOYL)BENZO[C]ISOXAZOL 3(1H) ONE; 6 METHYL 1 (4 METHYLBENZOYL)BENZO[C]ISOXAZOL 3(1H) ONE; BENZISOXAZOLONE DERIVATIVE; BENZOHYDROXAMIC ACID; CARBON; HETEROCYCLIC COMPOUND; HYDROGEN; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL BOND; DRUG STRUCTURE; DRUG SYNTHESIS; ONE POT SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; TEMPERATURE;

BENZOXAZOLES; CATALYSIS; HYDROXAMIC ACIDS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PALLADIUM; STEREOISOMERISM;

EID: 84866082530     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo301180k     Document Type: Article

References (40)

1. Li, J.-J., Corey, E. J., Eds. Name Reactions in Heterocyclic Chemistry; Wiley-Interscience: Hoboken, NJ, 2005.
2. Eicher, T.; Hauptmann, S. The Chemistry of Heterocycles; Wiley-VCH: Weinheim, Germany, 2003.
3. Katrizky, A. R.; Pozharskii, A. F. Handbook of Heterocyclic Chemistry; 2 nd ed.; Pergamon: Amsterdam, 2000.
4. Dick, A. R.; Sanford, M. S. Tetrahedron 2006, 62, 2439
5. Godula, K.; Sames, D. Science 2006, 312, 67
6. Mei, T. S.; Wang, X.; Yu, J. Q. J. Am. Chem. Soc. 2009, 131, 10806
7. Tan, Y.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 3676
8. Evans, P. A., Ed. Modern Rhodium-Catalyzed Organic Reactions; Wiley-VCH: Weinheim, Germany, 2005.
9. Davies, H. M. L.; Manning, J. R. Nature 2008, 451, 417
10. Christmann, M. Angew. Chem., Int. Ed. 2008, 47, 2740
11. Guimond, N.; Gorelsky, S. I.; Fagnou, K. J. Am. Chem. Soc. 2011, 133, 6449
12. Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094
13. Xu, L.-M.; Li, B.-J.; Yang, Z.; Shi, Z.-J. Chem. Soc. Rev. 2010, 39, 712
14. Sehnal, P.; Taylor, R. J. K.; Fairlamb, I. J. S. Chem. Rev. 2010, 110, 824
15. Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215
16. Ding, S.; Shi, Z.; Jiao, N. Org. Lett. 2010, 12, 1540
17. Shi, Z.; Zhang, C.; Li, S.; Pan, D.; Ding, S.; Cui, Y.; Jiao, N. Angew. Chem., Int. Ed. 2009, 48, 1
18. Zaitsev, V. G.; Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 13154
19. Beck, E. M.; Grimster, N. P.; Hatley, R.; Gaunt, M. J. J. Am. Chem. Soc. 2006, 128, 2528
20. Lebrasseur, N.; Larrosa, I. J. Am. Chem. Soc. 2008, 130, 2926
21. Wasa, M.; Yu, J.-Q. J. Am. Chem. Soc. 2008, 130, 14058
22. Wang, D.-H.; Wasa, M.; Giri, R.; Yu, J.-Q. J. Am. Chem. Soc. 2008, 130, 7190
23. Conti, P.; Dallanoce, C.; Amici, M. D.; Micheli, C. D.; Klotz, K. N. Bioorg. Med. Chem. 1998, 6, 401
24. Gordaliza, M. G.; Faircloth, T.; Castro, M. A.; del Corral, J. M. M.; Ĺ?opez-V́?azquez, M. L.; San Feliciano, A. J. Med. Chem. 1996, 39, 2865
25. Kwon, T.; Heimann, A. S.; Oriaku, E. T.; Yoon, K. J. Med. Chem. 1995, 38, 1048
26. Kang, Y. Y.; Shin, K. J.; Yo, K. H.; Seo, K. J.; Hong, C. Y.; Lee, C. S.; Park, S. Y.; Kim, D. J.; Park, S. W. Bioorg. Med. Chem. Lett. 2000, 10, 95
27. Abbiati, G.; Beccalli, E. M.; Broggini, G.; Zoni, C. Tetrahedron 2003, 59, 9887
28. Wyrȩbska, A.; Gach, K.; Szemraj, J.; Szewczyk, K.; Hrabec, E.; Koszuk, J.; Janecki, T.; Janecka, A. Chem. Biol. Drug Des. 2012, 79, 112
29. Prediger, P.; Barbosa, L. F.; Génisson, Y.; Correia, C. R. D. J. Org. Chem. 2011, 76, 7737
30. Arfaouia, A.; Beltaïefa, I.; Amria, H. Synth. Commun. 2011, 41, 1536
31. Snyder, L. B.; Meng, Z. X.; Mate, R.; D'Andrea, S. V.; Marinier, A.; Quesnelle, C. A.; Gill, P.; DenBleyker, K. L.; Fung-Tomc, J. C.; Frosco, M. B.; Martel, A.; Barrett, J. F.; Bronson, J. J. Bioorg. Med. Chem. Lett. 2004, 14, 4735
32. Zhou, Q.; Snider, B. B. Org. Lett. 2009, 11, 2936
33. Zhou, Q.; Snider, B. B. J. Org. Chem. 2010, 75, 8224
34. Chu, J.-H.; Chen, Y.-J.; Wu, M.-J. Synthesis 2009, 2155
35. Wang, G.-W.; Yuan, T.-T.; Li, D.-D. Angew. Chem., Int. Ed. 2011, 50, 1380
36. Li, D.-D.; Yuan, T.-T.; Wang, G.-W. Chem. Commun. 2011, 47, 12789
37. Wang, G.-W.; Yuan, T.-T. J. Org. Chem. 2010, 75, 476
38. Cai, G.; Fu, Y.; Li, Y.; Wan, X.; Shi, Z. J. Am. Chem. Soc. 2007, 129, 7666
39. Augustine, J. K.; Akabote, V.; Hegde, S. G.; Alagarsamy, P. J. Org. Chem. 2009, 74, 5640
40. Sasada, T.; Kobayashi, F.; Sakai, N.; Konakahara, T. Org. Lett. 2009, 11, 2161