Access to functionalized isoquinoline N-oxides via sequential electrophilic cyclization/cross-coupling reactions

Advanced Synthesis and Catalysis

Volumn 350, Issue 11-12, 2008, Pages 1850-1854

  Ding, Qiuping ^a,c   Wu, Jie ^a,b  

^a FUDAN UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^c JIANGXI NORMAL UNIVERSITY   (China)

Author keywords

2 alkynylbenzaldoximes; Cross coupling reaction; Electrophilic cyclization; Isoquinoline N oxides

Indexed keywords

EID: 53849138392     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200800301     Document Type: Article

References (66)

1. a) D. P. Walsh, Y.-T. Chang, Chem. Rev. 2006, 106, 2476;
2. b) P. Arya, D. T. H. Chou, M.-G. Baek, Angew. Chem. 2001, 113, 351;
3. Angew. Chem. Int. Ed. 2001, 40, 339;
4. c) S. L. Schreiber, Science 2000, 287, 1964.
5. K. W. Bentley, The Isoquinoline Alkaloids, Harwood Academic, Australia, 1998, Vol. 1.
6. For selected examples, see: a) M. Nakajima, M. Saito, M. Shiro, S.-I. Hashimoto, J. Am. Chem. Soc. 1998, 120, 6419;
7. b) T. Shimada, A. Kina, S. Ikeda, T. Hayashi, Org. Lett. 2002, 4, 2799;
8. c) A. V. Malkov, M. Orsini, D. Pernazza, K. W. Muir, V. Langer, P. Meghani, P. Kočovský, Org. Lett. 2002, 4, 1047;
9. d) A. V. Malkov, L. Dufkova, L. Farrugia, P. Kočovský, Angew. Chem. 2003, 115, 3802;
10. Angew. Chem. Int. Ed. 2003, 42, 3674;
11. e) R. Hrdina, I. Valterová, J. Hodačová, I. Císařová, M. Kotora, Adv. Synth. Catal. 2007, 349, 822.
12. a) D. Collado, E. Perez-Inestrosa, R. Suau, J. Org. Chem. 2003, 68, 3574;
13. b) D. Collado, E. Perez-Inestrosa, R. Suau, J.-P. Desvergne, H. Bouas-Laurent, Org. Lett. 2002, 4, 855;
14. c) D. Collado, E. Perez-Inestrosa, R. Suau, J. T. L. Navarrete, Tetrahedron 2006, 62, 2927;
15. d) Y. Y. Durmaz, G. Yilmaz, Y. Yagci, J. Polym. Sci., Part A.: Polym. Chem. 2007, 45, 423.
16. 2 as stoichiometric oxidant, see: a) C. Copéret, H. Adolfsson, J. P. Chiang, A. K. Yudin, K. Sharpless, J. Org. Chem. 1998, 63, 1740;
17. b) M. R. Prasad, G. Kamalakar, G. Madhavi, S. J. Kulkarni, K. V. Raghavan, Chem. Commun. 2000, 1577.
18. a) H.-S. Yeom, S. Kim, S. Shin, Synlett 2008, 924;
19. b) T. Sakamoto, Y. Kondo, N. Miura, K. Hayashi, H. Yamanaka, Heterocycles 1986, 24, 2311.
20. For selected examples, see: a) R. C. Larock, in: Acetylene Chemistry, (Eds.: F. Diederich, P. J. Stang, R. R. Tykwinski), Wiley-VCH, Weinheim, 2005, pp 51-99;
21. b) F. Alonso, I. P. Beletskaya, M. Yus, Chem. Rev. 2004, 104, 3079;
22. c) G. Zeni, R. C. Larock, Chem. Rev. 2006, 106, 4644.
23. For selected examples, see: a) Q. Ding, J. Wu, Org. Lett. 2007, 9, 4959;
24. b) K. Gao, J. Wu, J. Org. Chem. 2007, 72, 8611;
25. c) W. Sun, Q. Ding, X. Sun, R. Fan, J. Wu, J. Comb. Chem. 2007, 9, 690;
26. d) Y. Ye, Q. Ding, J. Wu, Tetrahedron 2008, 64, 1378.
27. a) S. Obika, H. Kono, Y. Yasui, R. Yanada, Y. Takemoto, J. Org. Chem. 2007, 72, 4462, and references cited therein;
