Tandem electrophilic cyclization-[3+2] cycloaddition-rearrangement reactions of 2-alkynylbenzaldoxime, DMAD, and Br2

Journal of Organic Chemistry

Volumn 74, Issue 2, 2009, Pages 921-924

  Ding, Qiuping ^a   Wang, Zhiyong ^a   Wu, Jie ^a,b  

^a FUDAN UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AZOMETHINE YLIDES; ELECTROPHILIC CYCLIZATION; FUNCTIONALIZED; ISOQUINOLINE; PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS; REARRANGEMENT REACTIONS;

BROMINE; PALLADIUM;

CYCLIZATION;

2 ALKYNYLBENZALDOXIME; ALKYNE; ALKYNYL GROUP; AZOMETHINE YLIDE; BROMIDE; CARBOXYLIC ACID DERIVATIVE; DIMETHYL ACETYLENE DICARBOXYLATE; ELECTROPHILE; IODINE; ISOQUINOLINE; NITROGEN; OXYGEN; PALLADIUM; PHOSPHORUS; SULFUR; UNCLASSIFIED DRUG; ACETYLENEDICARBOXYLIC ACID DIMETHYL ESTER; BROMINE; ISOQUINOLINE DERIVATIVE; OXIME; TRANSITION ELEMENT;

ARTICLE; CATALYSIS; CROSS COUPLING REACTION; CYCLIZATION; CYCLOADDITION; REACTION ANALYSIS; CHEMISTRY;

ALKYNES; BROMINE; CATALYSIS; CYCLIZATION; ISOQUINOLINES; OXIMES; TRANSITION ELEMENTS;

EID: 60849087693     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo802076k     Document Type: Article

References (83)

