Microwave-assisted, palladium-catalyzed intramolecular direct arylation for the synthesis of novel fused heterocycles

Synlett

Volumn , Issue 17, 2007, Pages 2728-2732

  Wu, Jinlong ^a   Nie, Liang ^a   Luo, Jialu ^a   Dai, Weimin ^a,b  

^a ZHEJIANG UNIVERSITY   (China)

^b HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

Author keywords

3,4 dihydro 3 oxo 2H 1,4 benzoxazine; Direct arylation; Heterocycles; Microwave; Palladium

Indexed keywords

ACYCLIC ARYL BROMIDE DERIVATIVE; ALKANE DERIVATIVE; ETHYL 2 BROMOALKANOATE DERIVATIVE; N(2 BROMOBENZYL) 2 AMINOPHENOL DERIVATIVE; PALLADIUM ACETATE; PHENOL DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; POTASSIUM CARBONATE; TOLUENE; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; ARYLATION; CATALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; DEBROMINATION; METHODOLOGY; MICROWAVE RADIATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 35648992542     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-991053     Document Type: Article

References (44)

1. (a) Hoshino, O. In The Alkaloids, Vol. 51; Cordell, G. A., Ed.; Academic Press: San Diego, 1998, 323.
2. (b) Lewis, J. R. Nat. Prod. Rep. 2000, 17, 57.
3. (c) Lewis, J. R. Nat. Prod. Rep. 1998, 15, 107.
4. (a) Ríos, J. L.; Máñez, S.; Giner, R. M.; Recio, M. C. In The Alkaloids, Vol. 53; Cordell, G. A., Ed.; Academic Press: New York, 2000, 57.
5. (b) Guinaudeau, H.; Leboeaf, M.; Cavé, A. J. Nat. Prod. 1994, 57, 1033; and references cited therein.
6. For selected reviews, see: (a) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174.
7. (b) Campeau, L.-C.; Fagnou, K. Chem. Commun. 2006, 1253.
8. (c) Echavarren, A. M.; Gómez-Lor, B.; González, J. J.; de Frutos, Ó. Synlett 2003, 585.
9. (a) Harayama, T.; Hori, A.; Abe, H.; Takeuchi, Y. Tetrahedron 2004, 60, 1611.
10. (b) Torres, J. C.; Pinto, A. C.; Garden, S. J. Tetrahedron 2004, 60, 9889.
11. Echavarren, A. M.; Gómez-Lor, B. Org. Lett. 2004, 6, 2993.
12. (a) Cuny, G. D. Tetrahedron Lett. 2003, 44, 8149.
13. (b) Cuny, G. D. Tetrahedron Lett. 2004, 45, 5167.
14. (a) Lafrance, M.; Blaquière, N.; Fagnou, K. Chem. Commun. 2004, 2874.
15. (b) For synthesis of 9-arylphenanthrenes, see: García-Cuadrado, D.; de Mendoza, P.; Braga, A. A. C.; Maseras, F.; Echavarren, A. M. J. Am. Chem. Soc. 2007, 129, 6880.
16. (a) Cuny, G.; Bois-Choussy, M., Zhu, J. Angew. Chem. Int. Ed. 2003, 42, 4774.
17. (b) Cuny, G.; Bois-Choussy, M.; Zhu, J. J. Am. Chem. Soc. 2004, 126, 14475.
18. For examples of microwave-assisted C-H activation using rhodium catalyst, see: (a) Tan, K. L.; Vasudevan, A.; Bergman, R. G.; Ellman, J. A.; Souers, A. J. Org. Lett. 2003, 5, 2131.
19. (b) Lewis, J. C.; Wu, J. Y.; Bergman, R. G.; Ellman, J. A. Angew. Chem. Int. Ed. 2006, 45, 1589.
20. (c) Using palladium catalyst, see: Sridharan, V.; Martín, M. A.; Menendez, J. C. Synlett 2006, 2375.
21. (d) Using nickel catalyst, see: Cioffi, E. A.; Bell, R. H.; Le, B. Tetrahedron: Asymmetry 2005, 16, 471.
22. Also, see: (e) Larhed, M.; Moberg, C.; Hallberg, A. Acc. Chem. Res. 2002, 35, 717.
23. (f) Roberts, B. A.; Strauss, C. R. Acc. Chem. Res. 2005, 38, 653.
24. For selected reviews on controlled microwave heating, see: (a) Nüchter, M.; Ondruschka, B.; Bonrath, W.; Gum, A. Green Chem. 2004, 43, 128.
25. (b) Kappe, C. O. Angew. Chem. Int. Ed. 2004, 43, 6250.
26. For recent monographs, see: (c) Kappe, C. O.; Stadler, A. Microwaves in Organic and Medicinal Chemistry; Wiley-VCH: Weinheim, 2005.
27. (d) Microwaves in Organic Synthesis, Vol. 1 and 2; Loupy, A., Ed.; Wiley-VCH: Weinheim, 2006.
28. For synthesis of indoles, see: (a) Dai, W.-M.; Guo, D.-S.; Sun, L.-P. Tetrahedron Lett. 2001, 42, 5275.
29. (b) Dai, W.-M.; Sun, L.-P.; Guo, D.-S. Tetrahedron Lett. 2002, 43, 7699.
30. (c) Dai, W.-M.; Guo, D.-S.; Sun, L.-P.; Huang, X.-H. Org. Lett. 2003, 5, 2919.
31. (d) Sun, L.-P.; Huang, X.-H.; Dai, W.-M. Tetrahedron 2004, 60, 10983.
32. (e) Sun, L.-P.; Dai, W.-M. Angew. Chem. Int. Ed. 2006, 45, 7255.
33. For synthesis of benzo[b]furanes, see: Dai, W.-M.; Lai, K. W. Tetrahedron Lett. 2002, 43, 9677.
34. For synthesis of 1,4-benzoxazines, see: (a) Dai, W.-M.; Wang, X.; Ma, C. Tetrahedron 2005, 61, 6879.
35. (b) Feng, G.; Wu, J.; Dai, W.-M. Tetrahedron 2006, 62, 4635.
36. (c) Xing, X.; Wu, J.; Feng, G.; Dai, W.-M. Tetrahedron 2006, 62, 6774.
37. (d) Feng, G.; Wu, J.; Dai, W.-M. Tetrahedron Lett. 2007, 48, 401.
38. For synthesis of tetrahydroquinolines, see: Xing, X.; Wu, J.; Dai, W.-M. Tetrahedron 2006, 62, 11200.
39. For synthesis of the conjugates of dibenz[b,f][1,4]oxazepine with 2-oxindole, see: Xing, X.; Wu, J.; Luo, J.; Dai, W.-M. Synlett 2006, 2099.
40. Abdel-Magid, A. F.; Carson, K. G.; Harris, B. D.; Maryanoff, C. A.; Shah, R. D. J. Org. Chem. 1996, 61, 3849.
41. 13C NMR of 7a-f and 16 can be obtained from the authors upon request.
42. (a) Dai, W.-M.; Li, Y.; Zhang, Y.; Lai, K. W.; Wu, J. Tetrahedron Lett. 2004, 45, 1999.
43. (b) Dai, W.-M.; Zhang, Y. Tetrahedron Lett. 2005, 46, 1377.
44. (c) Jin, J.; Chen, Y.; Li, Y.; Wu, J.; Dai, W.-M. Org. Lett. 2007, 9, 2585.