Domino reaction of acyclic α,α-dialkenoylketene S,S-acetals and diamines: Efficient synthesis of tetracyclic thieno[2,3-2b]-thiopyran-fused imidazo[1,2-a]pyridine/pyrido[1,2-a]pyrimidines

Advanced Synthesis and Catalysis

Volumn 348, Issue 14, 2006, Pages 1986-1990

  Liang, Fushun ^a   Zhang, Jiqing ^a   Tan, Jing ^a   Liu, Qun ^a  

^a NORTHEAST NORMAL UNIVERSITY   (China)

Author keywords

, dialkenoylketene S,S acetals; Diamines; Domino reactions; Fused polyheterocycles

Indexed keywords

EID: 33749350169     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200606134     Document Type: Article

References (64)

1. Reviews: a) L. F. Tiete, Chem. Rev. 1996, 96, 115-136;
2. b) S. E. Denmark, A. Thorarensen, Chem. Rev. 1996, 96, 137-165;
3. c) M. Malacria, Chem. Rev. 1996, 96, 289-306;
4. d) P. J. Parsons, C. S. Penkett, A. J. Shell, Chem. Rev. 1996, 96, 195-206;
5. e) K. Neuschütz, J. Velker, R. Neier, Synthesis 1998, 227-255;
6. f) G. Poli, G. Giambastiani, A. Heumann, Tetrahedron 2000, 56, 5959-5989;
7. g) A. J. McCarroll, J. C. Walton, Angew. Chem. 2001, 113, 2282-2307;
8. Angew. Chem. Int. Ed. 2001, 40, 2224-2248;
9. h) L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 134-170;
10. Angew. Chem. Int. Ed. 1993, 32, 131-163;
11. i) A. Bunce, Tetrahedron 1995, 51, 13103-13159;
12. k) K. C. Nicolaou, T. Montagnon, S. A. Snyder, Chem. Commun. 2003, 551-564;
13. j) A. de Meijere, P. von Zezschwitz, S. Erase, Acc. Chem. Res. 2005, 38, 413-422.
14. a) S. A. A. El Bialy, H. Braun, L. F. Tietze, Angew. Chem. 2004, 116, 5505-5507;
15. Angew. Chem. Int. Ed. 2004, 43, 5391-5393;
16. b) H. Neumann, A. J. von Wang-gelin, S. Klaus, D. Strübing, D. Gördes, M. Beller, Angew. Chem. 2003, 115, 4641-4645;
17. Angew. Chem. Int. Ed. 2003, 42, 4503-4507;
18. c) J. A. González-Vera, M. T. García-López, R. Herranz, Org. Lett. 2004, 6, 2641-2644;
19. d) G. Cuny, M. Bois-Choussy, J. Zhu, Angew. Chem. 2003, 115, 4922-4925;
20. Angew. Chem. Int. Ed. 2003, 42, 4774-4777;
21. e) G. Giorgi, S. Miranda, P. López-Alvarado, C. Avendaño, J. Rodriguez, J. Carlos Menéndez, Org. Lett. 2005, 7, 2197-2200;
22. f) C. H. Heathcock, Angew. Chem. 1992, 104, 675;
23. Angew. Chem. Int. Ed. Engl. 1992, 31, 665-681.
24. B. M. Trost, Science 1991, 254, 1471.
25. B. Alcaide, P. Almendros, Curr. Med. Chem. 2004, 11, 1921-1949.
26. Reviews: a) R. K. Dieter, Tetrahedron 1986, 42, 3029-3096;
27. b) H. Junjappa, H. Ila, C. V. Asokan, Tetrahedron 1990, 46, 5423-5506;
28. c) H. Tla, H. Junjappa, O. Barun, J. Organometal. Chem. 2001, 624, 34-40.
29. a) Y. Yin, M. Wang, Q. Liu, J. Hu, S. Sun, J. Kang, Tetrahedron Lett. 2005, 46, 4399-4402;
30. b) S. Sun, Q. Zhang, Q. Liu, J. Kang, Y. Yin, D. Li, D. Dong, Tetrahedron Lett. 2005, 46, 6271-6274;
31. c) D. Dong, Y. Liu, Y. Zhao, Y. Qi, Z. Wang, Q. Liu, Synthesis 2005, 85-91;
32. d) Q. Liu, G. Che, H. Yu, Y. Liu, J. Zhang, Q. Zhang, D. Dong, J. Org. Chem. 2003, 68, 9148-9150;
33. e) Y. Liu, D. Dong, Q. Liu, Y. Qi, Z. Wang, Org. Biomol. Chem. 2004, 2, 28-30;
