Gold- and silver-catalyzed intramolecular hydroamination of terminal alkynes: Water-triggered chemo- and regioselective synthesis of fused tricyclic xanthines

Advanced Synthesis and Catalysis

Volumn 351, Issue 17, 2009, Pages 2770-2778

  Ye, Deju ^a   Zhang, Xu ^a,b   Zhou, Yu ^a   Zhang, Dengyou ^a   Zhang, Lei ^a   Wang, Hengshuai ^a   Jiang, Hualiang ^a,c   Liu, Hong ^a  

^a SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

^b CHINA PHARMACEUTICAL UNIVERSITY   (China)

^c EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

Gold; Hydroamination; Silver; Terminal alkynes; Xanthines

Indexed keywords

EID: 72149120834     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200900505     Document Type: Article

References (59)

1. J. W. Daly, Cell. Mol. Life Sci. 2007, 64, 2153-2169.
2. L. Maia, A. de Mendonga, Eur. J. Neurol. 2002, 9, 377-382.
3. R. J. Stine, R. H. Marcus, C. A. Parvin, Ann. Emerg. Med. 1989, 18, 640-646.
4. P. Cui, T. L. Macdonald, M. Chen, J. L. Nadler, Bioorg. Med. Chem. Lett. 2006, 16, 3401-3405.
5. J. Hockemeyer, J. C. Burbiel, C. E. Müller, J. Org. Chem. 2004, 69, 3308-3318.
6. Y-P. Lu, Y-R. Lou, J-G. Xie, Q-Y. Peng, S. Zhou, Y. Lin, W. J. Shih, A. H. Conney, Carcinogenesis 2007, 28, 199-206.
7. a) K. Kiec-Kononowicz, A. Drabczynska, E. Pekala, B. Michalak, C. E. Müller, B. Schumacher, J. Karolak-Wojciechowska, H. Duddeck, S. Rockitt, R. Wartchow, Pure Appl. Chem. 2001, 73, 1411-1420;
8. b) A. Drabczynska, B. Schumacher, C. E. Müller, J. Karolak-Wojciechowska, B. Michalak, E. Pekala, K. Kiec-Kononowicz, Eur. J. Med. Chem. 2003, 38, 397-402.
9. a) S. Rockitt, H. Duddeck, A. Drabczynska, K. KiecKononowicz. Eur. J. Org. Chem. 2000, 3489-3496;
10. b) S. Rockitt, R. Wartchow, H. Duddeck, A. Drabczyńska, K. Kieć-Kononowicz, Z. Naturforsch. 2001, 56b, 319-324.
11. For recent reviews, see: a) J. M. Lee, Y. Na, H. Han, S. Chang, Chem. Soc. Rev. 2004, 33, 302-312;
12. b) A. Ajamian, J. L. Gleason, Angew. Chem. 2004, 776, 3842-3848;
13. Angew. Chem. Int. Ed. 2004, 43, 3754-3760;
14. c)XC. Wasilke, S. J. Obrey, R. T. Baker, G. C. Bazan, Chem. Rev. 2005, 105, 1001-1020;
15. d)A. deMeijere, P. von Zezschwitz, S. Brise, Acc. Chem. Res. 2005, 38, 413-422;
16. e) A. S. K. Hashmi, Chem. Rev. 2007, 107, 3180-3211;
17. f) Z-G. Li, G. Brouwer, C. He, Chem. Rev. 2008, 108, 3239-3265;
18. g) H. C. Shen, Tetrahedron 2008, 64, 3885-3903.
19. a) A. Arcadi, G. Bianchi, F. Marinelli, Synthesis 2004, 610-618;
20. b) I. Nakamura, U. Yamagishi, D. Song, S. Konta, Y. Yamamoto, Angew. Chem. 2007, 119, 2334;
21. Angew. Chem. Int. Ed. 2007, 46, 2284;
22. c)Y. Zhang, J. P. Donahue, C.-J. Li, Org. Lett. 2007, 9, 627.
23. a) D. J. Gorin, N. R. Davis, F. D. Toste, J. Am. Chem. Soc. 2005, 127, 11260;
24. b) N. Morita, N. Krause, Org. Lett. 2004, 6, 4121;
25. c)F.M. Istrate, F. Gagose, Org. Lett. 2007, 9, 3181-3184.
26. X-Y. Liu, P. Ding, J-S. Huang, C-M. Che, Org. Lett. 2007, 9, 2645-2648.
27. Q. P. Ding, Y. Ye, R. H. Fan, J. Wu, J. Org. Chem. 2007, 72, 5439-5442.
