One-pot synthesis of polyfunctionalized 4H-chromenes and dihydrocoumarins based on copper(II) bromide-catalyzed C-C coupling of benzylic alcohols with ketene dithioacetals

Advanced Synthesis and Catalysis

Volumn 352, Issue 10, 2010, Pages 1593-1599

  Liang, Deqiang ^a   Wang, Mang ^a,b   Bekturhun, Bahargul ^a   Xiong, Binbin ^a   Liu, Qun ^a  

^a NORTHEAST NORMAL UNIVERSITY   (China)

^b DALIAN UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

C c coupling; Chromenes; Copper; Cyclization; Dihydrocoumarins

Indexed keywords

EID: 77954810502     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000062     Document Type: Article

References (60)

1. a) G. P. Ellis, in: The Chemistry of Heterocyclic Compounds Chromenes, Chromanes and Chromones, (Eds.: A. Weissberger, E. C. Taylor), John Wiley, New York, 1977, pp 11-139, Chapter II;
2. b) A. A. M. Eissa, N. A. H. Farag, G A. H. Soliman, Bioorg. Med. Chem. 2009, 17, 5059-5070;
3. c) R. Amin, B. Krammer, N. Abdel-Kader, T. Verwanger, A. El-Ansary, Eur. J. Med. Chem. 2010, 45, 372-378.
4. a) E. J. Corey, L. I. Wu, J. Am. Chem. Soc. 1993, 115, 9327-9328;
5. b) A. G. Martinez, L. J. Marco, Bioorg. Med. Chem. Lett. 1997, 7, 3165-3170;
6. c) W. P. Smith, L. S. Sollis, D. P. Howes, C. P. Cherry, D.I. Starkey, N. K. Cobley, J. Med. Chem. 1998, 41, 787-797;
7. d) J.-L. Wang, D. X. Liu, Z.-J. Zhang, S. M. Shan, X. B. Han, S. M. Srinivasula, C. M. Croce, E. S. Alnemri, Z. W Huang, Proc. Natl. Acad. Sci. USA 2000, 97, 7124-7129;
8. e) D. R. Anderson, S. Hegde, E. Reinhard, L. Gomez, W. F. Vernier, L. Lee, S. Liu, A. Sambandam, P. A. Snider, L. Masih, Bioorg. Med. Chem. Lett. 2005, 15, 1587-1590;
9. f) F. Shaheen, M. Ahmad, S. N. Khan, S. S. Hussain, S. Anjum, B. Tashkhodjaev, K. Turgunov, M. N. Sultankhodzhaev, M. I. Choudhary, A. Rahman, Eur. J. Org. Chem. 2006, 2371-2377;
10. g) S. Sciabola, E. Carosati, L. Cucurull-Sanchez, M. Baroni, R. Mannhold, Bioorg. Med. Chem. 2007, 15, 6450-6462;
11. h) S. X. Cai, J. Drewe, W. Kemnitzer, Anti-Cancer Agents in Med. Chem. 2009, 9, 437-456;
12. i) M. Gao, M. Wang, K. D. Miller, G. D. Hutchins, Q.-H. Zheng, Appl. Radiat. Isot. 2010, 68, 110-116.
13. a) E. A. Hafez, M. H. Elnagdi, A. G. A. Elagemey, F. M. A. A. El-Taweel, Heterocycles 1987, 26, 903-907;
14. b) M. S. Al-Thebeiti, Heterocycles 1999, 57, 1765-2774;
15. c) J. R. Li, L. J. Zhang, X. Q. Yang, Q. Li, D. Wang, C. X. Wang, D. X. Shi, Q. Zhang, Chin. Chem. Lett. 2008, 19, 15-18.
16. a) Y.-L. Shi, M. Shi, Org. Lett. 2005, 7, 3057-3060;
17. b) G.-L. Zhao, Y-L. Shi, M. Shi, Org. Lett. 2005, 7, 4527-4530;
18. c) Y.-L. Shi, M. Shi, Chem. Eur. J. 2006, 12, 3374-3378;
19. d) Y.-L. Shi, M. Shi, Org. Biomol. Chem. 2007, 5, 1499-1504;
20. e) X. Zhang, S. Zhang, W. Wang, Angew. Chem. 2010, 122, 1523-1526;
21. Angew. Chem. Int. Ed. 2010, 49, 1481-1484.
22. a) J. S. Yadav, B. V. Subba Reddy, M. K. Gupta, I. Prathap, S. K. Pandey, Catal. Commun. 2007, 8, 2208-2211;
23. b) M. Costa, F. Areias, L. Abrunhosa, A. Venâncio, F. Proença, J. Org. Chem. 2008, 73, 1954-1962;
24. c) M. N. Elinson, A. S. Dorofeev, F. M. Miloserdov, A. I. Ilovaisky, S. K. Feducovich, P. A. Belyakov, G. I. Nikishin, Adv. Synth. Catal. 2008, 350, 591-601.