34. f) S. Sun, Y. Liu, Q. Liu, Y. Zhao, D. Dong, Synlett 2004, 1731-1734;
35. g) Y.-L. Zhao, Q. Liu, J.-P. Zhang, Z.-Q. Liu, J. Org. Chem. 2005, 70, 6913-6917.
36. a) R. Samuel, S. K. Nair, C. V. Asokan, Synlett 2000, 1804-1806;
37. b) B. K. Joseph, B. Verghese, C. Sudarsanakumar, S. Deepa, D. Viswam, P. Chandran, C. V. Asokan, Chem. Commun. 2002, 736-737;
38. c) X. Bi, Q. Liu, S. Sun, J. Liu, W. Pan, L. Zhao, D. Dong, Synlett 2005, 49-54.
39. a) X. Bi, D. Dong, Q. Liu, W. Pan, L. Zhao, B. Li, J. Am. Chem. Soc. 2005, 127, 4578-4579;
40. b) D. Dong, X. Bi, Q. Liu, F. Cong, Chem. Commun. 2005, 3580-3582;
41. c) X. Bi, D. Dong, Y. Li, Q. Liu, J. Org. Chem. 2005, 70, 10886-10889;
42. d) L. Zhao, F. Liang, X. Bi, S. Sun, Q. Liu, J. Org. Chem. 2006, 71, 1094-1098.
43. a) M. Wang, X. Xu, Q. Liu, L. Xiong, B. Yang, L. Gao, Synth. Comm. 2002, 32, 3437-3443;
44. b) E. B. Choi, I. K. Youn, C. S. Pak, Synthesis 1991, 15-18.
45. See Supporting Information.
46. 2 = 0.1766 (all data). CCDC 271744 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data request/cif.
47. a) G. S. Ponticello, M. B. Freedman, C. N. Habecker, P. A. Lyle, H. Schwam, S. L. Varga, M. E. Christy, W. C. Randall, J. J. Baldwin, J. Med. Chem. 1987, 30, 591-597;
48. b) G. D. Hartmann, W. Halczenko, J. D. Prugh, R. L. Smith, M. F. Sugrue, P. J. Mallorga, S. R. Michelson, W. C. Randall, H. Schwam, J. M. Sondey, J. Med. Chem. 1992, 35, 3027-3033;
49. c) J. J. Baldwin, G. S. Ponticello, G. S. Anderson, M. E. Christy, M. A. Murcko, W. C. Randall, H. Schwam, M. F. Sugrue, J. B. Springer, P. Gautheron, J. Grove, P. Mallorga, M. P. Viader, B. M. McKeever, M. A. Navia, J. Med. Chem. 1989, 32, 2510-2513.
50. a) G. Trapani, M. Franco, L. Ricciardi, A. Latrofa, G. Genchi, E. Sanna, F. Tuveri, E. Cagetti, G. Biggio, G. Liso, J. Med. Chem. 1997, 40, 3109;
51. b) C. Hamdouchi, J. del Bias, M. del Prado, J. Gruber, B. A. Heinz, L. Vance, J. Med. Chem. 1999, 42, 50;
52. c) A. Gangjee, O. Adair, S. F. Queener, J. Med. Chem. 1999, 42, 2447;
53. d) A. Gangjee, O. Adair, S. F. Queener, J. Med. Chem. 2003, 46, 5074;
54. e) A. Gangjee, O. Adair, S. F. Queener, Bioorg. & Med. Chem. 2001, 9, 2929.
55. C. F. Bernasconi, Tetrahedron 1989, 45, 4017-4090.
56. V. A. Ogurtsov, O. A. Rakitin, C. W. Rees, A. A. Smolentsev, P. A. Belyakov, D. G. Golovanov, K. A. Lyssenko, Org. Lett. 2005, 7, 791-794.
57. S. K. Nair, R. Samuel, C. V. Asokan, Synthesis 2001, 4, 573-576.
58. Examples of 6π-azaelectrocyclization: a) K. Tanaka, S. Katsumura, J. Am. Chem. Soc. 2002, 124, 9660-9661;
59. b) K. Tanaka, S. Katsumura, Org. Lett. 2000, 2, 373-375;
60. c) K. Tanaka, T. Kobayashi, H. Mori, S. Katsumura, J. Org. Chem. 2004, 69, 5906-5925;
61. d) K. Tanaka, H. Mori, M. Yamamoto, S. Katsumura, J. Org. Chem. 2001, 66, 3099-3110;
62. e) M. Alajarin, Maria-Mar Ortin, Pilar Sánchez-Andrada, Ángel Vidal, Delia Bautista, Org. Lett. 2005, 7, 5281-5284;
63. f) A. R. deLera, W. Reischl, W. H. Okamura, J. Am. Chem. Soc. 1989, 111, 4051-4063;
64. g) D. F. Maynard, W. H. Okamura, J. Org. Chem. 1995, 60, 1763-1771.