28. D. J. Ye, J. F. Wang, X. Zhang, Y. Zhou, X. Ding, E. G. Feng, H. F. Sun, G. N. Liu, H. L. Jiang, H. Liu, Green Chem. 2009, 11, 1201-1208.
29. a) Z. G. Li, H. B. Sun, H. L. Jiang, H. Liu, Org. Lett. 2008, 10, 3263-3266;
30. b) E. G. Feng, H, Huang, Y. Zhou, D. J. Ye, H. L. Jiang, H. Liu, J. Org. Chem. 2009, 74, 2846-2849.
31. For the synthesis of 8-(but-3-ynyl)-xanthines 1, see: a) H. O. Kim, X-D. Ji, N. Melman, M. E. Olah, G. L. Stiles, K. A. Jacobson, J. Med. Chem. 1994, 37, 3373-3382;
32. b) P. G. Baraldi, M. A. Tabrizi, D. Preti, A. Bovero, R. Romagnoli, F. Fruttarolo, N. A. Zaid, A. R. Moorman, K. Varani, S. Gessi, S. Merighi, P. A. Borea, J. Med. Chem. 2004, 47,1434-1447.
33. CCDC 737104 and CCDC 737105 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.ca-rn.ac.uk/data-request/ cif.
34. For water-triggered reaction, see: a) X. Yao, C.-J. Li, Org. Lett. 2005, 7, 4395-4398;
35. b) X. Yao, C.-J. Li, Org. Lett. 2006, 8, 1953-1955;
36. c)M. Yu, R. Skouta, L. Zhou, H-F. Jiang, X. Yao, C.-J. Li, J. Org. Chem. 2009, 74, 3378-3383.
37. Water often exhibits an unprecedented effect on the rate and selectivity of organic reactions through hydrophobic interactions and the enrichment of organic substrates in the local hydrophobic environment, see a) C I. Herrerías, X. Yao, Z. Li, C.-J. Li, Chem. Rev. 2007, 107, 2546-2562;
38. b) R. Breslow, Acc. Chem. Res. 2004, 37, 471-478;
39. c)U. M. Lindström, F. Andersson, Angew. Chem. 2006, 118, 562-565;
40. Angew. Chem. Int. Ed. 2006, 45, 548-551;
41. X-Y. Liu, C-M. Che, Angew. Chem. 2008, 120, 3865-3870;
42. Angew. Chem. Int. Ed. 2008, 47, 3805-3810.
43. For reviews on vinylidene complexes, see: a) C. Bruneau, P.H. Dixneuf, Ace. Chem. Res. 1999, 32, 311-323;
44. b) B. M. Trost, A. McClory, Chem. Asian J. 2008, 3, 164-194;
45. c)F. E. McDonald, Chem. Eur. J. 1999, 5, 3103-3106. For synthetic use of vinylidene intermediates, see for examples:
46. d)I. V. Seregin, V. Gevorgyan, J. Am. Chem. Soc. 2006, 128, 12050-12051;
47. e) V. Mamane, P. Hannen, A. Fürstner, Chem. Eur. J. 2004, 10, 4556-4575;
48. f) K. Maeyama, N. Iwasawa, J. Am. Chem. Soc. 1998, 120, 1928-1928;
49. g) N. Iwasawa, K. Maeyama, H. Kusama, Org. Lett. 2001, 3, 3871-3873;
50. h) H. Kusama, H. Yamabe, N. Iwasawa, Org. Lett. 2002, 4, 2569-2751;
51. i)N. Iwasawa, M. Shido, K. Maeyama, H Kusama, J. Am. Chem. Soc. 2000, 122, 10226-11027;
52. j) T. Miura, N. Iwasawa, J. Am. Chem. Soc. 2002, 124, 518-519;
53. k) K. Miki, F. Nishino, K. Ohe, S. Uemura, J. Am. Chem. Soc. 2002, 124, 5260-5267.
54. 6 under optimal conditions. "chemical equation presented"
55. J. Barluenga, A. Diéguez, A. Fernández, F. Rodríguez, F.J. Fañanás, Angew. Chem. 2006, 118, 2145-2147;
56. Angew. Chem. Int. Ed. 2006, 45, 2091-2093.
57. 2]-3a was also probable.
58. a) R. Lok, R. E. Leone, A. J. Williams, J. Org. Chem. 1996, 61, 3289-3297;
59. b) T. Godet, C. Vaxelaire, C. Michel, A. Milet, P. Belmont, Chem. Eur. J. 2007, 13, 5632-5641.