Procedure-controlled selective synthesis of 5-acyl-2-iminothiazolines and their selenium and tellurium derivatives by convergent tandem annulation

Angewandte Chemie - International Edition

Volumn 50, Issue 35, 2011, Pages 8122-8126

  Wang, Yang ^a   Zhang, Wen Xiong ^a,b   Wang, Zitao ^a   Xi, Zhenfeng ^a  

^a PEKING UNIVERSITY   (China)

^b NANKAI UNIVERSITY   (China)

Author keywords

1,5 acyl migration; cyclization; heterocycles; selenium; tellurium

Indexed keywords

1,5-ACYL MIGRATION; ACID CHLORIDES; CARBODIIMIDES; CHALCOGEN ELEMENTS; HETEROCYCLES; SELECTIVE SYNTHESIS; TERMINAL ALKYNE; TITLE COMPOUNDS;

ACETYLENE; CHLORINE COMPOUNDS; SELENIUM; TELLURIUM; TELLURIUM COMPOUNDS;

SELENIUM COMPOUNDS;

EID: 80051715539     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201101948     Document Type: Article

References (97)

1. R. M. Moslin, T. F. Jamison, J. Am. Chem. Soc. 2006, 128, 15106
2. I. Larrosa, M. I. D. Silva, P. M. Gómez, P. Hannen, E. Ko, S. R. Lenger, S. R. Linke, A. J. P. White, D. Wilton, A. G. M. Barrett, J. Am. Chem. Soc. 2006, 128, 14042
3. M. Hirama, T. Oishi, H. Uehara, M. Inoue, M. Maruyama, H. Oguri, M. Satake, Science 2001, 294, 1904
4. L. A. Paquette, L Barriault, D. Pissarnitski, J. Am. Chem. Soc. 1999, 121, 4542
5. D. Sames, X. T. Chen, S. J. Danishefsky, Nature 1997, 389, 587
6. K. C. Nicolaou, Z. Yang, J. J. Liu, H. Ueno, P. G. Nantermet, R. K. Guy, C. F. Clalborne, J. Renaud, E. A. Couladouros, K. Paulvannan, E. J. Sorensen, Nature 1994, 367, 630.
7. Multicomponent Reactions (Eds.:, J. Zhu, H. Bienayme,), Wiley-VCH, Weinheim, 2005
8. J. Zhu, Eur. J. Org. Chem. 2003, 1133
9. A. Jacobi von Wangelin, H. Neumann, D. Gördes, S. Klaus, D. Strübing, M. Beller, Chem. Eur. J. 2003, 9, 4286; for reviews of tandem reactions, see
10. S. E. Denmark, A. Thorarensen, Chem. Rev. 1996, 96, 137
11. J.-C. Wasilke, S. J. Obrey, R. T. Baker, G. C. Bazan, Chem. Rev. 2005, 105, 1001
12. C. Grondal, M. Jeanty, D. Enders, Nat. Chem. 2010, 2, 167.
13. G. Wu, X. L. Qiu, L. Zhou, J. Zhu, R. Chamberlin, J. Lau, P. L. Chen, W. H. Lee, Cancer Res. 2008, 68, 8393
14. M. Tomizawa, S. Kagabu, I. Ohno, K. A. Durkin, J. E. Casida, J. Med. Chem. 2008, 51, 4213
15. T. Shimamura, J. Shibata, H. Kurihara, T. Mita, S. Otsuki, T. Sagara, H. Hirai, Y. Iwasawa, Bioorg. Med. Chem. Lett. 2006, 16, 3751
16. J. R. Lewis, Nat. Prod. Rep. 1999, 16, 389.
17. I. Ohno, M. Tomizawa, K. A. Durkin, Y. Naruse, J. E. Casida, S. Kagabu, Chem. Res. Toxicol. 2009, 22, 476
18. H. Ohta, T. Ishizaka, M. Tatsuzuki, M. Yoshinaga, I. Iida, Y. Tomishima, Y. Toda, S. Saito, Bioorg. Med. Chem. Lett. 2007, 17, 6299
19. A. Manaka, M. Sato, M. Aoki, M. Tanaka, T. Ikeda, Y. Toda, Y. Yamane, S. Nakaike, Bioorg. Med. Chem. Lett. 2001, 11, 1031.
20. Q. Zhao, C. Shen, H. Zheng, J. Zhang, P. Zhang, Carbohydr. Res. 2010, 345, 437