1. (1)(a) Walsh, D. P.; Chang, Y.-T. Chem. Rev. 2006, 106, 2476.
2. (b) Arya, P.; Chou, D. T. H.; Baek, M.-G. Angew. Chem., Int. Ed. 2001, 40, 339.
3. (c) Schreiber, S. L. Science 2000, 287, 1964.
4. For selected examples, see: (a) Denmark, S. E.; Thorarensen, A. Chem. Rev. 1996, 96, 137.
5. (b) Porco, J. A., Jr.; Schoenen, F. J.; Stout, T. J.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1990, 112, 7410.
6. (c) Molander, G. A.; Harris, C. R. J. Am. Chem. Soc. 1996, 118, 4059.
7. (d) Chen, C.; Layton, M. E.; Sheehan, S. M.; Shair, M. D. J. Am. Chem. Soc. 2000, 122, 7424.
8. (e) Shi, F.; Li, X.; Xia, Y.; Zhang, L.; Yu, Z.-X. J. Am. Chem. Soc. 2007, 129, 15503.
9. For selected examples, see: (a) Bentley, K. W. The Isoquinoline Alkaloids: Harwood Academic: Amsterdam, The Netherlands, 1998; Vol. 1.
10. (b) Trotter, B. W.; Nanda, K. K.; Kett, N. R.; Regan, C. P.; Lynch, J. J.; Stump, G. L.; Kiss, L.; Wang, J.; Spencer, R. H.; Kane, S. A.; White, R. B.; Zhang, R.; Anderson, K. D.; Liverton, N. J.; Mclntyre, C. J.; Beshore, D. C.; Hartman, G. D.; Dinsmore, C. J. J. Med. Chem. 2006, 49, 6954.
11. (c) Ramesh, P.; Reddy, N. S.; Venkateswarlu, Y. J. Nat. Prod. 1999, 62, 780.
12. (d) Oi, S.; Ikedou, K.; Takeuchi, K.; Ogino, M.; Banno, Y.; Tawada, H.; Yamane, T. PCT Int. Appl. 2002, 600. pp (WO 2002062764 A1).
13. (e) Kaneda, T.; Takeuchi, Y.; Matsui, H.; Shimizu, K.; Urakawa, N.; Nakajyo, S. J. Pharmacol. Sci. 2005, 98, 275.
14. (f) Mikami, Y.; Yokoyama, K.; Tabeta, H.; Nakagaki, K.; Arai, T. J. Pharm. Dyn. 1981, 4, 282.
15. (g) Marchand, C.; Antony, S.; Kohn, K. W.; Cushman, M.; Ioanoviciu, A.; Staker, B. L.; Burgin, A. B.; Stewart, L.; Pommier, Y. Mol. Cancer Ther. 2006, 5, 287.
16. (h) Pettit, G. R.; Gaddamidi, V.; Herald, D. L.; Singh, S. B.; Cragg, G. M.; Schmidt, J. M.; Boettner, F. E.; Williams, M.; Sagawa, Y. J. Nat. Prod. 1986, 49, 995.
17. (a) Obika, S.; Kono, H.; Yasui, Y.; Yanada, R.; Takemoto, Y. J. Org. Chem. 2007, 72, 4462, and references cited therein.
18. (b) Asao, N.; Yudha S, S.; Nogami, T.; Yamamoto, Y. Angew. Chem., Int. Ed. 2005, 44, 5526.
19. (c) Yanada, R.; Obika, S.; Kono, H.; Takemoto, Y. Angew. Chem., Int. Ed. 2006, 45, 3822.
20. (d) Asao, N.; Iso, K.; Yudha, S. S. Org. Lett. 2006, 8, 4149.
21. (e) Mori, S.; Uerdingen, M.; Krause, N.; Morokuma, K. Angew. Chem., Int. Ed. 2005, 44, 4715.
22. (f) Asao, N.; Chan, C. S.; Takahashi, K.; Yamamoto, Y. Tetrahedron 2005, 61, 11322.
23. (g) Ohtaka, M.; Nakamura, H.; Yamamoto, Y. Tetrahedron Lett. 2004, 45, 7339.
24. (h) Witulski, B.; Alayrac, C.; Tevzadze-Saeftel, L. Angew. Chem., Int. Ed. 2003, 42, 4257.
25. (i) Yavari, I.; Ghazanfarpour-Darjani, M.; Sabbaghan, M.; Hossaini, Z. Tetrahedron Lett. 2007, 48, 3749.
26. (j) Shaabani, A.; Soleimani, E.; Khavasi, H. R. Tetrahedron Lett. 2007, 48, 4743.
27. (k) Wang, G.-W.; Li, J.-X. Org. Biomol. Chem. 2006, 4, 4063.
28. (l) Diaz, J. L.; Miguel, M.; Lavilla, R. J. Org. Chem. 2004, 69, 3550.
29. (a) Huang, Q.; Larock, R. C. J. Org. Chem. 2003, 68, 980.
30. (b) Dai, G.; Larock, R. C. J. Org. Chem. 2003, 68, 920.
31. (c) Dai, G.; Larock, R. C. J. Org. Chem. 2002, 67, 7042.
32. (d) Huang, Q.; Hunter, J. A.; Larock, R. C. J. Org. Chem. 2002, 67, 3437.
33. (e) Roesch, K. R.; Larock, R. C. J. Org. Chem. 2002, 67, 86.
34. (f) Roesch, K. R.; Zhang, H.; Larock, R. C. J. Org. Chem. 2001, 66, 8042.
35. (g) Roesch, K. R.; Larock, R. C. Org. Lett. 1999, 1, 553.
36. (6)(a) Ding, Q.; Wu, J. Org. Lett. 2007, 9, 4959.
37. (b) Gao, K.; Wu, J. J. Org. Chem. 2007, 72, 8611.
