Synthesis of benzisoxazolines by the coupling of arynes with nitrones

Journal of Organic Chemistry

Volumn 77, Issue 5, 2012, Pages 2279-2284

  Lu, Chun ^a   Dubrovskiy, Anton V ^a   Larock, Richard C ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NITRONES; REACTION CONDITIONS;

CHEMISTRY; ORGANIC COMPOUNDS;

FUNCTIONAL GROUPS;

ARYNE; BENZISOXAZOLINE; CHEMICAL COMPOUND; FUNCTIONAL GROUP; NITRONE; OXAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

1,3 DIPOLAR CYCLOADDITION; ARTICLE; CYCLOADDITION; SYNTHESIS;

BENZENE DERIVATIVES; CYCLIZATION; ISOXAZOLES; MOLECULAR STRUCTURE; NITROGEN OXIDES; STEREOISOMERISM;

EID: 84857805439     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo2025064     Document Type: Article

References (36)

1. Raut, A. W.; Doshi, A. G.; Raghuwanshi, R. B. Orient. J. Chem. 1998, 14, 363 and references therein
2. Dai, M.; Wang, Z.; Danishefsky, S. J. Tetrahedron Lett. 2008, 49, 6613
3. Jaeger, V.; Buss, V.; Schwab, W. Tetrahedron Lett. 1978, 34, 3133
4. Sangeeta, S.; Rathi, R.; Doshi, A. G. Orient. J. Chem. 2006, 22, 169
5. Barluenga, J.; Aznar, F.; Palomero, M. A. Chem.-Eur. J. 2001, 7, 5318
6. Kitamura, T.; Todaka, M.; Shin-machi, I.; Fujiwara, Y. Heterocycl. Commun. 1998, 4, 205
7. Lokhande, P. D.; Ghiya, B. J. J. Indian Chem. Soc. 1991, 68, 412
8. Matsumoto, T.; Sohma, T.; Hatazaki, S.; Suzaki, K. Synlett 1993, 843
9. Himeshina, Y.; Sonoda, T.; Kobayashi, H. Chem. Lett. 1983, 1211
10. For the most recent comprehensive review on arynes, see: Chen, Y.; Larock, R. C. In Modern Arylation Methods; Ackerman, J., Ed.; Wiley/VCH: New York, 2009; pp 401-473.
11. Liu, Z.; Larock, R. C. J. Org. Chem. 2006, 71, 3198
12. Zhao, J.; Larock, R. C. J. Org. Chem. 2007, 72, 583
13. Rogness, D.; Larock, R. C. Tetrahedron Lett. 2009, 50, 4003
14. Rogness, D.; Larock, R. C. J. Org. Chem. 2010, 75, 2289
15. Dubrovskiy, A. V.; Larock, R. C. Org. Lett. 2010, 12, 3117
16. Shi, F.; Larock, R. C. Tetrahedron Lett. 2009, 50, 4067
17. Liu, Z.; Shi, F.; Martinez, P. D. G.; Raminelli, C.; Larock, R. C. J. Org. Chem. 2008, 73, 219
18. Shi, F.; Waldo, J.; Chen, Y.; Larock, R. C. Org. Lett. 2008, 10, 2409
19. Dubrovskiy, A. V.; Larock, R. C. Org. Lett. 2010, 12, 1180
20. Wu, Q.; Li, B.; Lin, W.; Shi, C.; Chen, Y.; Chen, Y. Hecheng Huaxue 2007, 15, 292
21. Dai, M.; Wang, Z.; Danishefsky, S. J. Tetrahedron Lett. 2008, 49, 6613
22. Wu, K.; Chen, Y.; Lin, Y.; Cao, W.; Zhang, M.; Chen, J.; Lee, A. W. M. Tetrahedron 2010, 66, 578
23. Matsumoto, T.; Sohma, T.; Hatazaki, S.; Suzuki, K. Synlett 1993, 11, 843
24. Pellissier, H.; Santelli, M. Tetrahedron 2003, 59, 701
25. Dai, M.; Wang, Z.; Danishefsky, S. J. Tetrahedron Lett. 2008, 49, 6613
26. Peña, D.; Pérez, D.; Guitián, E.; Castedo, L. J. Am. Chem. Soc. 1999, 121, 5827
27. Peña, D.; Pérez, D.; Guitián, E.; Castedo, L. J. Org. Chem. 2000, 65, 6944
28. Yoshida, H.; Sugiura, S.; Kunai, A. Org. Lett. 2002, 4, 2767
29. Liu, Z.; Zhang, X.; Larock, R. C. J. Am. Chem. Soc. 2005, 127, 15716
30. Peña, D.; Escudero, S.; Pérez, D.; Guitián, E.; Castedo, L. Angew. Chem., Int. Ed. 1998, 37, 2659
31. Yoshida, H.; Ikadai, J.; Shudo, M.; Ohshita, J.; Kunai, A. J. Am. Chem. Soc. 2003, 125, 6638
32. Cardona, F.; Bonanni, M.; Soldaini, G.; Goti, A. ChemSusChem. 2008, 1, 327
33. Soldaini, G.; Cardona, F.; Goti, A. Org. Lett. 2007, 9, 473
34. M.-C. Lo, M.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 4572
35. Murray, R. W.; Iyanar, K. J. Org. Chem. 1996, 61, 8099
36. Goti, A.; Nannelli, L. Tetrahedron Lett. 1996, 37, 6025