21. C. Roussel, N. Vanthuyne, M. Bouchekara, A. Djafri, J. Elguero, I. Alkorta, J. Org. Chem. 2008, 73, 403
22. S. Murru, C. B. Singh, V. Kavala, B. K. Patel, Tetrahedron 2008, 64, 1931
23. L. Gomez, F. Gellibert, A. Wagner, C. Mioskowski, Tetrahedron Lett. 2008, 49, 2726
24. C. B. Singh, S. Murru, V. Kavala, B. K. Patel, Org. Lett. 2006, 8, 5397
25. A. Manaka, T. Ishii, K. Takahashi, M. Sato, Tetrahedron Lett. 2005, 46, 419
26. S. Bae, H. G. Hahn, K. D. Nam, J. Comb. Chem. 2005, 7, 7
27. S. Bae, H. G. Hahn, K. D. Nam, J. Comb. Chem. 2005, 7, 826
28. N. De Kimpe, M. Boelens, J. P. Declercq, Tetrahedron 1993, 49, 3411.
29. T. E. Glotova, M. Y. Dvorko, A. I. Albanov, O. N. Kazheva, G. V. Shilov, O. A. D'yachenko, Russ. J. Org. Chem. 2008, 44, 1532.
30. M. D'hooghe, A. Waterinckx, N. De Kimpe, J. Org. Chem. 2005, 70, 227.
31. Y. Sanemitsu, S. Kawamura, J. Satoh, T. Katayama, S. Hashimoto, J. Pestic. Sci. 2006, 31, 305.
32. Z. Wang, Y. Wang, W. X. Zhang, Z. Hou, Z. Xi, J. Am. Chem. Soc. 2009, 131, 15108.
33. C. J. Li, Acc. Chem. Res. 2010, 43, 581
34. S. H. Kim, S. Chang, Org. Lett. 2010, 12, 1868
35. M. Nishiura, Z. Hou, Bull. Chem. Soc. Jpn. 2010, 83, 595
36. W. X. Zhang, M. Nishiura, Z. Hou, Angew. Chem. 2008, 120, 9846
37. Angew. Chem. Int. Ed. 2008, 47, 9700
38. I. Bae, H. Han, S. Chang, J. Am. Chem. Soc. 2005, 127, 2038
39. C. Wei, J. T. Mague, C. J. Li, Proc. Natl. Acad. Sci. USA 2004, 101, 5749
40. M. Nishiura, Z. Hou, Y. Wakatsuki, T. Yamaki, T. Miyamoto, J. Am. Chem. Soc. 2003, 125, 1184
41. D. E. Frantz, R. Fässler, C. S. Tomooka, E. M. Carreira, Acc. Chem. Res. 2000, 33, 373; for the preparation of lithium alkynethiolate, see
42. N. Miyaura, T. Yanagi, A. Suzuki, Chem. Lett. 1979, 535
43. L. Brandsma, Preparative Acetylenic Chemistry, 2 nd ed., Elsevier, Amsterdam, 1988
44. W. R. Förster, R. Isecke, C. Spanka, E. Schaumann, Synthesis 1997, 942
45. H. Sugiyama, Y. Hayashi, H. Kawaguchi, K. Tatsumi, Inorg. Chem. 1998, 37, 6773.
46. Until recently, 5-acyl-2-iminoselenazoline was unknown and only one report on the synthesis of 2-iminoselenazoline by the Hantzsch condensation reaction was found, see:, P. K. Atanassov, A. Linden, H. Heimgartmer, Helv. Chim. Acta 2010, 93, 395.
47. H. Shen, Z. Xie, J. Organomet. Chem. 2009, 694, 1652
48. W. X. Zhang, Z. Hou, Org. Biomol. Chem. 2008, 6, 1720
49. F. T. Edelmann, Adv. Organomet. Chem. 2008, 57, 183
50. M. P. Coles, Dalton Trans. 2006, 985
51. P. J. Bailey, S. Pace, Coord. Chem. Rev. 2001, 214, 91
52. J. Barker, M. Kilner, Coord. Chem. Rev. 1994, 133, 219
53. A. Williams, I. T. Ibrahim, Chem. Rev. 1981, 81, 589.
54. R. T. Yu, T. Rovis, J. Am. Chem. Soc. 2008, 130, 3262
55. A. Volonterio, M. Zanda, Org. Lett. 2007, 9, 841
56. T. Saito, K. Sugizaki, T. Otani, T. Suyama, Org. Lett. 2007, 9, 1239
57. X. Xu, D. Cheng, J. Li, H. Guo, J. Yan, Org. Lett. 2007, 9, 1585