25. a) Y. Nishibayashi, Y. Inada, M. Hidai, S. Uemura, J. Am. Chem. Soc. 2002, 124, 7900-7901;
26. b) W. A. L. V. Otterlo, E. L. Ngidi, S. Kuzvidza, G. L. Morgans, S. S. Moleele, C. B. Koning, Tetrahedron 2005, 61, 9996-10006;
27. c) Y. W Fang, C. Z. Li, J. Org. Chem. 2006, 71, 6427-6431;
28. d) J. Fan, Z. Wang, Chem. Commun. 2008, 5381-5383.
29. a) C.-J. Li, Acc. Chem. Res. 2002, 35, 533-538;
30. b) B. M. Trost, F. D. Toste, A. B. Pinkerton, Chem. Rev. 2001, 101, 2067-2096;
31. c) S. R. Chemler, D. Trauner, S. J. Danishefsky, Angew. Chem. 2001, 113, 4676-4701;
32. Angew. Chem. Int. Ed. 2001, 40, 4544-4568;
33. d) K. C. Nicolaou, P. G. Bulger, D. Sarlah, Angew. Chem. 2005, 117, 4516-4663;
34. Angew. Chem. Int. Ed. 2005, 44, 4442-4489.
35. a) M. Shibasaki, M. Kanai, Chem. Rev. 2008, 108, 2853-2873;
36. b) A. Alexakis, J. E. Bäckvall, N. Krause, O. Pàmies, M. Diéguez, Chem. Rev. 2008, 108, 2796-2823.
37. For selected examples, see: a) M. Wang, F. Han, H. Yuan, Q. Liu, Chem. Commun. 2010, 46, 2247-2249;
38. b) J. Tan, X. Xu, L. Zhang, Y. Li, Q. Liu, Angew. Chem. 2009, 121, 2912-2916;
39. Angew. Chem. Int. Ed. 2009, 48, 2868-2872;
40. c) X. Bi, D. Dong, Q. Liu, W. Pan, L. Zhao, B. Li, J. Am. Chem. Soc. 2005, 127, 4578-4579;
41. d) Z. Fu, M. Wang, Y Ma, Q. Liu, J. Liu, J. Org. Chem. 2008, 73, 7625-7630;
42. e) Y. Ma, M. Wang, D. Li, B. Bekturhun, J. Liu, Q. Liu, J. Org. Chem. 2009, 74, 3116-3121.
43. a) H.-J. Yuan, M. Wang, Y.-J. Liu, Q. Liu, Adv. Synth. Catal. 2009, 357, 112-116, and references cited therein;
44. b)Y. Liu, M. Wang, H. Yuan, Q. Liu, Adv. Synth. Catal. 2010, 352, 884-892;
45. c) Y. Yin, M. Wang, Q. Liu, J. Hu, S. Sun, J. Kang, Tetrahedron Lett. 2005, 46, 4399-4402;
46. d) Q. Zhang, S. Sun, J. Hu, Q. Liu, J. Tan, J. Org. Chem. 2007, 72, 139-143.
47. a) M. Yasuda, T. Somyo, A. Baba, Angew. Chem. 2006, 118, 807-810;
48. Angew. Chem. Int. Ed. 2006, 45, 793-796;
49. b) K. Motokura, N. Fujita, K. Mori, T. Mizugaki, K. Ebitani and K. Kaneda, Angew. Chem. 2006, 118, 2667-2671;
50. For selected examples on the biological activities of dihydrocoumarins, see: a) F. Roelens, K. Huvaere, W. Dhooge, M. Van Cleemput, F. Comhaire, D. De Keukeleire, Eur. J. Med. Chem. 2005, 40, 1042-1051;
51. b) X. Zhang, H. Wang, Y Song, L. Nie, L. Wang, B. Liu, P. Shen, Y Liu, Bioorg. Med. Chem. Lett. 2006, 16, 949-953;
52. c) K. Takara, A. Kuniyoshi, K. Wada, K. Kinjyo, H. Iwasaki, Biosci. Biotechnol. Biochem. 2008, 72, 2191-2194.
53. For recent reports on the synthesis of 3,4-disubstituted dihydrocoumarins, see: a) S. Duan, R. Jana, J. A. Tunge, J. Org. Chem. 2009, 74, 4612-4614;
54. b) E. Alden-Danforth, M. T. Scerba, T. Lectka, Org. Lett. 2008, 10, 4951-4953;
55. c) A. Shaabani, E. Soleimani, A. H. Rezayan, A. Sarvary, H. R. Khavasi, Org. Lett. 2008, 10, 2581-2584;
56. d) H. Lv, L. You, S. Yea, Adv. Synth. Catal. 2009, 351, 2822-2826;
57. e) X. Han, X. Lu, Org. Lett. 2010, 12, 108-111.
58. In all cases except entries 8-12, the coupling product A, generated from 2a and methanethiol, was always obtained in 20-40% yields (yield based on la) along with the isolation of 477-chromene 3a. (Figure Presented)
59. 2 for 10 min at reflux (Table 2, entry 12).
60. 2. Its spectroscopic data are included in the Supporting Information. . (Figure Presented)