38. (c) Ding, Q.; Ye, Y.; Fan, R.;Wu, J. J. Org. Chem. 2007, 72, 5439.
39. (d) Sun, W.; Ding, Q.; Sun, X.; Fan, R.; Wu, J. J. Comb. Chem. 2007, 9, 690.
40. (e) Ye, Y.; Ding, Q.; Wu, J. Tetrahedron 2008, 64, 1378.
41. (f) Ding, Q.; Yu, X.; Wu, J. Tetrahedron Lett. 2008, 49, 2752.
42. (g) Ding, Q.; Wang, B.; Wu, J. Tetrahedron 2007, 63, 12166.
43. (7)(a) Ding, Q.; Wu, J. Adv. Synth. Catal. 2008, 350, 1850.
44. (b) Gao, K.; Wu, J. Org. Lett. 2008, 10, 2251.
45. (c) Ding, Q.; Wu, J. J. Comb. Chem. 2008, 10, 541.
46. (d) Wang, Z.; Fan, R.; Wu, J. Adv. Synth. Catal. 2007, 349, 1943.
47. (e) Zhang, L.; Wu, J. Adv. Synth. Catal. 2007, 349, 1047.
48. For selected examples, see: (a) Bi, H.-P.; Guo, L.-N.; Duan, X.-H.; Gou, F.-R.; Huang, S.-H.; Liu, X.-Y.; Liang, Y.-M. Org. Lett. 2007, 9, 397.
49. (b) Sniady, A.; Wheeler, K. A.; Dembinski, R. Org. Lett. 2005, 7, 1769.
50. (c) Liu, Y.-H.; Song, F.-J.; Cong, L. Q. J. Org. Chem. 2005, 70, 6999.
51. (d) Peng, A. Y.; Ding, Y. X. Org. Lett. 2004, 6, 1119.
52. (e) Yue, D.; Yao, T.; Larock, R. C. J. Org. Chem. 2005, 70, 10292.
53. (f) Flynn, B. L.; Verdier-Pinard, P.; Hamel, E. Org. Lett. 2001, 3, 651.
54. (g) Yue, D.; Larock, R. C. J. Org. Chem. 2002, 67, 1905.
55. (h) Hessian, K. O.; Flynn, B. L. Org. Lett. 2003, 5, 4377.
56. (i) Arcadi, A.; Cacchi, S.; Giuseppe, S. D.; Fabrizi, G.; Marinelli, F. Org. Lett. 2002, 4, 2409.
57. (j) Huang, Q.; Hunter, J. A.; Larock, R. C. J. Org. Chem. 2002, 67, 3437.
58. (k) Yao, T.; Larock, R. C. J. Org. Chem. 2003, 68, 5936.
59. (l) Yao, T.; Campo, M. A.; Larock, R. C. Org. Lett. 2004, 6, 2677.
60. (m) Yue, D.; Della, C. N.; Larock, R. C. Org. Lett. 2004, 6, 1581.
61. (n) Yao, T.; Larock, R. C. J. Org. Chem. 2005, 70, 1432.
62. (o) Barluenga, J.; Trincado, M.; Marco-Arias, M.; Ballesteros, A.; Rubio, E.; Gonzalez, J. M. Chem. Commun. 2005, 2008.
63. For reviews, see: (a) Larock, R. C. In Acetylene Chemistry;Diederich, F., Stang, P. J., Tykwinski, R. R., Eds.; Wiley-VCH: Weinheim, Germany, 2005; pp 51-99.
64. (b) Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2004, 104, 3079.
65. (c) Zeni, G.; Larock, R. C. Chem. Rev. 2006, 106, 4644.
66. Selected examples for metal-catalyzed cyclization of 2-alkynylbenzal- dehyde: (a) Beeler, A. B.; Su, S.; Singleton, C. A.; Porco, J. A., Jr. J. Am. Chem. Soc. 2007, 129, 1413, and references cited therein.
67. (b) Asao, N. Synlett 2006, 1645.
68. (c) Nakamura, I.; Mizushima, Y.; Gridnev, I. D.; Yamamoto, Y. J. Am. Chem. Soc. 2005, 127, 9844.
69. (d) Kim, N.; Kim, Y.; Park, W.; Sung, D.; Gupta, A.-K.; Oh, C.-H. Org. Lett. 2005, 7, 5289.
70. (e) Sato, K.; Asao, N.; Yamamoto, Y. J. Org. Chem. 2005, 70, 8977.
71. (f) Asao, N.; Sato, K.; Menggenbateer; Yamamoto, Y. J. Org. Chem. 2005, 70, 3682.
72. (g) Kusama, H.; Funami, H.; Takaya, J.; Iwasawa, N. Org. Lett. 2004, 6, 605.
73. (h) Asao, N.; Aikawa, H.; Yamamoto, Y. J. Am. Chem. Soc. 2004, 126, 7459.
74. (i) Asao, N.; Aikawa, H.; Yamamoto, Y. J. Am. Chem. Soc. 2004, 126, 7458.
75. For reviews, see: (a) Husinec, S.; Savic, V. Tetrahedron: Asymmetry 2005, 16, 2047.
76. (b) Kanemasa, S. Synlett 2002, 1371.
77. (c) Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863.
78. (d) Pichon, M.; Figadere, B. Tetrahedron: Asymmetry 1996, 7, 927.
79. We thank the referee's helpful suggestion for structure identification of compound 2.
80. Coskun, N.: Tuncman, S. Tetrahedron 2006, 62 1345.
81. For recent reviews, see: (a) Miyaura, N. Top. Curr. Chem. 2002, 219, 11.
82. (b) Suzuki, A. J. Organomet. Chem. 1999, 576, 147.
83. (c) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176.