58. H. Li, J. L. Petersen, K. K. Wang, J. Org. Chem. 2003, 68, 5512
59. M. Schmittel, D. Rodríguez, J. P. Steffen, Angew. Chem. 2000, 112, 2236
60. Angew. Chem. Int. Ed. 2000, 39, 2152.
61. D. Li, J. Guang, W. X. Zhang, Y. Wang, Z. Xi, Org. Biomol. Chem. 2010, 8, 1816
62. W. X. Zhang, D. Li, Z. Wang, Z. Xi, Organometallics 2009, 28, 882
63. W. X. Zhang, M. Nishiura, T. Mashiko, Z. Hou, Chem. Eur. J. 2008, 14, 2167
64. M. R. Crimmin, A. G. M. Barrett, M. S. Hill, P. B. Hitchcock, P. A. Procopiou, Organometallics 2008, 27, 497
65. Z. Du, W. Li, X. Zhu, F. Xu, Q. Shen, J. Org. Chem. 2008, 73, 8966
66. W. X. Zhang, M. Nishiura, Z. Hou, Chem. Eur. J. 2007, 13, 4037
67. Q. Li, S. Wang, S. Zhou, G. Yang, X. Zhu, Y. Liu, J. Org. Chem. 2007, 72, 6763
68. T. G. Ong, J. S. O'Brien, I. Korobkov, D. S. Richeson, Organometallics 2006, 25, 4728
69. H. Shen, H. S. Chan, Z. Xie, Organometallics 2006, 25, 5515
70. F. Montilla, D. del Río, A. Pastor, A. Galindo, Organometallics 2006, 25, 4996
71. W. X. Zhang, M. Nishiura, Z. Hou, Chem. Commun. 2006, 3812
72. W. X. Zhang, M. Nishiura, Z. Hou, Synlett 2006, 1213
73. W. X. Zhang, M. Nishiura, Z. Hou, J. Am. Chem. Soc. 2005, 127, 16788
74. T. G. Ong, G. P. A. Yap, D. S. Richeson, J. Am. Chem. Soc. 2003, 125, 8100.
75. T. G. Ong, G. P. A. Yap, D. S. Richeson, Chem. Commun. 2003, 2612
76. R. L. Zuckerman, R. G. Bergman, Organometallics 2000, 19, 4795.
77. K. Hartke, E. Palou, Chem. Ber. 1966, 99, 3155
78. W. T. Brady, R. A. Owens, J. Org. Chem. 1977, 42, 3220.
79. X. Xu, J. Gao, D. Cheng, J. Li, G. Qiang, H. Guo, Adv. Synth. Catal. 2008, 350, 61.
80. J. Rouden, A. Ragot, S. Gouault, D. Cahard, J. C. Plaquevent, M. C. Lasne, Tetrahedron: Asymmetry 2002, 13, 1299.
81. M. Skwarczynski, Y. Kiso, Curr. Med. Chem. 2007, 14, 2813
82. N. Marion, S. P. Nolan, Angew. Chem. 2007, 119, 2806
83. Angew. Chem. Int. Ed. 2007, 46, 2750.
84. Z. Zhang, Y. Liu, M. Gong, X. Zhao, Y. Zhang, J. Wang, Angew. Chem. 2010, 122, 1157
85. Angew. Chem. Int. Ed. 2010, 49, 1139
86. G. Li, X. Huang, L. Zhang, Angew. Chem. 2008, 120, 352
87. Angew. Chem. Int. Ed. 2008, 47, 346
88. Z. Liu, F. Shi, P. D. G. Martinez, C. Raminelli, R. C. Larock, J. Org. Chem. 2008, 73, 219
89. B. M. Trost, D. R. Fandrick, T. Brodmann, D. T. Stiles, Angew. Chem. 2007, 119, 6235
90. Angew. Chem. Int. Ed. 2007, 46, 6123
91. T. Miura, M. Shimada, M. Murakami, Angew. Chem. 2005, 117, 7770
92. Angew. Chem. Int. Ed. 2005, 44, 7598
93. T. Shimada, I. Nakamura, Y. Yamamoto, J. Am. Chem. Soc. 2004, 126, 10546.
94. E. A. Pritchina, N. P. Gritsan, G. T. Burdzinski, M. S. Platz, J. Phys. Chem. A 2007, 111, 10483
95. T. Yatsunami, S. Iwasaki, Helv. Chim. Acta 1978, 61, 2823
96. M. Franck-Neumann, C. Dietrich-Buchecker, Tetrahedron Lett. 1976, 17, 2069
97. J. W. Meyer, G. S. Hammond, J. Am. Chem. Soc. 1972, 94, 2219.