28. b) N. Asao, S. Yudha S., T. Nogami, Y. Yamamoto, Angew. Chem. 2005, 117, 5662;
29. Angew. Chem. Int. Ed. 2005, 44, 5526;
30. c) R. Yanada, S. Obika, H. Kono, Y. Takemoto, Angew. Chem. 2006, 118, 3906;
31. Angew. Chem. Int. Ed. 2006, 45, 3822;
32. d) N. Asao, K. Iso, S. Yudha, Org. Lett. 2006, 8, 4149;
33. e) N. Asao, C. S. Chan, K. Takahashi, Y. Yamamoto, Tetrahedron 2005, 61, 11322;
34. f) M. Ohtaka, H. Nakamura, Y. Yamamoto, Tetrahedron Lett. 2004, 45, 7339;
35. g) B. Witulski, C. Alayrac, L. Tevzadze-Saeftel, Angew. Chem. 2003, 115, 4392;
36. Angew. Chem. Int. Ed. 2003, 42, 4257;
37. h) I. Yavari, M. Ghazanfarpour-Darjani, M. Sabbaghan, Z. Hossaini, Tetrahedron Lett. 2007, 48, 3749;
38. i) A. Shaabani, E. Soleimani, H. R. Khavasi, Tetrahedron Lett. 2007, 48, 4743;
39. j) G.-W. Wang, J.-X. Li, Org. Biomol. Chem. 2006, 4, 4063;
40. k) J. L. Diaz, M. Miguel, R. Lavilla, J. Org. Chem. 2004, 69, 3550.
41. a) Q. Huang, R. C. Larock, J. Org. Chem. 2003, 68, 980;
42. b) G. Dai, R. C. Larock, J. Org. Chem. 2003, 68, 920;
43. c) G. Dai, R. C. Larock, J. Org. Chem. 2002, 67, 7042;
44. d) Q. Huang, J. A. Hunter, R. C. Larock, J. Org. Chem. 2002, 67, 3437;
45. e) K. R. Roesch, R. C. Larock, J. Org. Chem. 2002, 67, 86;
46. f) K. R. Roesch, H. Zhang, R. C. Larock, J. Org. Chem. 2001, 66, 8042;
47. g) K. R. Roesch, R. C. Larock, Org. Lett. 1999, 1, 553.
48. For selected examples, see: a) H.-P. Bi, L.-N. Guo, X.-H. Duan, F.-R. Gou, S.-H. Huang, X.-Y. Liu, Y.-M. Liang, Org. Lett. 2007, 9, 397;
49. b) A. Sniady, K. A. Wheeler, R. Dembinski, Org. Lett. 2005, 7, 1769;
50. c) Y.-H. Liu, F.-J. Song, L. Q. Cong, J. Org. Chem. 2005, 70, 6999;
51. d) A. Y. Peng, Y. X. Ding, Org. Lett. 2004, 6, 1119;
52. e) D. Yue, T. Yao, R. C. Larock, J. Org. Chem. 2005, 70, 10292;
53. f) B. L. Flynn, P. Verdier-Pinard, E. Hamel, Org. Lett. 2001, 3, 651;
54. g) D. Yue, R. C. Larock, J. Org. Chem. 2002, 67, 1905;
55. h) K. O. Hessian, B. L. Flynn, Org. Lett. 2003, 5, 4377;
56. i) A. Arcadi, S. Cacchi, S. D. Giuseppe, G. Fabrizi, F. Marinelli, Org. Lett. 2002, 4, 2409;
57. j) Q. Huang, J. A. Hunter, R. C. Larock, J. Org. Chem. 2002, 67, 3437;
58. k) T. Yao, R. C. Larock, J. Org. Chem. 2003, 68, 5936;
59. l) T. Yao, M. A. Campo, R. C. Larock, Org. Lett. 2004, 6, 2677;
60. m) D. Yue, C. N. Della, R. C. Larock, Org. Lett. 2004, 6, 1581;
61. n) T. Yao, R. C. Larock, J. Org. Chem. 2005, 70, 1432;
62. o) J. Barluenga, M. Trincado, M. Marco-Arias, A. Ballesteros, E. Rubio, J. M. Gonzalez, Chem. Commun. 2005, 2008;
63. p) D. Fischer, H. Tomeba, N. K. Pahadi, N. T. Patil, Y. Yamamoto Angew. Chem. 2007, 119, 4848;
64. Angew. Chem. Int. Ed. 2007, 46, 4764;
65. q) Y.-X. Xie, X.-Y. Liu, L.-Y. Wu Y. Han, L.-B. Zhao, M.-J. Fan, Y.-M. Liang Eur. J. Org. Chem. 2008, 1013.
66. S. H. Yang, S. Chang, Org. Lett. 2001, 3, 4209.